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The Perfect Oregon Road Trip Itinerary – 7 or 10 days

Last updated on June 9th, 2024 at 12:35 pm

Oregon (pronounced “Ore-gun”, not “Ore-gone”!) is often overshadowed by its extremely popular neighboring state of California in the US. But if you are looking for a road less traveled then you have to take an Oregon road trip. In this blog post, we will share our detailed itinerary including what to see, do, and where to stay.

Below is a map of the route we took on this trip, click here to go to Google Maps. We drove across the state in a clockwise direction but you can do the same in an anti-clockwise direction as well. If you remember we did a similar 7-day road trip in Iceland and trust me when I say that our Oregon road trip was just as adventurous. Don’t forget to check out our post on waterfalls near Portland for more incredible inspiration.

FUN FACT: Oregon is the only other state in the US after New Jersey to have assistants at gas stations to fill gas in your car.

How Many Days Do You Need for an Oregon Road Trip?

We were able to make this a total of the 10-day trip including travel time. If you follow our Oregon itinerary you will have plenty of time to go on hikes, take wine tours, and relax on this road trip.

You can easily make this a 7-day road trip and we’ll tell you how in the modified itinerary below. However, if you have less than 7-days then I suggest visiting only Portland, Columbia River Gorge, Mt. Hood region, & Cannon Beach from the itinerary below.

Disclaimer: This post contains affiliate links.

Related Read: SF to LA – An ultimate west coast road trip guide

Starting point 

We flew into Portland and spend 2 days in the city before starting our road trip. TIP: You do not need a car in Portland city so save yourselves some cash by renting a car the day you hit the road.

Portland would be our recommendation as a starting point for all those who are flying into Oregon. For those who are driving from the South i.e. California, the best starting point for you would be either the coast or Crater lake in this loop.

Oregon Road Trip Itinerary

Below is our detailed itinerary is broken out by each day. If you want to do a 7-day road trip then we have listed where it makes the most sense to skip things.

Day 1 & 2 – Portland

After you land in Portland spend 2 days in this funky city. We not only explored the city landmarks but in reality spend the entire weekend food binging in Portland. TIP: If you want to make this a 7-day road trip then spend just 1 day in Portland.

We will be writing a separate post on what to do on a weekend in Portland. But to highlight a few things –

• Eat your heart out in the food capital on the west coast. From food trucks to delicious worldwide cuisines all around town you’re going to return with some additional baggage on your body.
• Check out the largest bookstore in the world – Powell’s Bookstore
• Must eat doughnuts (try both Bluestar & Vodoo doughnuts to give your own verdict no matter what the locals say)
• Take a walking city tour or a Segway tour to learn more about the city
• Check out the Japanese Garden

ACCOMMODATION: It usually nice if you stay in either downtown or the pearl district so you’re walking distance away from all the things –

• Hilton Portland Downtown or the Hampton Inn Pearl District
• The Bidwell Marriott Portland or the Courtyard Marriott City Center

More Places to Stay in Portland, Oregon

Harlow Hotel

Inn at Northrup Station

Day 3 – Columbia River Gorge Waterfalls & wineries

Fasten your seatbelts and drive to the Columbia River Gorge which is only 30 minutes away from Portland. If you start driving early in the morning, you’ll easily be able to cover all the stopovers mentioned below in that order. For more details, read our in-depth blog post on Columbia Gorge road trip .

• Portland Women’s Forum vista point (has the best sunrise view if there are no wildfire smoke)
• Latourell Falls (add a short 2.4 mile hike here)
• Multnomah Falls
• Bridal Veil Falls (add a short 1.2 mile hike here)
• Starvation Creek Falls
• Wineries tour in Mt. Hood/Gorge

ACCOMMODATION: Spend the night in White Salmon, WA or Hood River, OR

Find fun things to do in Oregon during your road trip!

Day 4 – Explore Mt. Hood Region

We spent 2 nights in Mt. Hood region which gave us the time to not only explore but also relax in the most gorgeous setting. There are a ton of outdoor activities to do here so spending only 1 day would be an injustice to this region. We have broken down the activities by each day for you –

• Explore Hood River town which is known as the world’s kite surfing capital, perhaps indulge in some water activity or grab lunch here
• The Gorge White House makes for a great stop for Apple cider tasting and fresh fruit & flower farm
• If you happen to visit in spring don’t forget to check out the “ fruit loop ” trails for spring blossoming trees .
• Drive to the historic Timberline Lodge and either take the chair lift to get to the summit or if you are up for an adventure there are tons of hiking trails behind the lodge. We did a section of the zigzag overlook trail which starts at the lodge parking area. Ask the lodge visitor center for more info on trails. Enjoy a nice early dinner or a cup of coffee with a view.
• If you are not up for visiting the lodge then consider hiking the Mirror Lake loop trail that afternoon. We skipped the mirror lake loop.
• Return to Government Camp for dinner unless you are staying back at Timberline Lodge.

ACCOMMODATION: Spend the night in Mt. Hood region. We stayed in a gorgeous farmhouse surrounded by apple & pear orchards booked through Airbnb . Your other best option is to stay at the historic  Timberline Lodge or hotels in Government Camp , a small town in Mt. Hood region.

Day 5 – Explore Mt. Hood Region

Here’s what to do on your second day in Mt. Hood region –

• Hit the Tamanawas Falls hiking trail in the morning (alternatively, you can do the Mirror Lake loop). Tamanawas trail is amazing, take our word for it.
• Have your lunch at Tamanawas Falls. Pack your lunch with you so you can eat with the waterfall views at the end of the hike.
• After lunch head to Trillium Lake in the afternoon. Walk along the lake trail or rent a kayak and enjoy the serene Mt Hood view from the water. TIP: Book your kayak rental in Govt Camp as there are no rental facilities at Trillium lake. The rental company will bring your kayak to the lake area. Don’t miss the sunset at Lake Trillium!  TIP: Bring mosquito spray, there are like a thousand of them here. You can also rent campgrounds at Trillium lake if you want to camp in this area.

ACCOMMODATION: We stayed back at the same farmhouse Airbnb with the perfect view of Mt. Hood. Your other best option is to stay at the historic  Timberline Lodge or hotels in Government Camp , a small town in Mt. Hood region.

Day 6 – Smith Rock State Park, Painted Hills & 3 Sisters

As you drive south from Mt. Hood, take a day to explore the desert region of Oregon. You’d be surprised to know that a big part of Oregon is, in fact, desert land. What was really fascinating to us was that our families in India instantly knew about Oregon out of all the places. They were the ones to tell us about Rajneeshpuram.  FACT: Rajneeshpuram (from ‘Wild Wild Country’ series on Netflix) was not too far from this part of Oregon.

TIP: For a 7-day Oregon road trip, skip this section and head straight to Crater Lake from Mt. Hood.

• Stop at Smith Rock State Park as you drive south from Mt. Hood region. and enjoy the gorgeous scenery.
• Drive about 2 hours east to see the Painted Hills which are in the deep end of the Oregonian desert.
• Reach Bend and head to Summit Park for a great view of the 3 Sisters volcano peaks .
• If you want to get a better view of 3 sisters then drive 30 mins from Bend to Dutchman Flat Sno Park in Deschutes National Forest.

ACCOMMODATION: Spend the night in Bend, OR .

Where to Stay in Bend, Oregon

Element Bend

Campfire Hotel

Holiday Inn Express & Suites

Day 7 – Crater Lake National Park

Crater Lake National Park is about 2 hours away from Bend or about 4 hours from Govt Camp. If you leave early in the morning, you can reach Crater Lake just in time to drive around the rim and see the following viewpoints & sneak in one easy hike.

Pick and choose your favorite spots to see in Crater Lake National Park , below are a few that we recommend –

• Sinnott Memorial Outlook at Rim Visitor Center
• Sun Notch (0.8 miles easy hike with views of Phantom Ship)
• Phantom ship overlook
• Discovery Point (2 miles)
• Watchman Peak (1.6 miles moderate steep hike)
• Pumice castle overlook,
• Cloudcap overlook,
• Vidae Falls
• Pinnacles Overlook.

ACCOMMODATION: Spend the night in Crater Lake Lodge or campgrounds in the park . If you don’t get a reservation in either of these then consider staying in Fort Klamath or Chemult or Chiloquin which are small towns near Crater Lake. TIP: If you stay at Crater Lake Lodge, then don’t miss the splendid sunset from the lobby’s back patio.

PLEASE NOTE:   The Crater Lake itinerary was a part of our original plan until west coast wildfires & smoke completely ruined the experience. When we arrived at Crater Lake National Park, it became really difficult to breathe without inhaling the fumes. Not to mention, the visibility of the Lake was near zero. We had booked a campground for the night but for good reasons we decided to turn around. As a backup plan, we headed to spend more time on the Oregon coast. PRO   TIP: Watch out for wildfire and smoke reports in Oregon before you head here!

Day 8 – Umpqua National Forest & drive to Eugene

Next morning stop by the Crater Lake vista points that you might’ve missed on the previous day. On your way to the coast of Oregon, you must take a pitstop at Umpqua National Forest for a bonus waterfall & hidden hot springs.

• Drive around Crater Lake in the morning to cover any missed vista points from the previous day.
• Hike the  Toketee Waterfall trail in Umpqua National Forest as you exit Crater Lake. It’s an easy 0.8 miles round trip hike to the gorgeous waterfalls as you can see in our photos.
• If you enjoy natural hot springs , then as you exit from Toketee waterfalls take a left and head to Umpqua Hot Springs . There is a $5/vehicle charge to park at the hot springs. Clothing is not enforced here so consider yourself forewarned. In full disclosure, we did not visit the hot springs due to a lack of time.
• Drive to Eugene from Toketee Falls should take around 2.30 hrs.

ACCOMMODATION: Spend the night in Eugene, OR .

Where to Stay in Eugene, Oregon

Comfort Suites Eugene

Maverick Hotel

Graduate Eugene

Day 9:  Oregon Coast road trip

The next morning we headed to Florence from Eugene where we started our Oregon coast drive. The coastal drive takes you on Highway 101 which, in fact, is a continuation of California’s coast to Oregon’s.

Given that we just had one day set aside for this Oregon coast road trip, we only stopped at the vista points mentioned below in bold. We’ve listed some additional awesome pit stops along the way if you have more time.

• Drive past Florence 
• Heceta Head Lighthouse  Scenic Viewpoint (There is a B&B at this lighthouse now) or stop at Sea Lion vista point to see the lighthouse from a distance.
• Cape Perpetua Overlook (Thor’s Well is another stop before turning right to Cape Perpetua overlook)
• Yachats (stop by for a drink or early lunch)
• Newport (If you skip Yachats then stop here for lunch)
• Devil’s punchbowl and Otter Rock
• Tillamook (stop by at the cheese factory or the Tillamook ice-creamery)
• Cannon Beach, get here before sunset to watch the magic unfold

ACCOMMODATION: Spend the night in Cannon Beach, OR .

Day 10: Lewis & Clark National Park OR Evergreen Aviation Museum

We took a red-eye back to the east coast since we wanted to squeeze every second of our last day. TIP: For a 7-day Oregon road trip, skip this part and fly out on your last day.

• We visited the Evergreen Aviation & Space Museum in the morning but you can choose to visit the Lewis & Clark National Park near Cannon Beach to get an insight into expeditions that were an integral part of US history.
• Head back to Portland to grab an early dinner before heading out to the airport for an evening flight.

Phew, another long guide, isn’t it? But there is so much to see & do here that you have to plan it right and we’ve to give all the right info to do so. And by the way, if Oregon wasn’t on your list, we sure hope it is now!

If you liked this extensive Oregon road trip planning guide then don’t forget to share it along with family & friends.

More on Travel in the United States:

• America’s favorite road trip – the Blue Ridge Parkway
• Bucket List Arizona Road Trip – The perfect long weekend 4-day itinerary
• Best places to see fall colors in New Hampshire – A Roadtrip through New England
• Ultimate SF to LA Road trip – Best stops along California’s Pacific Coast Highway

Happy Traveling!

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23 comments on “ the perfect oregon road trip itinerary – 7 or 10 days ”.

Such a detailed guide. Thanks for sharing! Perhaps this fall my family and I will go to the Oregon. Awesome photos!

Thanks Michael. Hopefully the fires will be in control by then and the smoke out of OR skies. This year the wildfires have been terrible for Oregon.

Wow you really packed a lot in to tour trip. As someone who lives in Oregon, this is a great post. Come back soon!

We would love to!!! 😀

Wow! Mind blowing and eye catching photography. All places are just awesome. Hope to trip to those places in the near future. Stunning! You must (please) take me there when I visit. Thanks for sharing such a beautiful place.

You are most welcome and hope you visit Oregon someday 🙂

We did a Northern California road trip in June last year and did a tiny bit of Oregon so that we could try some of the wineries up there. I wish we’d done more of Oregon because it looks amazing and I’m filing your post for our next trip!

There’s always a next time 🙂

I’ve never visited the northwest USA but I really have to get there asap, this road trip looks amazing! 🙂

Yeah the Pacific Northwest is truly magical 🙂

Wow, great itinerary! I hope to come back to USA next year and was just looking into California and neighboring states for potential road trip ideas. Oregon looks an idea place to visit! Love the nature and national parks

Oh yes definitely visit OR if you are coming to CA, you will love it! 🙂

Oregon is such a beautiful state, I can’t wait to spend more time there. This looks like a really good way to see a lot of the state in one well, a great itinerary. I live in Vancouver Canada so this is such a doable trip for me

Oh yeah, definitely easily doable from Vancouver. I believe there is an easy train ride from Seattle to Portland, wonder if there is a train from Vancouver to Portland as well?!

I love a good road trip! Thanks for sharing these great places in Oregon 🙂

Most welcome! There’s nothing like sharing cool places to do a great road trip. 😀

We did a similar trip a few years ago, but looks like we missed the Umpqua National Forest. Oh well! Looks like we just need to head back.☺️ Thanks for the post!

You’ve got to leave something out to return back to such amazing places right?! 😉

I had no idea Oregon was this beautiful! I love the suggestion of seeing the state through a road trip, definitely saving for later 🙂

Yeah, this is one of the perfect States to visit in one road trip 🙂

There is obviously plenty to do in Oregon. My personal goals for almost any trip is to do lots of hiking and visit lots of breweries and wineries. I didn’t know that you could have your gas filled by station attendants there. I think I might plan a trip there for that alone. It would be so cool!

It’s great to learn that you should stay downtown when going on a trip to Portland. My wife and I are looking to travel to Oregon soon and we were wondering where we should stay at in the state. I’ll be sure to let my wife know that we can stay in downtown Portland.

Oh yes, Portland is so close to a lot of nature in Oregon. However, if you want to do a road trip around the entire State then as mentioned above you might have to pick other cities for overnight stay esp when going down south or east.

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Hello from Gaurav & Richa! An adventurous couple who did NOT quit their corporate jobs to travel the world. On the contrary, we're all about balancing that work-travel life. Our goal is to explore as much as we can in our short vacations and yes, we do go to great lengths to find unique experiences and great food to share with you all. Learn more About Us .

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The Complete Oregon Road Trip Itinerary (50 Stops & 4 Unique Routes!)

Post Summary: The Ultimate Oregon Road Trip Itinerary According To A PNW Local

Oregon. That magical spot in the corner of the United States where roaring waterfalls, epic coastlines, and mysteries in the forest all thrive next to each other. 

It’s an incredible place that requires the guidance of PNW experts (that’s us!) to divulge all the best stops in the state. We’ve been exploring Oregon for years , so you can count on us to provide well-rounded tips to give you the best experience!

In this post, we’re sharing the most epic Oregon road trip route , including our favorite stops and custom trips of 2-weeks, 10-days, and 1-week to cater to your specific needs. Scroll all the way to the bottom to find a free Oregon road trip itinerary download , too!

Okay, enough talking, let’s get exploring!

The Ultimate Oregon Road Trip Itinerary (Exactly Where To Find The Best Spots!)

First of all, where is oregon.

Oregon is located in a region called the Pacific Northwest , which is located in the northwest corner of the contiguous United States.

Fixed between its northern neighbor, Washington , and its southern neighbor, Northern California , Oregon is a unique mix of giant redwood trees, raging waterfalls, high desert, and beautiful coastal wilderness.

It’s got a little bit of everything , which is why taking an Oregon road trip will probably be the most incredible thing you will do this year!

Here’s a little bit about Oregon to start…

Oregon is broken down into seven distinct regions, each with its own unique spin on Oregon culture and iconic destinations . Here’s a breakdown of what you might expect from each:

• The Oregon Coast: 363 miles of accessible beaches, historic lighthouses, sea stacks, and gorgeous little Oregon beach towns . 
• Central Oregon: A High Desert escape including popular spots like Sisters, Bend, and Smith Rock State Park . 
• Eastern Oregon : Lonely vast desert with incredible geological features scattered across the area. Known for the Alvord Desert, Pendleton, and the Painted Hills. 
• Portland Region: The urban center for creatives, makers, and foodies. Known for its epic food culture, bridges, and accessibility to nature.
• Mt. Hood & The Columbia River Gorge: Home to the highest mountain in Oregon (Mt Hood), and some of the most famous Oregon waterfalls like Multnomah Falls. 
• Southern Oregon: Home to Crater Lake National Park, this region also boasts adventurous caves, gorgeous forests, and hidden hot springs (Umpqua Hot Springs). 
• The Willamette Valley: Known for its amazing wine, tulips, and orchards, this farming community is a hub for a perfect weekend getaway.

Great…So Where Do I Start My Oregon Road Trip?

The easiest place to start your Oregon road trip is in Portland . This is the biggest city, where you will find the most options for car rentals, flights into the state ( Portland International Airport – PDX ), and stores to pick up any last-minute supplies.

Our Oregon road trip itinerary has you starting in Portland and heading east, but you can always fit the route to suit your own needs and desires! Keep scrolling to see all the stops so you can make your decision.

How Do I Get Around On My Oregon Road Trip?

The easiest way to get around on an Oregon trip is to drive in a car . It’s unreasonable to believe that you can fly from place to place. The biggest major airport is in Portland (PDX) and the rest are smaller local airports.

It’s easiest to get around Oregon in a car , and we highly suggest this mode of transportation! If you are hoping to do some camping along the way, we recommend checking out the company Outdoorsy to rent a campervan . It’s like having your transportation AND accommodations all in one place.

Outdoorsy does local recreational vehicle rentals (kind of like Airbnb but for cars!) so you can travel around Oregon in style with a cool vintage VW bus or cute teardrop trailer!

Where Do I Stay During My Oregon Road Trip?

The good thing about Oregon road trips is that they are completely customizable! You can stay at some of the coolest lodges and hotels in Oregon, explore backcountry roads for camping, or do a little mix of both!

Finding Epic Campsites in Oregon: There are so many amazing campsites in Oregon that the topic requires its own blog post! However, one of our most coveted tools for finding the best camping spots is through The Dyrt . The Dyrt is a campground finding app , and one of the best ones we’ve used! It’s got great reviews with photos, offline maps, road trip routing tools, and more! Our readers get to try it free for 30-days by using our code Mandagies !

Our favorite lodges & resorts in Oregon: Some amazing accommodations stand out among the others, and we think that some of these places deserve their own recognition! Here are some of our favorite lodges in Oregon that we recommend checking out!

FivePine Lodge – Sisters, OR (Central) Bay Point Landing – Coos Bay, OR (Southern Coast) Headlands Lodge – Pacific City, OR (Northern Coast) The Independence Hotel – Willamette Valley (Northwest/Central Oregon) Looking for vacation homes? Browse our favorite cabins on the Oregon Coast !

The Mega Oregon Road Trip Itinerary (All The Best Stop In Oregon)

This two week Oregon road trip will bring you to all the best spots!

Stop 1: Portland, Oregon

Before departing the city, spend some time visiting Portland’s coolest locations! Some of the most popular outdoor places to visit in the city include the Portland Rose Garden, Washington Park, the Pittock Mansion (with its view of the city!), and Forest Park.

Grab a bite to eat at one of the several food truck communities around town. Click here to locate all the food truck pods around Portland!

From here, make sure to stock up with snacks at your favorite grocery store, fill up with gas, and hit the road!

Stop 2: Columbia River Gorge Scenic Byway

Begin your Oregon road trip in Portland and head to Interstate 84 East to start your Columbia River Gorge Scenic Drive . This is a great start to any Oregon road trip itinerary for its iconic stops like Multnomah Falls, Latourell Falls, and Bridal Veil Falls. 

If you want to go hiking in the Gorge , consider Wahclella Falls Trail (only 1.9-miles long) or Munra Point Trail for incredible panoramic views.

To spend more time checking out cool waterfalls in Oregon , consider taking the Historic Columbia River Highway (that parallels I-84), which provides easy access to many of them. Don’t forget to drive a little farther than Hood River to check out Rowena Crest , that famous hairpin road!

Note: The Eagle Creek Fire of 2017 devastated much of this area, and hikes/waterfall trails are slowly opening after restoration efforts. Click here to be updated on real-time trail openings in the Columbia River Gorge . 

Extra Stops Between Portland and Hood River:

• Vista House – A museum, observatory, and rest stop
• Bridge of the Gods – Many of the Pacific Crest Trail Hikers cross here!
• Beacon Rock State Park (on the Washington side)
• More than 25 Columbia River Gorge waterfalls to see!

Stop 3: Hood River, Oregon

Hood River, Oregon is the perfect place to stay after a day of planning fun things to do in the Columbia River Gorge ! Placed conveniently on the river’s edge, there is easy access to Mount Hood directly south, water activities like windsurfing , and Washington waterfalls right across the river in the Gifford-Pinchot National Forest to the north.

If you want a little more adventure, consider crossing the toll bridge ($2) to Washington and venturing on nearby trails to Falls Creek Falls , Panther Creek Falls, or Lower Lewis Falls.

Cool Places To Stay in Hood River, Oregon

Modern Townhome in White Salmon, WA (just across the river) MtAdamsView in Hood River (TONS of gorge and mountain views, sleeps 6) Best Western Plus in Hood River (great value, free breakfast)

Stop 4: Mount Hood

Route your Oregon road trip from the river’s edge to the mountains, more specifically to all the cool things to do in Mount Hood !

Watch a sunrise at  Trillium Lake – one of the easiest lakes to reach on Mount Hood. On a clear day, you will be able to see the reflection of the picturesque Mount Hood beautifully framed in the distance! Other Mount Hood lakes include Frog Lake,  Lost Lake,  and  Mirror Lake –  each with their own unique reflection of the mountain. 

If you are interested in discovering some cool hiking trails around Mout Hood, consider  Ramona Falls trail. This gorgeous horsetail falls is hidden deep in the forest, but the payoff is huge once you see it with your own eyes. Care for a short waterfall hike for your Portland day trip? Consider  Tamanawas Falls , an easy 3.3-mile trail with a gorgeous view!

Want to challenge yourself? Here are some other longer hikes in the Mount Hood area.

• Tom Dick and Harry  (9 miles out and back)
• Bald Mountain  (6 miles out and back)
• McNeil Point Trail  (9.6 miles out and back)

Stop 5: The Painted Hills

After stopping at Mount Hood (overnight or just for a day trip) take the 3.5-hour drive from Mount Hood to the Painted Hills to catch a gorgeous sunset in the Oregon desert. 

The Painted Hills gets its name from the exposed layers of colorful soil that are revealed in the rolling hills of the John Day Fossil Beds . Make sure to stay on the boardwalks as you explore the Painted Hills. The hills are extremely fragile!

In the morning, return to the John Day Fossil Bed units and see the Painted Hills as the sun rises! This is a gorgeous time of day in the hills, and you’ll likely get it all to yourself in the early hours of the morning. 

Need a place to sleep? Consider these nearby campgrounds (or click here to discover FREE campsites nearby too! )

Stop 6: Smith Rock State Park

From the Painted Hills through the Ochoco National Forest , take the 1.5-hour drive to Smith Rock State Park . Smith Rock is a hub for climbers , but there are several other things to do here, including hiking, biking, and taking photos!

To stretch your legs on this Oregon road trip, take the short but *very* steep Misery Ridge Trail . This 0.68-mile trail climbs 600 feet giving even the most experienced hiker a run for their money! The views at the top are worth it though, especially during sunrise or sunset!

Stop 7: Bend, Oregon

The city of Bend is an excellent stop on any good Oregon road trip! It’s an outdoor-loving town that connects Western Oregon and Eastern Oregon, making it a great pit stop to pick up last-minute gear, groceries, and maybe even tune ups for your car.

For a little relaxation from the road, grab a beer in town at any of the iconic stops on the Bend Ale Trail . If you are visiting in the summertime, floating the Deschutes River is a popular activity on a hot day. Make sure to bring your PFDs, water sandals, and a garbage bag!

In the morning, grab breakfast in Bend at The Sparrow Bakery, (their ocean rolls are famous!), and some to-go coffee at Spoken Moto and make some fun stops around Bend on your way south. Lava Island Falls and Lava River Cave are both easy and accessible places to see along your Oregon road trip route going out of town.

More adventures near Bend, Oregon

• Hiking to Tumalo Falls (6.5 miles out-and-back)
• Go backpacking in the Three Sisters Wilderness
• Take a road trip detour on the Cascades Lake Highway

Read More: How to Spend 4 Days In Bend, Oregon

Oregon Road Trip Bonus Route – Eastern Oregon!

Psst…want to spend a lot more time in Eastern Oregon? Check out our Eastern Oregon Road Trip route right here !

From Bend, you have the option of extending your Oregon Road trip going east , or continue south and west towards the coast! Either option is great, it really just depends on how much time you have.

Stop 8: Oregon Waterfalls

The drive from Bend to Crater Lake National Park is pretty short, about 1.5 hours. This gives you plenty of time to make some fun stops along the way , most notably, to waterfalls in Oregon !

For longer Oregon waterfall hikes, make your way west on Highway 58 for a fun hike at Salt Creek Falls and Diamond Creek Falls . Continue your drive south and divert north on Highway 138 for a stop at Watson Falls before making your way to the Crater Lake North Entrance. 

More Oregon Waterfalls Near The Area:

• Proxy Falls (Highway 242 – North of Bend)
• Chush Falls (Near Sisters, Oregon)
• Dillon Falls
• Benham Falls

Stop 9: Crater Lake National Park

Crater Lake National Park is one of the most iconic stops on an Oregon road trip, and the ONLY national park stop in the state. Spend sunset capturing the iconic Wizard Island on Crater Lake, and top it off by spending the night at the historic Crater Lake Lodge .

In the morning, spend an entire day hiking around Crater Lake on Watchman Peak Trail, Cleetwood Cove Trail, or Cloudcap Overlook.

At Crater Lake , you can spend the morning driving the Rim Drive , which takes about 2 hours to go all the way around. Hike to Plaikni Falls in the afternoon and in the evening watch the sunset at Garfield Peak or Sinnott Memorial Observation Station.

Bonus Oregon Road Trip Stop: Oregon Hot Springs

Now, this is the part of your road trip route in Oregon where you can choose where you’d like to spend your time! You can opt to continue driving east to explore some of the famous Eastern Oregon hot springs . 

If you decided to check out some hot springs in Oregon , we highly suggest booking an overnight stay (Summer Lakes Hot Springs and Crystal Crane have lodging available!) or bringing your camping gear to find some free camping nearby . 

Here are some Oregon hot springs you should be checking out on this leg of your Oregon road trip itinerary:

• Crystal Crane Hot Springs – Hot spring pond and private soaking tubs
• Summer Lakes Hot Springs – Communal bathhouse
• Hart Mountain Hot Springs – Structured underground pool and open springs, both natural
• Have an extra day? Drive farther east and check out Alvord Hot Springs , and Willow Creek Hot Springs !

Stop 10: Umpqua National Forest

Another iconic destination on your Oregon road trip is an adventure in Umpqua National Forest . You’ve probably seen pictures of those cliffside hot springs pools, or the rushing waterfall flanked by towering basalt cliffs. Well, these places are Umpqua Hot Springs and Toketee Falls !

Both places are easy to reach, each with a short hike to the final destination. Come with a national forest pass to hang in your car’s rearview mirror. You can pick one up at the Diamond Lake Ranger Station nearby if you need one. See the difference between Pacific Northwest forest passes here to find the correct one.

Leave No Trace Notes: Umpqua Hot Springs is notorious for garbage . Please pack out your trash, and consider taking other garbage with you, too. Hiking to the base of Toketee Falls is prohibited , no matter how many pictures you see of people doing so. It is possible to get cited for climbing down to the bottom, so don’t risk it!

Stop 11: Southern Oregon Coast

Finally, the first ocean stop on your Oregon road trip!

The Southern Oregon Coast is arguably the most beautiful area of an Oregon road trip. If you love seaside cliffs, hidden coves, and gorgeous beaches, this is the place for you!

Spend some time exploring the 12 miles of protected coastline at Samuel H. Boardman Scenic Corridor . This part of your road trip in Oregon will take an entire day, between stops, viewpoints, and even a hike to a place called Secret Beach .

Finally, end your day in Gold Beach for the evening. Here, you can find tons of amenities, hotels, and beach rentals for a quiet and relaxing evening. Make sure to stop at our favorite beach, Myers Creek Beach to enjoy a beautiful Oregon coast picnic to end the day!

Read More: The 25 best beaches in Oregon (From North to South!)

Stop 12: Central Oregon Coast

Central Oregon is full of adventurous destinations and unique curiosities. If you like thrills, try renting an ATV to ride across the Oregon Dunes, stretching 40 miles across the coastline.

You can also check out incredible places like Cape Perpetua , which is filled with churning coves, sea spouts, and lots of tide pools along the Oregon Coast .

Devil’s Punchbowl State Natural Area is another great place to explore, with a giant sea cave and surfing opportunities!

In the evening, splurge to go glamping and one of Coos Bay’s coolest spots – Bay Point Landing ! This luxury camping resort has plenty of pull-in sites for RVs and trailers. You can also rent a standalone cabin , airstream , or renovated RV of your own to enjoy upscale camping. The grounds have amenities like a pool, lounge room, upscale bathrooms, and a cute camp store.

Stop 13: Eugene, Oregon

If you wanted to go inland to explore the Cascade Mountains, this is the part of your Oregon road trip to make that decision! Drive away from the Oregon coast to go inland to Eugene, Oregon, and explore this upbeat college town.

But before leaving the coast, consider stopping by Heceta Head Lighthouse and Cape Perpetua for one last adventure by the water. The lighthouse can be seen up close with a short hike, which is incredible at sunrise and sunset!

Cape Perpetua is best explored during low tide, where you can access the many tide pools and curiosities that dot the shore. If you do come during high tide, don’t fret! You can see the waves push up through Thor’s Well for a dramatic display, and the Devil’s Churn to watch the waves crash around this small cove. 

Stop 14: Willamette National Forest

Heading inland from Eugene, there are a ton of beautiful places to see in the Willamette National Forest . The first stop is Terwilliger Hot Springs (often called Cougar Hot Springs) for a lovely natural soak. Keep driving to choose a waterfall adventure – Proxy Falls , Sahalie and Koosah Falls , The Blue Pool , and Tamolitch Falls .

You’ll want to spend at least a full day in this area (or even go camping overnight!) because the trails here are packed with adventure! Keep driving on Highway 126 as it continues on Highway 22 north to Silver Falls State Park and Salem, Oregon to continue on your epic Oregon road trip.

Stop 15: Salem and The Willamette Valley

If you like good food, you’re going to love this stop on your Oregon road trip. The Willamette Valley is full of wineries, farms, and beautiful vineyards! There are lots of options to enjoy farm-to-table dinners, wine tastings, and all-day experiences. Consider staying nearby at the Independence Hotel .

For a little adventure, head to Silver Falls State Park where you can hike the Trail of Ten Falls . This Oregon hike is exactly what its name entails – ten beautiful falls in an 8.7-mile trail. Come enjoy this condensed version of many iconic Oregon waterfalls all in one place!

Stop 16: Northern Oregon Coast

Refueling in Salem, it’s time to get back to the coast! The final stops on your Oregon road trip include classic North Oregon Coast stops and beautiful Oregon beach towns , hikes, and plenty of dreamy overlooks.

Beginning in Cape Kiwanda , spend the day hiking up the sand dunes to watch the dory boats dock onshore and paragliders sail down to the beach. Make sure to stop and eat lunch at Pelican Brewing . They have incredible beer and pub food, with an outdoor patio overlooking Pacific City’s own Haystack Rock.

Continuing north to another iconic “Haystack Rock” (arguably the most popular one too) Cannon Beach is the best place to grab a coffee and take a walk along the beach. During low tide, you can get close to the rock and spot puffins in their natural habitat!

If you want a little more adventure in your day, drive up to Ecola State Park to hike Crescent Beach Trail , the trail to Indian Sands, or Tillamook Rock Lighthouse Viewpoint. These lush Oregon Coast hikes are sure to leave you breathless!

Stay either at the Headlands Lodge in Pacific City , Oregon Coast Modern Cabin in Manzanita , or affordable hotels in Cannon Beach !

Stop 17: Finish Your Oregon Road Trip Back to Portland, Oregon 

On your way back to Portland to finish your Oregon road trip, you can take the short way on Highway 26, or the long way through Astoria, Oregon, and heading back to the city on Highway 30.

The detour through Astoria won’t disappoint! Filled with great restaurants, antique and vintage shops, and lots of history, it’s a perfect final stop on the Oregon coast road trip section of your drive.

For outdoorsy activities, stop by Fort Steven’s State Park to check out the historic military installation, as well as the famous Peter Iredale shipwreck . For hiking, stay close to town and check out the Cathedral Tree Trail and the Astoria Column .

And you’ve done it! You’ve completed the coolest Oregon road trip to see all the best highlights, hikes, and iconic locations in the state.

Oregon Road Trip Itinerary Examples

Below, we’re sharing some Oregon road trip itinerary examples to help you customize it exactly to fit your needs. For even more resources, we created this road trip itinerary in Oregon to print out and take on your journey!

(We’re running some email maintenance – this download will be back soon!)

Two Week Oregon Road Trip

See the detailed breakdown of our two-week Oregon road trip itinerary above!

10 Day Oregon Road Trip

You can see a lot with 10 days in Oregon! This route is a compressed version of our two-week road trip, with just a little less time in each spot but plenty of stops for an epic and interesting route!

• Day 1: Portland to Hood River
• Day 2: Hood River to Bend, Oregon
• Day 3: Bend, Oregon to Crater Lake National Park
• Day 4: Crater Lake to Umpqua National Forest
• Day 5: Umpqua National Forest to Samuel H. Boardman
• Day 6: Samuel H. Boardman to Coos Bay
• Day 7: Coos Bay to Eugene, Oregon
• Day 8: Eugene, Oregon to Salem, Oregon
• Day 9: Salem, Oregon to Cannon Beach
• Day 10: Cannon Beach to Portland, Oregon

One Week Oregon Road Trip

One week for an Oregon road trip will introduce you to Oregon’s vast and diverse landscape! From Crater Lake to Bend, Coos Bay to Cannon Beach, this route will bring you to some of the best of Oregon photography locations. 

• Day 1: Portland to Hood River
• Day 2: Hood River to Bend, Oregon
• Day 3: Bend, Oregon to Crater Lake National Park
• Day 4: Crater Lake to Samuel H. Boardman
• Day 5: Samuel H. Boardman to Coos Bay
• Day 6: Coos Bay to Cannon Beach
• Day 7: Cannon Beach to Portland, OR

5 Day Oregon Road Trip

With 5 days in Oregon, you can see the highlights! This quick trip averages about 3-4 hours of driving per day, and takes you through mountains, by waterfalls, and meets up with some of the most scenic views along the Oregon Coast.

• Day 1: Portland to Bend
• Day 2: Bend to Eugene
• Day 3: Eugene to Samuel H. Boardman
• Day 4: Samuel H. Boardman to Yachats
• Day 5: Yachats to Portland

Have you ever experienced an Oregon road trip? What Oregon itinerary is your favorite? Tell us in the comments below!

Amazing! I know nothing about traveling all over the country, what a wonderful looking place to explore.

I’m really glad you liked our Oregon road trip route! I hope you et a change to travel across this beautiful state!

Your Ultimate Oregon Road Trip—1 Week to 1 Month Oregon Itinerary

We can’t lie, writing up this ultimate itinerary for an Oregon road trip was HARD.

We couldn’t stop, we kept writing and writing, and next thing you know, we came out with this monster Oregon itinerary that could last you around a MONTH. Yes, an entire month around Oregon.

As epic as that would be, we know that not everyone has 30 days to traverse our massive, stunning, and truly adventurous state .

With that said, we weren’t going to deprive you of choices! So, welcome, this just may one of the longest and craziest posts on road-tripping Oregon out there.

Don’t get intimidated; we laid everything out very easily for you to pick and choose and personally curate your own legendary Oregon road trip.

Fill up your gas, grab your supplies, and head on out!

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Table of Contents

Your Ultimate Oregon Road Trip Itinerary

Ecola state park – 1 day, arch cape – 1 day, cape meares – 1 day, sand lake recreational area – 1 day, lincoln city –  1 day, depoe bay – 1 day, yaquina head – 1 day, cape perpetua – 1 day, sea lion caves – 1 day, shore acres state park – 1 day, samuel h. boardman state scenic corridor – 1 day, where to stay on the oregon coast, mount hood – 2 days, silver falls state park – 1 day, columbia river gorge – 1 day, where to stay near portland, deschutes river – 1 day, umpqua national forest – 1 day, smith rock state park – 1 day, cascade lakes scenic byway – 1 day, three sisters wilderness – 1-2 days, newberry crater national volcanic monument – 1 day, crater lake – 1 day, where to stay in central oregon, wallowa mountains – 2 days, sumpter – 1 day, mitchell – 1-2 days, strawberry mountains – 1 day, umatilla national forest – 1 day, owyhee canyonlands – 1-2 days, steens mountain – 1-2 days, hart mountain – 1 day, summer lake – 1 day, where to stay in eastern oregon, an oregon road trip itinerary, tips for your oregon road trip, a legendary oregon coast road trip—35 stops & 3 itineraries, 29 awesome things to do on an eastern oregon road trip, 19+ adventurous things to do on a washington road trip, 21+ adventurous things to do on a northern california road trip, 25 day trips from portland, oregon + road trip ideas.

For the sake of ease, we’ve sliced up Oregon into four sections. The Coast , Central , Near Portland , and then East Oregon .

We know this split isn’t an accurate representation of how Oregon is divided, but we think a good chunk of people reading this may not be from Oregon and, therefore, can digest the vastness of the state a bit easier this way.

Of course, as per usual, we also offer you a handy little map because visuals are ALWAYS better when planning out a road trip, always.

Below you’re going to read about some of our favorite highlights from each section of Oregon, and each section will need at least a week to ride through and experience. You may not be able to hit up every highlight we have here, but we had to give you some choices.

We’ve also included the number of days next to each spot. Do note, this is the absolutely MINIMUM amount of time you’d need. Most will state one or two days, and we mean an entire day or two.

This will just give you a taste of the area, or if it’s small enough, a single day may really be all you need.

Also note this is not included driving. Again, it’s a full day of exploring, hiking, rock climbing, out on the lake with your sport of choice, etc… Please add in driving days as needed.

As we like to mention here often, particularly from visitors to the USA, our country is freakin huge, dudes! Like, mega massive. So please plan accordingly.

Driving around the USA, and yes, that means Oregon too, requires more time than you think. Always add on an hour or so to the estimation Google Maps gives you to be safe.

We’ve also added in tons of additional links through this post which give you a deeper dive into a lot of the places and areas mentioned here so click those for more info.

Anyway, get your travel pants on, snacks stocked, and let’s get this Oregon road trip rolling! Right?

✋ HOLD UP! Don’t Forget…

You need some wheels! It’s nearly impossible to get around the USA and check out the best adventures without a car! Here are our top recommendations…

🚗 Rent a car

If you don’t have your own, renting a car is your best bet!

👉 Find Deals on Cars and SUVs

🚐 Rent a home on wheels

For the more adventurous, rent a van or RV and ditch the hotel.

👉 Find The Best Van For Your Trip

Don’t Forget This!

A lot of the best adventures around Oregon will require a Northwest Pass. You can easily get one delivered straight to your door. Grab it now before you leave !

Oregon Coast Road Trip Itinerary

The rugged Oregon coastline is one of those places that feels like you’re living in a dream. Stretching for over 360-miles against the wild Pacific Ocean, the Oregon Coast is loaded with awe-inspiring natural scenery and vibrant communities.

From its serene beaches to towering sea stacks, each section of the coast will keep you on the edge of your seat during your Oregon road trip.

Sandy beaches, craggy cliffs, scenic viewpoints, lush forests, alluring tide pools, shipwrecks, rolling sand dunes, and monstrous waves are all accessible just off the highway. What more could you want for a life-changing Oregon itinerary?

Have your camera ready and explore the picturesque coastline that has captured the hearts of Oregon lovers everywhere!

• Explore the never-ending hiking trails through its tranquil forests like the Clatsop Loop and Crescent trails.
• Capture a breathtaking panorama at one of Oregon’s most famous viewpoints. From atop the cliffside, you have the perfect angle of towering rock formations rising out of the ocean.
• Head to Indian Beach to spot tide pools and have a relaxing picnic while you listen to the waves crash against the shore.

READ MORE: Your Guide to Ecola State Park on the Oregon Coast

• Experience blissful solitude while feeling the sand between your toes on this pristine shoreline.
• Explore the enchanting caves, gorgeous waterfall and shallow tide pools of Hug Point State Park .
• Get a brilliant bird’s eye view of the Pacific Ocean, long stretches of the coastline and the coastal town of Manzanita at the Neahkahnie Viewpoint.

• Add a detour along the Three Capes Scenic Route to your Oregon itinerary for a sensational drive down the Tillamook coastline. The journey takes you to Cape Lookout and Cape Kiwanda for miraculous views of verdant forests and sand dunes.
• Go bird watching to see colonies of nesting murres and other beautiful avian species.
• Wander inside the Cape Meares Lighthouse for a thrilling view on the cliffside roughly 200-feet above the ocean.

RELATED: Three Capes Scenic Route on the Oregon Coast

• Go off-roading through sand dunes in between the crashing waves of the Pacific and a coniferous forest.
• Spend the night camping at this enormous lake of sand and witness a dreamy sunrise against the ocean.
• Spend the night at one of the most scenic Oregon coast towns by camping at Devil’s Lake near downtown Lincoln City . The lake offers a wide range of outdoor activities such as fishing, kayaking, and hiking.
• Enjoy a day on the water at Siletz Bay by kayaking, boating or fishing on its tranquil shores.
• Hike the God’s Thumb via the Knoll, one of the most breathtaking Oregon Coast hikes . The end of the trail features a peculiar basalt formation shaped like a thumb offering sensational views of the coastline.
• Check out the interesting statue of Abraham Lincoln and waltz through the town’s Historical Museum.

READ MORE: Your Guide to the God’s Thumb Hike Near Lincoln City

• Stop by the Whale Watching Capital of the Oregon Coast during this Oregon road trip to search for majestic gray whales.
• Just south of the whale hotspot, you’ll find the roaring power of the Devil’s Punchbowl. This enormous bowl was created by collapsed sea caves and gives you a glimpse of the ocean’s power with its ferocious waves.

• Tour the Yaquina Head Lighthouse, the tallest and most historic lighthouse in Oregon. Tickets to the lighthouse are on a limited basis but the panoramic views of the structure perched along the scenic bluffs are some of the best on the entire Oregon coast.
• Hike the rocky shoreline beneath the lighthouse to spot whales, seals, eagles and beguiling tide pools.
• Drive to the highest Oregon coast viewpoint accessible by car and stand in awe of the hair-raising vista overlooking the horizon. You’ll be standing 800-feet above the crashing waves of the Pacific Ocean and this stop on your Oregon itinerary will make your heart skip a beat.
• Marvel at the geologic formations of Thor’s Well and Devil’s Churn. Thor’s Well is a seemingly bottomless pit sucking waves into its grasp and Devil’s Churn will overwhelm you with the force of tenacious waves pounding a rocky inlet.

RELATED: 9 Things to Do in Cape Perpetua, Oregon

• Ride the elevator to the depths of the largest sea caves in the United States. Keep in mind that this includes a fee of $14.
• Spot adorable sea lions lounging inside the massive cave system. If your Oregon road trip is during the winter, then there is a great chance you’ll see hundreds of these amazing creatures.
• Head to the nearby Heceta Head Lighthouse for a remarkable view standing atop a rocky cliff.
• Stand at the park’s scenic viewpoint and witness thunderous waves pounding the jagged rock formations on the coastline.
• Wander the grounds of a former mansion to smell the radiant flora of rose gardens and a Japanese-style garden.
• Walk along the shores of Simpson Beach and relax at its isolated cove.

• Explore the miles of beautiful coastal trails the Samuel H. Boardman State Scenic Corridor has to offer. The Lone Ranch South Trail is an easy trek offering breathtaking seaside vistas and the Whales Head Beach Trail meanders to one of the most peaceful beaches in the corridor.
• Hike to the Natural Bridges for spectacular views of geologic structures and spruce-tree forests.
• Enjoy the serenity of Secret Beach and gaze at the towering rock formations nestled along the shore.
• Before continuing your Oregon road trip, peek through the forest and watch a gorgeous sunset at Arch Rock.

Southern Oregon Coast: 13 Epic Stops—Bandon to Brookings!

17 Breathtaking Oregon Coast Hikes

11 Most Scenic Oregon Coast Towns (And What to Do There!)

17 Cool Oregon Coast Camping Spots To Stay At

→ If you don’t have a lot of time, do this Oregon Coast day trip from Portland to see the best of the coast with a local.

Recommended Places:

• Adorable Seaside Cottage
• Happy Camp Beachfront Cabin
• Captain’s Quarters

Campgrounds: Wright’s for Camping | Devil’s Lake State Recreation Area | Harris Beach State Recreation Area Campground

Near Portland, Oregon Road Trip Itinerary

We love Portland , naturally. But we love the places on the outside of Portland way more.

Cascading waterfalls galore, a cornucopia of excellent hikes, and the majestic Mount Hood just on the outskirts of the city make Portland a playground for Oregon adventurers.

After you’re done stuffing your face with Voodoo donuts and taking the iconic “Portland is weird” sign selfie, then get out and do something in nature!

The furthest you’ll drive from Portland to anything in this section is only about two hours one way. You’ll be gobsmacked by the things to do just outside the concrete jungle of Portland.

• Enjoy spectacular views of Oregon’s tallest mountain from all angles by embarking on many awesome Mount Hood hikes . Some of the best hikes include the Tom Dick and Harry Trail and Mirror Lake Loop , Lost Lake, Tamanawas Falls , and the Trillium Lake Loop and they all give you glorious vistas of Oregon’s most famous peak.
• Summit the craggy pinnacle and have the exhilarating feeling of standing on the roof of Oregon.
• If you have a snow-filled Oregon itinerary, experience Mount Hood in winter by skiing or snowboarding down its slopes. Just be aware of possible road closures in the area around the mountain during winter.

→ If you don’t have a lot of time, do this Mount Hood Day Trip from Portland to see the best of the area.

• Hike the Trail of Ten Falls to experience one of the most beautiful hikes near Portland. The 7.6-mile loop passes ten alluring waterfalls and is considered one of Oregon’s natural wonders.
• Hit the park’s backcountry trails for mountain biking and horseback riding adventures.
• Spend the night at the campground and listen to the soothing sounds of the waterfalls before continuing your Oregon road trip.
• Capture the perfect snapshot of Oregon’s most famous waterfall in all her glory—Multnomah Falls
• Discover more cascading waterfalls in the Columbia River Gorge by hiking the Wahkeena-Multnomah Loop. This invigorating trek takes you through lush vegetation, volcanic cliffs and far away from the crowds.

17 of the Best Places for Camping Near Portland

19+ Awesome Hikes Near Portland to Escape the Bustle

What to Do At Mount Hood in Winter

A Guide to The Columbia River Gorge

→ If you don’t have a lot of time, do this highly rated half-day tour from Portland to see the best waterfalls in the Columbia River Gorge.

• Tiny House With Lofted Views of the Forest
• Peaceful Garden Cottage
• Tiny Forest Cabin

Campgrounds: Beaver Campground | The Vintages Trailer Resort | Oxbow Regional Park 

Central Oregon Road Trip Itinerary

When it comes to jaw-dropping natural scenery, it’s impossible to replicate the magic that central Oregon presents. There’s a reason why many of the state’s most iconic sights are in this dynamic region.

From the majestic Cascade peaks to the tumbling waterfalls of the Columbia River Gorge , Central Oregon has it all.

This portion of your Oregon road trip transports you to several of the state’s tallest mountains, evergreen forests, crystalline lakes, and mysterious craters. The biggest challenge will be narrowing down your Oregon itinerary to fit your schedule.

Central Oregon’s diversity is simply unmatched and traveling down its scenic byways will show off its splendor at every turn.

If you’re looking to experience Oregon at its absolute finest, central Oregon has got you covered!

• Climb into a raft and float down the Deschutes River for an afternoon of total relaxation.
• Enjoy more exciting activities by the river like kayaking, fishing or even take a crack at surfing .
• Hike the Deschutes River South Canyon Trail or the Deschutes River Trail Loop for a delightful stroll by the river.

• Camp in the tranquil forest and hike through pine trees, wildflowers and dense vegetation to reach many mesmerizing waterfalls. The Toketee Falls Trail, Watson Falls Trail and Lemolo Falls Trail are among the scenic paths in Umpqua National Forest .
• Venture down the Twin Lakes Trail for sensational views of dazzling lakes and find the perfect spot for a picnic.
• Soak in the terraced pools of the Umpqua Hot Springs and watch the peaceful flow of the Umpqua River.
• Kayak on the shimmering waters of Diamond Lake as the ‘lightning rod’ Mount Thielsen towers above you. For an action-packed expedition to include on your Oregon road trip, get your adrenaline pumping on the Mount Thielsen hike to reach the summit of the jagged peak.

• Hike along the Crooked River and gaze at the craggy pinnacles rising high into the sky.
• Test your endurance by climbing Misery Ridge and watch rock climbers test their wits at the oddly shaped Monkey Face.
• Learn how to rock climb yourself since this stop on your Oregon itinerary is the premier location in the state for the sport.
• Marvel at golden eagles, rattlesnakes, otters and other beautiful wildlife that call these sharp canyons home.

• Visit the sparkling lakes decorating this famous driving route such as Todd Lake, Sparks Lake and Elk Lake . This 66-mile highway takes you from the vibrant city of Bend to some of the most popular getaways in central Oregon.
• Stand in awe of the snow-capped Cascade peaks overlooking the alpine lakes lining the byway. Mount Bachelor , Broken Top Mountain and South Sister are a few of the iconic mountaintops in perfect sight.
• Enjoy an abundance of outdoor activities by the lakes such as fishing, hiking, mountain biking and paddling.
• You have countless camping options to include in your Oregon road trip for an extended stay near the byway.

• Gear up for one of the ultimate challenges on this Oregon road trip by tackling the South Sister Trail . This 12.2-mile trek takes you to the peak of Oregon’s third-highest mountain and rewards you with jaw-dropping vistas of the nearby peaks.
• Take on another daring expedition by trekking the Broken Top Trail to No Name Lake and Bend Glacier. This thrilling hike will take you through subalpine forest and provide a close encounter with Broken Top’s serrated pinnacles.
• If you have time, hike part of the Three Sisters Loop to marvel at the area’s volcanic landscapes.

RELATED: Your Guide to Hiking South Sister in Bend, Oregon

• Admire the otherworldly geologic landscapes and the remnants of powerful volcanic blasts from thousands of years ago at Newberry National Volcanic Monument .
• Hop on your mountain bike and ride around the Newberry caldera using the rim trail.
• Hike the Paulina Peak Trail to experience one of the best Oregon hikes and possibly the most awe-inspiring vista in central Oregon. The views here give you 360-degree views of Paulina Lake, the Big Obsidian Flow and other peaks of the Oregon Cascades.

READ MORE: Your Guide to Newberry National Volcanic Monument

• Include the Rim Drive on your Oregon road trip to conquer the 33-mile loop that circles the caldera rim.
• Hike the Garfield Peak Trail for incredible scenery overlooking the deep-blue hues of the lake and the surrounding Cascade peaks. You’ll have a spectacular view of Phantom Ship, Wizard Island, and other beautiful landmarks.
• Head to Cleetwood Cove for an interesting vantage of the lake from inside the caldera.

A Guide to Smith Rock State Park’s Hikes, Misery Ridge Trail & More

• An Adventurer’s Guide to Things to Do in Bend, Oregon

The Tamolitch Blue Pool Hike + Sahalie and Koosah Falls

• Cozy Sunriver Cabin
• Hummingbird Cottage
• Tall Pines A-Frame

Campgrounds: Elk Lake Campground | Jasper Point Campground | Redmond/Central Oregon KOA

Eastern Oregon Road Trip Itinerary

Very few people are in the loop of the majestic scenery decorating the eastern half of Oregon. And it’s a shame that this section of the state doesn’t receive the same hype as its coast and Cascade brethren.

Sparkling lakes, snow-capped mountaintops, mesmerizing deserts, craggy gorges, verdant forests, striking canyons, rejuvenating hot springs and some of the best stargazing on the planet.

With this much jaw-dropping natural beauty, it’s hard to fathom that this is the least discovered region of Oregon. Maybe it’s best to keep it that way to preserve this wild canvas of untouched terrain.

It may sound cliché to wander off the beaten path, but that is exactly the type of adventure eastern Oregon provides on your Oregon road trip.

• Explore the rugged terrain of the Wallowa Lake State Park by trekking the Hurricane Creek Trail or para-glide above the park for a once-in-a-lifetime experience.
• Swim in the pristine waters of Wallowa Lake surrounded by dense forests and rugged peaks. Its crystalline waters are a beautiful spot for snorkeling, or you can sunbathe on the sandy shores for a tan.
• Ride the Wallowa Lake Tramway for unbelievable mountain vistas.
• Trek the Mirror Lake to Eagle Cap Trail to reach the summit of Eagle Cap. Enjoy the sensational views of alpine lakes, beautiful forests and glaciated valleys.
• Grab your paddle and steer around jagged boulders in the exhilarating class III and IV rapids of Eagle Creek.

• Dress up like Wild West characters at the charming Sumpter Stockade Motel.
• Learn about Oregon’s rich gold mining history with a visit to the Sumpter Valley Dredge .
• Spend an exhilarating day riding around on an ATV before hopping back on the highway.

→ While in Sumpter, head to nearby Baker City to do some stargazing and wine tasting on this fantastic tour .

• Hike through the Ochoco National Forest for remarkable images of lush forests, bewildering geologic formations and vibrant wildlife. Its tranquil waterways are the perfect outlet for a fishing or boating excursion.
• Discover the otherworldly beauty of the Painted Hills , one of Oregon’s greatest natural treasures. The layered bands of yellow, red, orange and gold make the perfect stop on your Oregon itinerary to marvel at the state’s alien-like landscapes.
• Explore the hiking trails less-visited around the John Day Fossil Beds area to study Oregon’s ancient history. Sheep Rock and the Clarno Unit are both a must for geology lovers.

• Unleash your adventurous spirit by hiking through the less-traveled Strawberry Mountain Wilderness. This nature lover’s playground is teeming with alpine lakes, sharp peaks, blooming wildflowers and an abundance of wildlife.
• Reach the peak of Strawberry Mountain for one of the most liberating summits on your Oregon road trip. The heart-racing vistas hear make you feel like you’re on top of the world.
• Unwind in the great outdoors at the crystal clear waters of Strawberry Lake. This is an ideal camping spot for your Oregon itinerary with its lush forests, rugged mountains and quality fishing.

• Spend the night at Jubilee Lake Campground for another beautiful night underneath the stars during your Oregon road trip. Jubilee Lake is a peaceful hideout deep in the forest and a wonderful spot to escape the scorching temperatures of summer.
• Enjoy a tranquil ride down the class II rapids of the Grande Ronde River and gaze at the steep canyons rising above you.
• Watch for deer, bighorn sheep, eagles and other wildlife (including rattlers) on the roughly 30-mile Wenaha River Trail. The meandering river, towering cliffs and tranquil forests make this a fantastic backcountry adventure to add to your Oregon itinerary.
• Experience one of Oregon’s most exciting whitewater rafting excursions on the Owyhee River. The class III and IV rapids snake between basalt columns and red-rock cliffs creating an unbelievable ride.
• Explore some of Oregon’s most isolated hiking trails through the Owyhee Canyons and marvel at the sheer-canyon walls soaring above you.
• Make the Owyhee Canyonlands another one of your camping sites on your Oregon itinerary for a stellar night of stargazing.

• Push your adrenaline to the max by driving the 60-mile Steens Mountain Loop, one of the most thrilling routes to add on your Oregon road trip. This scenic route will leave you speechless with its contrasting landscapes of glacial gorges and barren deserts while taking you to elevations of nearly 10,000-feet.
• Capture a breathtaking panorama on the Wildhorse Lake Trail. The views of the glaciated valley and steep canyons offer one of the top vistas you’ll see on this Oregon road trip.
• Camp in the Alvord Desert to experience complete solitude in the Oregon wilderness. Make sure to visit Alvord Hot Springs to soak any aching muscles before hitting the road again.

• Wash off the dust from Oregon’s extensive desert by soaking in the relaxing Hart Mountain Hot Springs . Camping is free at the hot springs so make sure to arrive early if this is an overnight stay on your Oregon itinerary.
• Wander the hiking trails of the National Antelope Refuge and spot a plethora of wildlife in their natural habitat.
• Jump on your dirt bike or motorcycle to ride the desolate dirt trails cutting through the landscape.

• Go bird watching in the wetlands of the lake and marvel at the area’s geothermal wonders.
• Gaze at the sensational mountain scenery while you soak in the soothing pools at the Summer Lake Hot Springs.
• Drive the car out to Fort Rock for an enchanting sunset at this puzzling volcanic landmark.

RELATED: 

Exploring the Owyhee Canyonlands: Hiking, Rafting, & Camping

A Guide to Hart Mountain Hot Springs & What to Do in the Area

A Comprehensive Guide to Visiting Wallowa Lake State Park—Adventures and Camping

7 Awesome Things To Do in Sumpter, Oregon

• Rich’s Camp Cabin
• Eagle Cap Chalets
• Dreamers Lodge

Campgrounds: Wallowa Lake State Park | Strawberry Campground | Jubilee Lake Campground

RECOMMENDED OREGON ADVENTURE GEAR:

Tried and tested gear that we use around Oregon and the PNW!

Hiking and Camping

• Water Bottle Filter  
• Camping Stove
• Camping Cook Set
• Light 2-Person Tent
• Car Trash Bin
• Car Power Inverter
• Road Trip Duffel Bag
• Northwest Pass

Clothing Gear

• Hiking Socks – Men’s / Women’s
• Rain Jacket – Men’s / Women’s
• Hiking Backpack – Men’s / Women’s

Car Rental:

• Car Rental – Check here for deals
• Outdoorsy – For Vans, RV, etc

It’s safe to say all the above is just scratching the surface of what you can see on an Oregon road trip! With that said, everything mentioned above would take about a month to actually experience. Yep, a whole goddamn month!

Oregon is not a small state and it takes a long time to traverse.

I’d encourage you to check out our more specific Oregon road trips depending on the region you’re most interested in.

• 37 of the Best Oregon Hikes You’ve Got to Check Out

Each area mentioned above deserves at least a week of exploring. And when we say a week, we mean a week of actual exploring!

The driving can take up a really large chunk of the day so we’d advise you to tack on an extra few days on top of the week to account for driving or rest days.

Extending your road trip to our neighbors? Check these posts out!

• 19 Adventurous Things to Do on a Washington Road Trip
• 21 Adventurous Things to Do on a Northern California Road Trip
• If you’re looking to save a buck, download Gas Buddy App. As a rule of thumb, always fill up at the bigger towns when you can. The smaller towns often cost more, and if you pay by card, you may have a transaction fee on top of it.
• I’ll say it once more just in case, Oregon is not small! It will take you longer than you think to get places. I know my fellow Americans will get it but if you’re a visitor, our country and our states are insanely big. I can’t stress it enough, it will take you longer than you think.
• If you plan on visiting many of the places on this list, just get a parks pass instead of paying $5 randomly here and there for parking. The pass is $30 and you can display it and forget it.
• Bring food! Having to find food, particularly for breakfast and lunch, will eat up a considerable chunk of your day. Don’t waste hours on eating. Have snacks, sandwiches, and other quick things to munch on throughout the day and then save eating out for dinner.
• As far as budgeting goes, you can do this Oregon road trip on a modest budget. Many state parks have campgrounds that range from $15 to $25 per night. Check out these Oregon campgrounds .
• If you’re here in the peak season (summer months) campsites and hotels get booked out so make sure to book sooner rather than later.
• Be careful driving at night, particularly on the lonely roads. Animals like to come out and play. It’s best to keep your driving during daylight hours.
• If you’re coming to Oregon in winter , or even just before/after, be aware of road closures .
• For car rentals, we always check here .

More Road Trips

We hope this helped you plan some fun road trips in Oregon! Be sure to check out our other posts on road trips .

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I've been perpetually traveling and living around the world for years but it's hard to beat Oregon and the PNW. After years of road-tripping the area, I guess you can say I know it pretty well! When I'm not writing guides for you, you can catch me somewhere petting a dog, attempting to surf, hiking a volcano, or stuffing my face with bread and cheese.

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How to Plan an Incredible Oregon Road Trip (14 Days)

We were lucky enough to spend two whole months on a road trip around Oregon a few summers ago after we had to scrap our international travel plans, and it taught us an important lesson: you don’t need to fly halfway around the world to find wild and beautiful places – sometimes they’re right in your backyard the whole time . 

From purely a natural beauty perspective, Oregon pretty much has it all. A coastline on the Pacific dotted with rocky sea stacks and wide sandy beaches. A spine of mountains – the Cascades running down the middle of the state. The waterfalls of the Columbia River Gorge. The high desert in the eastern half of the state. A world-class wine region.

We could go on and on, but you probably get the idea by now.

That road trip cemented our belief that Oregon was the place we wanted to put down roots and create a home base after years of living on the road. 

Fast forward a couple of years from there, and we decided to make our forever home in Portland, Oregon, and that initial time exploring Oregon was a huge part of why we ultimately ended up making that decision.

In this complete guide to planning your Oregon road trip itinerary, we’re going to give you the logistics you need to know – when to visit and our recommended route – along with a mini guide to each place on the itinerary. 

We’ve written this guide for a two week trip, but at the end we’ll give you some ideas on how to shorten or lengthen the itinerary to fit your particular trip. 

Sound good to you? Let’s do it!

This guide is super detailed, full of our tips and favorite places based on our extensive experience exploring Oregon, which means it’s LONG. Strap yourself in, grab a cup of coffee (or beer or wine, no judgment here), and let’s get to exploring Oregon!

Disclaimer: Some of the links in this post, like hotel links, are affiliate links, meaning at no additional cost to you, we make a little bit of money if you click through and book. That being said, we would never recommend something to you that we don’t stand behind 100%.

How Many Days Do You Need for this Road Trip?

First of all, Oregon is a lot bigger than you probably think. It’s the 9th largest state in the country by square mileage, which is a fact that blew my mind. Driving between places can take several hours, if not more. 

Why do we bring this up? Because it has one major implication for your trip.

Unless you want to spend full days of your trip driving without stopping to see the scenery, you’re not going to be able to see the entire state .  

Fear not – we have a strong perspective on where you should focus your time if it’s your first trip to Oregon.

We really, really think that to do a full road trip around Oregon that includes both the northern coast and Bend, you need a full two weeks (14 days) . Otherwise, you’ll spend way too much time driving, and not enough time out exploring. 

Which is exactly how we’ve written the road trip below. As you’ll notice when you get there, the two week road trip we’re about to dive into features roughly a week on the east side of the Cascades, and roughly a week on the west side of the Cascades. 

The Cascades are the mountain range that run down the middle of the state, separating the temperate, western third of the state from the drier high desert in the eastern part of Oregon. 

If you have anything less than two weeks , we’d strongly recommend limiting your trip to either the mountains or the coast (perhaps with a day trip or two from Portland to explore them briefly). And we’d DEFINITELY cut the day trip to Crater Lake, because it’s a lot of driving to get there from Bend. 

If you have 7-10 days , we’d do a more focused road trip that follows a figure-8 with Portland at the center. Head east to the Columbia River Gorge, Hood River, and Mount Hood, then come back through Portland and head out to the Oregon Coast for a few nights, focusing on the stretch from Astoria to Tillamook. Here’s a map .

Alternatively, you could spend a week either on the Portland / Hood River / Bend portion of the loop, or spend a week on the Oregon Coast portion of the loop. 

If you do have less time, we have example itineraries for 7 and 10 day road trips below the main itinerary to help you organize your time. 

The Best Time to Do this Road Trip

This is a very, very important section in this guide, which is why it’s one of the first things we’re talking about. 

If you are interested in hiking in the Cascades – specifically near Mount Hood or Bend – your trip will need to be sometime between July and mid-October . 

Otherwise, high elevation hiking trails will be covered in snow, and some roads and trails will be closed. 

The exact timing depends on the year, precipitation, and spring temperatures (among other factors), but you will be most safe with a trip in August or September . That’s when roads are open, trails are largely snow-free, and you’ll be able to see everything you want to see.

During the summer and early fall, mountain passes and hiking trails are clear of snow, days are warm and sunny, the sun rises before 6:00 am and sets after 9:30 pm, and it’s an all around spectacular time to be in Oregon. 

The downside is that, in recent years, Oregon has been ravaged by forest fires during the summer, bringing a thick smoke that makes it really unhealthy and unpleasant to be outside. It’s hard to predict, but it’s something to be aware of if you’re planning a trip in the summer. 

Early fall is another great time to visit Oregon. The weather is, for the most part, still great (though it’s a little more unpredictable than summer). Unfortunately, there is still a chance of encountering wildfires in the fall.

In the spring, hiking trails at elevation – like around Mount Hood and Bend – are still going to be closed. If you’re into hiking, we’d definitely recommend waiting until later in the summer .  

If you’re visiting in the winter, we’d stick to the areas west of the mountains and do the Columbia River Gorge, Hood River, Silver Falls State Park, and the Oregon Coast . For what it’s worth, we’ve done the Oregon Coast multiple times in the winter, and it’s very moody (and wet). 

Here’s a map of what a winter road trip in Oregon might look like. 

Where to Start and End Your Road Trip

This one is easy – Portland! 

Portland is not really central in terms of the state – it’s up in the northwest corner – but it is central to some of Oregon’s best sights (the coast, Mount Hood, the Columbia River Gorge, etc etc) AND it has the best airport in the state (dare we say country?). 

Unless you live somewhere in Oregon or you’re driving from a neighboring state, the answer is Portland . 

The best option, with the most flights coming in and going out, is going to be our home airport – Portland International Airport (PDX) . 

The exception is if you have 10 days in Oregon and follow our road trip itinerary below. In that scenario, we’d recommend flying into Portland, and out of Bend (Redmond Municipal Airport, RDM) to save time on driving back to Portland just to catch a flight. 

Flights out of Bend will be more expensive and involve connecting through Portland or Seattle, but it’ll save you four (ish) hours of driving. 

One thing we were interested in prior to acquiring a van of our own is renting an Escape Campervan .

If you’re looking to experience the whole camping thing, but don’t want to sleep in a tent (to be clear, we’re all for tent camping), then a campervan might be for you!

Escape’s vans are all hand-painted, have full kitchens, and would be a lovely way to experience Oregon.

Escape has an office in Portland , which is where you’d pick up and drop off your van. 

How to Plan a Perfect 14 Day Oregon Road Trip Itinerary

With that in mind, here’s a summary of the 14 day road trip we’ll cover in detail below. 

• Day 1: Hood River and the Columbia River Gorge
• Day 2: Hood River and the Columbia River Gorge
• Day 3: Bend
• Day 4: Bend
• Day 5: Bend + Day Trip to Crater Lake
• Day 6: McKenzie River Scenic Byway
• Day 7: Newport & Around
• Day 8: Newport & Around
• Day 9: Tillamook & 3 Capes Scenic Route
• Day 10: Cannon Beach
• Day 11: Cannon Beach

Day 12: Astoria

• Day 13: Portland
• Day 14: Portland

Here’s a map of that route. 

We think this itinerary is a good blend of scenic drives (the Oregon Coast and the McKenzie River Scenic Byway are two of our favorites), cool towns (Astoria, Hood River, and Bend), and great outdoor adventures.

Which is basically everything we love about Oregon, packed into two weeks (minus some of the further out spots that don’t make sense here). 

Like we said, you can’t fit it all into one road trip. But we’ve done our best to include the highlights in hopes that you’ll fall in love with Oregon and come back a second (and third) time to explore more. 

Of course, that’s just the base itinerary that we’d recommend. The exact route you take is going to depend on your particular interests, what time of year you’re visiting, and more factors than we can possibly take into account here. 

We have ideas for shorter and longer itineraries below the main itinerary if you have more or less time. 

We’ll do our best to give you all the information you need to plan YOUR road trip in Oregon, but if we miss something or you have more questions, leave us a comment below and we’ll do our best to either answer your question, or point you to someone who can.

One last note: We have Portland at the tail end of the itinerary, because it’s a great place to end your epic road trip by kicking your feet up and eating and drinking your way through what we think is one of the best food cities in the country. You could just as easily put it at the beginning, it’s up to you!

Days 1-2: Hood River and the Columbia River Gorge

Drive Time / Distance from Portland to Hood River: 1 hour / 60 miles

Where to Stay in Hood River: Hood River has a very nice little downtown area, but there aren’t that many places to stay downtown. We actually like staying across the river in Washington, either at the Society Hotel in Bingen or at the incredible RubyJune Inn (a very charming B&B in a tranquil setting run by lovely people). 

The Columbia River Gorge runs along the northern border of Oregon (it separates Oregon from Washington State), and has the highest concentration of waterfalls in the state. 

Depending on how good your memory is (and how long ago high school was for you), you may remember the Columbia River from your days learning about Lewis and Clark, because it’s the river that they came up as they made their way out to their final destination just south of Astoria. 

Living in Portland, the Columbia River Gorge is essentially our backyard. It takes 30-40 minutes for us to get out there, and when we’re looking for an easily accessible hike for a random Thursday morning, this is generally where we’re heading. 

It’s also on our itinerary for every single first-time visitor who comes to Portland to visit us. 

There is a nice mix of different hikes in the Columbia River Gorge , from easy waterfall hikes to hikes that climb to the rim of the Gorge, where you’ll find dramatic vistas out over the Columbia River and the Gorge beyond. 

Hood River is a town in the Columbia River Gorge, and it is perched at a crossroads of sorts. It sits at the point where the wet, temperate climate of western Oregon transitions to the dry, more extreme climate of the high desert in eastern Oregon. 

To the west, you’ll find some of the best waterfalls in Oregon. To the east, the high desert. And both north and south are the Cascade Range, and places like Mount Hood and Mount Adams. 

There are a bunch of great things to do in Hood River, and that list grows longer when you include the fertile Hood River Valley with its fruit trees as far as the eye can see and the wineries along the Columbia River. 

Hood River is a great home base to use to explore the Gorge and the fertile Hood River Valley, which is what you’ll be doing for this stretch of the itinerary. 

Note that we’ve split the “what to do” sections below into Hood River and the Columbia River Gorge to make it easier for you to plan and group things together. In this case, you’ll hit the Gorge coming from Portland first, then tackle the things around Hood River once you’re already through the Gorge. 

What to Do in the Columbia River Gorge

Here are our favorite stops in the Columbia River Gorge.

Wahclella Falls : This is the best bang-for-your-buck waterfall adventure in the Columbia River Gorge, we think. Multnomah Falls is great, yes, but it’s an absolute zoo at all hours. The short and easy hike out through a canyon with steep rocky walls here weeds out most of the visitors, and you end up at a beautiful waterfall that tumbles off of a ledge into a pool 65 feet below. 

Drive The Historic Columbia River Highway: The Historic Columbia River Highway runs from the town of Dodson, just west of Bonneville (and the dam of the same name), all the way to the town of Troutdale, which is just east of Portland. It’s a windy two lane road that parallels I-84, and is the original road that was used to traverse the Gorge on the Oregon side. Our recommendation would be to drive it from Multnomah Falls to its western terminus, because there are routinely huge traffic jams along the road at the base of Multnomah, and it’s better to park in the big lot along I-84. 

Multnomah Falls: Multnomah Falls is the queen of the waterfalls in Oregon. It’s by far the most impressive waterfall in the state, we think, and it’s actually the biggest tourist attraction in Oregon thanks to its location about 40 minutes away from downtown Portland. It’s a two-tiered waterfall that, all-in, falls 620 feet down from the top of the rocky ledge high above the viewing platform. The only issue we have with Multnomah Falls is the fact that, at any given moment, you’re likely to be sharing the experience with around 1,000 of your closest friends. It’s worth seeing, but there are so many other waterfalls in the Gorge to get to with a fraction of the visitors (especially if you’re willing to hike a little bit). Definitely park at the bigger parking lot along the freeway ( here on Google Maps) – the smaller lots at the base of the falls are an absolute nightmare, and we’ve seen massive backups along the Historic Columbia River Highway of people just waiting to get a spot. The bigger lot has more parking, and you just have to walk a few hundred feet to get to the falls. 

Latourell Falls: Lower Latourell Falls is one of the most scenic waterfalls in the Gorge after Multnomah, particularly in the winter when the water level is high AND there’s a bright greenish-yellow moss covering the rocks on either side of the falls. The lower falls is the more impressive, we think, as it falls 225 feet off of a ledge in one single drop. There’s a nice wooden bridge at the base of the falls, which is a short hike from the trailhead, that is a must-do and is a good spot for pictures. There’s a nice, relatively easy two mile loop hike that takes you up to the Upper Falls and down around to the base of the lower falls that is a worthy excursion if you have the time and energy. 

The Vista House & Portland Women’s Forum Scenic Viewpoint: These are two excellent viewpoints at the western end of the Historic Columbia River Highway to cap off a day full of great views. Pictures are worth 1,000 words here, we think, so here’s a few we’ve gotten from up here. 

What to Do Around Hood River

Here are a few of our favorite things to do in and around Hood River.

Tamanawas Falls: This excellent waterfall hike is on the eastern slopes of Mount Hood, and would be a great stop between Government Camp and Hood River. It’s right on Highway 26, and it’s a nice, easy hike up to a spectacular waterfall. Parking is limited, so you’ll want to get there early, or be prepared to wait for a spot in the tiny lot – parking along the highway is illegal, and we’ve seen many people get tickets here. You can find more information about this hike – which is one of our favorites – over in our Tamanawas Falls trail guide .

Drive the Fruit Loop: The Hood River Fruit Loop is a perfect half-day activity near Hood River that takes you through the fertile Hood River Valley, with apple and pear trees as far as the eye can see (with backdrops of Mount Adams, Mount St. Helens, and Mount Hood). There are a bunch of worthwhile stops here, but our favorite is Draper Girls Country Farm , which does u-pick cherries for a short window in the summer, and has all around excellent produce more or less from spring to fall. They have a lovely back patio area with great views of Hood, and a lush collection of various fruit trees. Plus, a wide selection of locally made jams, honeys, and other stuff inside the shop. 

Wine Tasting near Hood River: The area around Hood River, both on the Oregon side of the Gorge, and on the Washington side, is a great place to grow grapes and make wine. There are a bunch of wineries in Hood River itself ( Hood River Common House is a good spot), but the real way to do it is to hop in the car and drive out to one of the wineries dotting the landscape around Hood River. We like the Gorge White House (not the best wine and cider, but the setting is amazing) and Loop de Loop (the friendliest wine makers and the best dog, plus an amazing view), and have also heard good things about AniChe Cellars , Le Doubblé Troubblé , and Analemma Wines (this one came highly recommended from the folks at the Ruby June Inn, where we stayed on our recent trip). 

Days 3-4: Bend

Drive Time / Distance from Hood River to Bend: 2 hours 45 minutes / 140 miles

Where to Stay in Bend: This choice basically comes down to whether you want to be downtown in the heart of all the action, or in a quieter locale. Stay at the Oxford Hotel in Downtown Bend for the best location in the middle of the action. Stay at LOGE Bend – we’ve stayed at other properties they own before – if you want to be right near the Cascade Lakes Scenic Byway.

Over the past decade or so (though it seems like it happened overnight), Bend has gone from being somewhat on the map, to being one of the most famous outdoor destinations in the western United States. 

As you drive through the Cascade Mountains into the heart of Central Oregon, you’ll notice that the landscape starts to change.

First you hit the eastern foothills, which are notably more dry than the western foothills, and as you continue to Bend and beyond, you’ll be right in the heart of the high desert that stretches across Central Oregon. 

Bend is perched in the eastern foothills of the Cascades, and it is situated between the lush evergreen forests that cover the western part of the state, and the high desert that covers most of central and eastern Oregon. 

Remember at the beginning of this guide, when we said that Oregon is the ninth biggest state in the country? Bend is about 25% of the way from the western border (the coast) to the eastern border with Idaho. Which means the high desert stretches for a LONG time from Bend to the east. 

Bend is perfectly placed between the mountains and the high desert. Within 45 minutes or so, you can be in the heart of the alpine paradise in the Cascades, or hiking through the desert dodging rattlesnakes in Smith Rock State Park (more on that in a second). 

What to Do in Bend

Here are some things to do in Bend, including some of the things to do just outside of town along the Cascade Lakes Scenic Byway. 

Hikes Around Bend: Within the Bend city limits, there are a few good hikes (we’re not counting the hikes in the mountains or at Smith Rock, which we have separate sections for below). Pilot Butte is right in the middle of town, and after a quick ascent you have a panoramic view of the surrounding landscape that serves as a nice introduction to Central Oregon’s geography. To the west, you’ll be able to see the snow capped peaks of the Cascades (there’s a topographic map to help you identify which peak is which). To the east, it’s a lot of flat land. We also have hiked sections of the Deschutes River Trail , which heads south out of town along the river. You could follow the trail for miles and miles, but there’s a nice 2.7 mile loop that focuses on the part of the trail near the Old Mill District that would be a lovely way to spend a morning. It would look something like this . If you want something a little longer, continue south from Farewell Bend Park, which is where the trail gets a little less developed. For more information, read our guide to hiking in Bend .

Explore Downtown Bend: Downtown Bend is centered around Drake Park along the Deschutes River (there are several areas that could be confused as “downtown” so we wanted to clarify). There’s also the Old Mill District, which is a little bit south (and has more chain retailers and Red Robin vibes, if you know what we mean), and the Box Factory, which is between them. In downtown Bend, go to Lone Pine for coffee, The Lemon Tree for brunch (it’s popular so go early), and Bonta for gelato. Then, poke your head into the many shops and boutiques along NW Wall and NW Bond. 

Brewery Hopping: Bend, like Portland, is known for its breweries. And like Portland, there are way, way too many breweries to visit in just a couple days. Here are a few that we like for one reason or another.

• Deschutes Brewing : In many ways, the OG Craft Brewery in Bend that set off the craft beer craze in Oregon. It’s still owned by the original owners (rather than Anheuser-Busch), which is cool. They do tours (which we’ve done and enjoyed), and they have an onsite taproom with beers that you can’t find elsewhere.
• Silver Moon Brewing : A cozy taproom outside of town – we like them for their Thursday trivia nights! They have a cool space that has both indoor and outdoor seating with a lineup of live music in the summer. They also have a couple of food trucks onsite.
• Crux Fermentation Project : Our friends who are beer nerds think this is the best beer in Bend (though they also note that there’s too many and they’re too different to really choose). What we like about them is their HUGE outdoor terrace, which is a perfect place for some cold beer after a morning of hiking.  

Cider in Bend: If you’re more into cider (we are!), the small town of Tumalo just north of Bend has a couple of our favorite cideries in Oregon, and they’re just around the corner from each other. The first is Tumalo Cider , which has a nice taproom and great, dry ciders. The second is Bend Cider Company , which has a new-ish taproom a couple of blocks away. They do fun flavor combinations featuring fruits and botanicals (but not too sweet!) – we liked the Blackberry Ancho we tried recently. There’s a food cart pod across the street from Tumalo Cider which would make a good stop for lunch between cider tastings.

Tumalo Falls: Honestly, the hike to Tumalo Falls kind of sucks. But the waterfall is cool, so there’s that! It’s a 97 foot high plunge into Tumalo Creek, and if you do the six mile hike, you’ll reach the viewing platform and realize that it’s a five minute walk from the upper parking lot. We’d drive to the parking lot and check out the falls, saving your energy for a more interesting hike (there are many!) later. 

Explore the Cascade Lakes Scenic Byway: This scenic drive (also known as Highway 372) leaves Bend, heading southwest out into the alpine paradise that is Deschutes National Forest. Skiers and snowboarders familiar with Oregon will know this stretch because it takes you out to Mount Bachelor, one of the state’s premier skiing destinations. Which, if we think about our other favorite hiking spots in the Pacific Northwest, is a great indicator of a good summer hiking destination (multiple of our picks for the best hikes in Oregon are along this stretch). It’s worth spending a day driving the byway, starting in Bend and working your way down to Elk Lake before returning the way you came. You could also do a loop, taking NF-40 back towards Bend, but we’d prefer driving the more scenic byway both ways. This is a very popular stretch, and there is a permit you’ll need to enter during the peak summer season. The Cascade Lakes Scenic Byway is full of great hikes, particularly as you get out past Mount Bachelor. Here are a few good ones:

• Green Lakes Trail: Potentially our favorite hike in central Oregon (technically it’s in the Cascades, so does that count as central Oregon?), this hike has everything we love about hiking in the Cascades. Following a babbling creek the entire way, which is the perfect white noise for a hike? Check. Pristine alpine lake (really, lakes)? Check. All sorts of peaks to admire? Check. It’s 9 miles, but it’s an easy 9 miles, we think.
• Tumalo Mountain Trail: A tough ascent, but the views from atop Tumalo Mountain are worth the sweat. You’ll have Mount Bachelor, the South Sister, and Broken Top right in your face, with various other peaks peeking out behind them. It’s basically straight up, straight down.
• If you’re really up for a challenge, there are two excellent but difficult hikes here: Broken Top & No Name Lake and the South Sister . Both are very difficult, and should not be underestimated. The South Sister is going to be better if you can backcountry camp the night before at Moraine Lake or Green Lakes, which cuts down your ascent (but requires an extra night of backpacking, and all the associated gear). 

Sparks Lake: We love Sparks Lake. The photo below was taken there on an early summer morning just after sunrise. Head to the day use area, park, and walk along the southeastern shore of the lake, where you’ll be treated to an absurdly good view of the South Sister and Broken Top, with a reflection in the still water of the lake if you’re lucky. 

Smith Rock State Park: With its winding river snaking its way between orange-hued rock formations, Smith Rock looks like it belongs somewhere in Utah or Arizona, not in Oregon. There’s really only one hike in Smith Rock State Park – though you can do it two ways – and that’s the Misery Ridge Trail . It’s accurately named, because the initial ascent up to Misery Ridge is brutal, especially on a hot summer day with full exposure to the sun. The views from the top of the ascent, though, are worth the price of admission. You’ll have a panoramic view of central Oregon, with the snowy peaks of the Cascades to the west, and the high desert stretching out as far as the eye can see to the east. On the descent, you’ll pass Monkey Face, a very popular destination with rock climbers. It is also accurately named, because from a certain angle, this rock formation looks exactly like the face of a monkey. The trail descends back down to the river, where you can either head left to return on the River Trail (shorter and flatter) or right to continue on the Summit Trail (longer with better views and more climbing) to finish the loop. It’s about 30 minutes north of Bend, and you can do it on the way from Hood River to Bend because you’ll drive right by it. 

Day 5: Day Trip to Crater Lake (from Bend)

Drive Time / Distance from Bend to Crater Lake (one way): 1 hour 45 minutes / 90 miles

So you want to add Crater Lake National Park to your Oregon trip?

Well, we have good news and bad news. 

The good news is that it’s totally doable as a day trip from Bend. 

The bad news is that it’s only really accessible for a few short months a year, and it’s not really convenient even when it’s at its most accessible. It’s at the southern edge of the state, and it’s fairly far from just about everything else on this itinerary.  

To add Crater Lake to this particular itinerary, you’re going to want to do it as a day trip from Bend. It’s about 90 minutes from Bend to the north rim of Crater Lake, which doesn’t seem so bad, right?

However, there is one major caveat here, and that’s the fact that the rim road that circles around to the north end of the rim is closed during the winter and early spring due to snow. 

It will start to open in early spring, but when exactly that happens totally depends on the year. 

That’s an issue to keep in mind because Bend is north of Crater Lake. The only way to access the small slice of the park that’s open between November and April (roughly), which is on the south rim, is to enter the park through the south entrance. Which is about three hours from Bend. 

We would only really recommend adding Crater Lake during the summer and early fall (call it June through October) when roads will be mostly open, and hiking trails will be mostly snow-free.

What to Do in Crater Lake National Park

Here are our favorite things to do and see in Crater Lake National Park. 

Drive the Rim Road All the Way Around the Lake: This may be obvious, but if the rim road is open all the way around the lake (July through October), you should drive it all the way around, and stop for pictures at the various pull outs along the way. 

Hike to Mount Scott: The hike up to Mount Scott is very exposed, and we’d highly recommend putting this first on your itinerary to do it before it gets really hot. However, it brings you to a ridge with an old fire lookout that represents the highest accessible point in the park. From there, you’ll have excellent views out over the lake and beyond, including some of the peaks of the Cascades like Mount Thielsen. 

Hike Down to Cleetwood Cove: Mount Scott takes you up to the highest accessible point in the park, and Cleetwood Cove is the lowest point, getting you down to the water. It’s a very steep hike that is tough (it’s short, but very steep), but it’s worth it to stick your feet in the cold, sapphire blue water. 

Hike a Portion of the Discovery Point Trail: Leaving from the main visitor center, the Discovery Point Trail takes you along the southwest rim of the Crater with some truly jaw dropping views out over the lake to be had for a relatively easy, mostly flat walk.

Day 6: The McKenzie River Scenic Byway

Drive Time / Distance from Bend to the McKenzie River: 1 hour 30 minutes / 75 miles

The McKenzie River Scenic Byway follows the path of, you guessed it, the McKenzie River, which is one of Oregon’s many important rivers.

For your purposes, we’d recommend driving from Bend out to Sisters, then connecting with the most scenic part of the drive along Highway 242 (which is closed in the winters, and once you drive it you’ll understand why).  

It’s a gorgeous drive, littered with waterfalls, tight switchbacks, alpine lakes, and lava flows. 

There are a few things you need to know about this stretch. First, it’s closed outside of summer and early fall (usually open between July and October).

Second, it’s a narrow two lane road with lots of switchbacks, so it might not be best for RVs or trailers . 

Also, if you follow this itinerary as we’ve written it, you’ll be approaching from the east (coming from the Bend area). We’ve organized the stops from east to west for that reason. 

What to Do Along the McKenzie River Scenic Byway

Here are some stops to make along this scenic drive. 

Sisters: Sisters represents the end of the McKenzie River Scenic Byway, and the beginning of central Oregon and the high desert, which stretches for hundreds of miles to the east until you get into the Wallowas in eastern Oregon. Sisters itself is a cute little town that’s a great base for adventures into the nearby Three Sisters Wilderness. It’s a vaguely western-themed town, with some great spots to eat and drink ( Sisters Coffee and Sisters Meat and Smokehouse are good stops) and a cute little downtown area where you can do some window shopping. 

Scott Lake: This pristine lake is one of the spots we’re hoping to return to this summer. It’s a gorgeous lake with a perfect reflection of the Three Sisters (really two of the three sisters), one of the most distinctive natural features of central Oregon, and a bunch of first come, first served campsites along the lakeshore. However, the tradeoff here is the mosquitoes, which are intense in the early summer. For your purposes, we’d park along the lake and walk out to the western shore to get that reflection picture. It’s best in the afternoon, when the sun is behind you. 

The Dee Wright Observatory: As you ascend the tight switchbacks along the road passing Scott Lake, you’ll notice an abrupt change in the landscape. In what seems like a few minutes, you’ll go from dense evergreen forests to an open, rocky landscape. That shift is a result of a massive eruption of the Belknap Crater two millennia ago, and that dark rock stretching out as far as the eye can see is the resulting lava flow. The Dee Wright Observatory is an excellent stop not only to admire the lava flows, but because it gives you a great overview of the numerous rocky peaks surrounding you. This, my friends, is the heart of the Cascades in Oregon, and you’ll see the Sisters, Broken Top, Mount Washington, and Mount Jefferson, along with a handy key atop the Observatory to help you identify which is which. 

Proxy Falls: Over the course of this trip, you’re going to see a bunch of incredible waterfalls, especially as you get into the Columbia River Gorge later in the itinerary. Proxy Falls will likely be in your top three. It’s a short hike – roughly 1.5 miles – that takes you to a massive waterfall that cascades down the mossy rocks into Proxy Creek. You can do a loop that takes you to both Lower Proxy Falls and Upper Proxy Falls. The lower falls is the more impressive of the two, and the view from the base is incredible. 

Days 7-8: Newport & Around

Drive Time / Distance from the McKenzie River to Newport: 2 hour 45 minutes / 145 miles

Where to Stay in Newport: We haven’t stayed there ourselves yet, but the Inn at Nye Beach has been on our list for years now. 

Full disclosure here, this part of the itinerary requires a long drive to get out to the coast, but we think it’s worth it because the drive connects two of our favorite parts of the entire state. 

We went back and forth on whether or not to add a night here in Eugene, which would cut down on the drive time, but ultimately we think your time is better spent on a long drive today to give yourself some extra time in other places (which we think are more worthy of your limited time than Eugene).  

Newport is the biggest city on the central Oregon Coast, and has the best selection of places to stay, restaurants, and other amenities like grocery stores before you get into the more rural southern Oregon Coast. 

The structure for today is essentially using Newport as a home base to continue your road trip south along the coast past Newport (which is one of our favorite stretches of the Oregon Coast) and then returning to Newport for the night to set yourself up for a long drive the next day. 

Just south of Newport, the coast starts its transformation from the very developed, very tourist-friendly northern Oregon Coast to the more rugged southern Oregon Coast, which is rockier, less-traveled, and offers a little more peace and quiet than places like Cannon Beach and Seaside. 

From Newport, you can hit one of the most scenic drives on the coast – the area around Cape Perpetua and Heceta Head – before returning to Newport for the night to eat some fresh seafood and check out one of the many beaches in town. 

What to Do Around Newport

Here are our favorite things to do in and around Newport. 

Devil’s Churn: A short stop where you’ll hike down to an overlook with a view of an inlet that is partially covered at the end. Which means at high tide, if you’re lucky, the waves coming in will meet the waves going out and create an explosion of water.  

Cape Perpetua: The view from the top of Cape Perpetua is one of our favorite views on the coast, and it reminds us a lot of Big Sur down on the California Coast (at least on a sunny day). You can hike from the lower road up to the top , which is a nice workout, but you can also just drive to the top (which we didn’t know until we got up there, sweaty and huffing and puffing). There really isn’t a reason to do the hike other than a workout – there aren’t any additional views you get by hiking. 

Heceta Head Lighthouse: This is one of the most beautiful lighthouses on the coast, and it’s easily accessible from the parking lot. It sits on a 1,000 foot headland that towers over the Pacific, and they have tours of the lighthouse, a charming B&B in the old light keeper’s home, and tidepools and trails to explore. You can hike out to Hobbit Beach from the lighthouse, which is a nice little trail that follows the coast to a sandy beach. 

Sea Lion Caves : We drove past this place on our first trip, saw a line out the door of a tiny little touristy-looking hut, and said “look at those suckers!” Then we learned what it actually was later on from some Oregonians, and were at least a little bit disappointed that we didn’t stop in. If you want to see sea lions, this is the place to do it. That hut sits over an elevator that takes you down hundreds of feet to the water level, where there’s a sea cave – America’s largest, in fact – filled to the brim with barking sea lions. They’re open 9:00 am – 4:00 pm 363 days a year, and it costs $16 for adults, $10 for kids (under 4 are free!), making it a little bit pricey. 

Exploring Newport: Newport is probably best known for its world-class aquarium – the Oregon Coast Aquarium – which we stopped at and immediately turned around when we saw the flood of small children (it would be a good family activity, though!). There are two lighthouses in town, and the Yaquina Head Lighthouse is at the northern end of town, and is well worth a stop (the Yaquina Bay Lighthouse is less impressive). Definitely head down to the charming Historic Bayfront for dinner and the shops there ( here on Google Maps) and head out to Agate Beach ( here on Google Maps) for a good view of the lighthouse. 

Day 9: Tillamook and the Three Capes

Drive Time / Distance from Newport to Tillamook: 1 hour 30 minutes / 70 miles

Where to Stay in Tillamook: Tillamook itself isn’t really the nicest city, but there are some good places to stay up and down the coast from town. We stayed in one of the tiny homes at Sheltered Nook , which is just north of the city, and really liked it (full kitchens, nice outdoor seating). 

Everyone who has spent any significant amount of time in the Pacific Northwest knows Tillamook because of the cheese, ice cream, sour cream, or some other dairy product that every supermarket carries. 

And while you’re in Tillamook, you should definitely visit their factory for a tasty, educational experience. 

However, Tillamook is also home to the Three Capes Scenic Route, which is well worth a half day of your time to explore as well. 

The drive from Newport to Tillamook is nice, and features a couple of our favorite hikes on the Oregon Coast – Cascade Head and God’s Thumb – which are both worth a stop along the way. 

What to Do Around Tillamook

Here are three things not to miss when you’re in Tillamook. 

The Three Capes Scenic Route: Like we mentioned above, this is probably the premier thing to do near Tillamook. The Three Capes Scenic Route covers a 30 mile stretch of the Oregon Coast from Cape Meares to Cape Kiwanda (Cape Lookout is between them, and rounds out the “Three Capes”) where you’ll have great coastal views around every bend in the road. If you’re following this itinerary as we’ve laid it out, you’ll be heading north to south.

• Cape Meares is your first stop, and there are two things to check out. First is the Cape Meares Lighthouse, which is the shortest lighthouse on the Oregon Coast. However, it has an impressive lens that was installed in 1890. The second thing not to miss is the Octopus Tree (it’s a weird looking tree with eight branches, hence the name) and the viewpoint right past it that looks out over the beaches to the south, including Short Beach. It’s a quick walk from the main parking lot.
• Cape Lookout is your next stop, and is our personal favorite of the three. The highlight, by far, is the hike out to Cape Lookout . It’s a relatively easy hike that hugs the cape, which narrows as you get further and further out onto it before the trail ends at its western tip, where the views are amazing and you can hear the seals frolicking on the rocks below. It’s also a good place for whale watching in spring, because it’s about as close to the migrating mammals as you can get.
• Cape Kiwanda is the last of the three capes, and it’s a little different. It’s very popular with surfers, and you can drive out onto the beach, which means it’s a slightly different crowd that includes fishermen and boaters. From the parking lot, the main attraction is up and to the right of the beach, where you can hike up onto the cape for some great views in both directions. You’ll be hiking up in deep sand, so it’s harder than it looks. Make sure to catch the hang gliders, if they’re out, who use the northern end of the cape as a jumping off point. 

Hiking in Lincoln City: Technically this isn’t Tillamook – it’s 30-45 minutes south – but we’re including it here because two of our favorite hikes on the Oregon Coast are in and around the sleepy coastal community of Lincoln City. The first is Cascade Head , which is maintained by the Nature Conservancy (no dogs allowed). It’s a great hike that climbs through the forest and emerges onto a (very windy) bluff over the ocean, which you can climb up for some excellent coastal views. It’s windy as you get out onto the coast, so be prepared. The second is God’s Thumb , which is a short hike from the north end of Lincoln City that takes you out to a point, which looks out over the Oregon Coast both north and south. Along the loop, you’ll pass the Knoll, where you’ll have a view of the never ending sandy beach that stretches out to the south. 

Tillamook Cheese Factory: The Tillamook Cheese Factory is legendary. Not only is there a cool educational experience where you can see how they make the cheese, but there are some truly great food options, including a huge ice cream scoop shop. If you’ve never had their ice cream before, it’s incredibly creamy. That’s their whole thing. The chocolate peanut butter swirl is Alysha’s favorite, with thick, salty swirls of peanut butter tucked into their chocolate ice cream.They also have a retail store here, where you can buy all of their cheeses, including some of their hard-to-find reserve varieties, along with a selection of other local products. If they have them, do not miss their cheese curds, which are only available at the factory and are incredible (we’d never had them before we bought them a few years ago and fried them up post-hike over our camp stove – incredible). 

More Cheese: There’s actually a second cheese destination down the road – Blue Heron French Cheese Co – though we weren’t nearly as impressed with the presentation. The cheese – which leans towards French style – is really good, though. 

Days 10-11: Cannon Beach

Drive Time / Distance from Tillamook to Cannon Beach: 60 minutes / 40 miles

Where to Stay in Cannon Beach: For Cannon Beach, you have two choices – on the beach (more expensive, nice experience) or a few blocks away from the beach (cheaper, less romantic). We’ve stayed at the Inn at Haystack Rock twice, which falls in the latter category and is nice enough (but probably needs a bit of a facelift in the next couple of years). 

Cannon Beach is one of the most popular day trips from Portland , because it’s a mere 90 minutes from downtown Portland. As a result, the area can feel unbearably overcrowded on summer weekends, as Portlanders (us included) flock to the coast to escape the inland heat. 

However, on a weekday or early in the morning and later in the evening, Cannon Beach is a lovely place to spend some time.

We recently went out to Cannon Beach – our first beach foray with our dog, Lupine – midweek in January, and we were basically the only people on the hiking trail in Ecola State Park. It was wet and muddy, yes, but it was so peaceful. 

The highlights in Cannon Beach are actually the state parks that border the town on the north and south end, Ecola State Park and Oswald West State Park .

Sure, Cannon Beach – the town AND the beach – is nice, and you should definitely do a sunset walk on the beach. But definitely don’t miss the nearby state parks.  

What to Do in Cannon Beach

Here are some Cannon Beach highlights that you really shouldn’t miss. 

Ecola State Park: Ecola State Park was closed for years and years until very recently, when it was reopened to the public. As you drive in on the windy, tree-lined road, it’s easy to see why a few bad storms put the park out of commission for a couple of years. This park is one of the most popular destinations on the Oregon Coast, so it’s likely to be busy if you’re here in the summer or on a weekend. Get there early to get a parking spot in the relatively small lots! There are two things not to miss in Ecola State Park, we think. 

• The first is Crescent Beach , which is a short hike accessed either from the main parking lot, or by walking into the park from Cannon Beach. From the main lot, which you should visit whether you do the hike or not for the views, it’s a short downhill hike that winds through the ferny forest before an aggressive descent down to the beach. The beach is best at low tide, when it’s wide and sandy and littered with driftwood and sea stacks. Basically, everything you could possibly want in a Pacific Northwest beach.
• The second is Indian Beach . There’s a parking lot right at Indian Beach that fills up early because it’s a popular surfing destination. You can also hike out to Indian Beach from the main parking lot in the park, which is worth doing for the coastal views along the way. 

Hiking in Oswald West State Park: This is the other Oregon state park we referenced above, and it’s equally worthwhile. There are three hikes here to focus your time on. First is the hike to the top of Neahkahnie Mountain , which is an aggressive ascent up switchbacks to a viewpoint where you can see miles and miles of coastline to the south. Second is the hike out to Cape Falcon , which navigates out to the cape on the north side of Short Sand Beach, where you’ll have excellent views back towards the beach. Be aware that this hike is almost always extremely muddy. Seriously, do not underestimate the mud, even in the early summer. Third is the hike – though it’s more of a leisurely walk – out to Short Sand Beach , which is a wide sandy beach (at low tide, anyway) that is very popular with surfers. 

Haystack Rock: It’s cliche, but Haystack Rock really is an impressive sight, especially if you’re not used to the towering sea stacks that you find up and down the Oregon and Washington coast. In fact, we’d argue that Haystack Rock is up near the top of the list of tourist attractions in Oregon, somewhere below Multnomah Falls and above Powell’s Books in Portland. It’s a huge sea stack, rising 235 feet out of the surf to tower over the beach and surrounding community. It’s particularly spectacular at low tide, when you get some cool reflections in the wet sand. On our first trip to Cannon Beach, we witnessed a pair of Bald Eagles raiding the resident puffin colony for their eggs! It was quite the drama, and there are rangers on the beach in the summer who talk about the puffins and the attempts to keep them alive. 

Drive Time / Distance from Cannon Beach to Astoria: 45 minutes / 25 miles

Where to Stay in Astoria: You want to stay centrally so you can walk to the attractions downtown. We stayed at Norblad Hotel on our last trip, and liked it (nice location, stylish rooms, comfy beds). 

Astoria is a fitting stop on this itinerary, because in many ways, it’s where the state of Oregon as we know it today began.

Lewis and Clark National Historical Park, which is just south of the city center, is near the location where Lewis and Clark made camp for three months, having completed their mission to find the Pacific Ocean. 

Now, you might be thinking that Lewis and Clark, who had completed their ultimate goal after a significant chunk of time spent struggling west from St. Louis, might have been celebrating with their feet up. 

But their arrival and stay happened to be smack dab in the middle of winter – from December through February – so rather than celebrating with the long, warm days of an Oregon summer, they were treated to constant drizzle and less than eight hours of sunlight. FUN. 

Anyway, Astoria is meaningful in many ways, from the early 19th Century and Lewis and Clark’s antics, to the time when John Jacob Astor tried to make Astoria the New York City of the west (he almost had it!). 

Today, it sits at the northwestern corner of Oregon, and is home to what has to be the highest number of breweries per capita in the country (there’s four or five, and Astoria is tiny), and filming locations for some of the iconic films of the 90’s (the Goonies and Kindergarten Cop, among others). 

What to Do in Astoria

Here are some of our favorite things to do in Astoria. 

Lewis and Clark National Historical Park : Like we mentioned, Lewis and Clark National Historical Park is near the site of Fort Clatsop, which is where they set up camp for three miserable months before heading home to report back to Jefferson. There’s a model of Fort Clatsop here, a bunch of fun information on what life was like on that expedition (and some very charismatic rangers eager to share anecdotes like the one above), and a hike that connects the fort with the coast, a route that they covered many times. However, the hike isn’t really worth too much of your time – it’s 6.5 miles one way out to the coast – we’d do the first mile or so, enjoying the ferny forests of sitka spruce trees before heading back. 

The Astoria Column : The Astoria Column is perched up on the hill above town with a commanding view out over the Columbia River and the famous Astoria-Megler Bridge – that’s the green bridge crossing the river to the Washington side. The Column is an interesting piece of art, because it is wrapped in the story of Astoria. It’s hard to see the artwork when you’re standing at the base looking up at it, but there’s a digital re-creation with labels that is helpful to understand exactly what you’re viewing. You can climb to the top of the column for an even more impressive view of the river. It costs $5 to park in the lot at the Column, or you can park at the base of the hill in town (roughly here ) and hike the Cathedral Tree Trail up for free. 

Fort Stevens State Park : This is the northwest corner of Oregon, and also – fun fact – the site of the only attack on a military base in the contiguous United States since the War of 1812 (the Japanese shelled it a few times in 1942). It’s an Oregon State Park, though it was a military base through the early 20th Century. Today, the bunkers are one of the main draws here, and are particularly interesting when there are rangers and volunteers out there to tell you stories about the local history (which is usually on weekends in the summer). It’s worth driving out to the coast and hitting the wreck of the Peter Iredale , a shipwreck on a wide sandy beach, and Clatsop Spit at Lot C ( here on Google Maps) where you can walk out along the rocks on the Pacific. 

The Breweries: Two of Oregon’s best breweries are up in Astoria – Buoy Beer Co and Fort George Brewing – and are basically a must-stop for any beer aficionados who find themselves in the state’s northwest corner. They each have a taproom within walking distance of the main drag, and both have food menus and extensive taplists, with many beers you’re not going to find outside of the taproom. In addition, there are a few smaller breweries (like Fortune and Glory Cider Company – technically not a brewery, I guess). Across the street from them is Bridge & Tunnel Bottleshop & Taproom , the best beer bar in Astoria (and a good place to try multiple beers from different breweries). 

Days 13-14: Portland

Drive Time / Distance from Astoria to Portland: 2 hour / 98 miles

Where to Stay in Portland: Portland is by far the biggest city in this guide, so we’d recommend reading our in-depth guide to choosing a place to stay in Portland for the information you need to make the best choice for you (which takes more than a couple of sentences).

What can we say about Portland? We have fallen head-over-heels in love with our new home. Everyone always talks about the “weirdness,” which we have come to understand as an implicit permission to be whoever you want to be. 

That idea flows through to the unique small business culture that exists in Portland, where you can find all sorts of locally made foods, crafts, and home goods.

The funny part about Portland is that there aren’t really any big name tourist attractions. Seattle has the Space Needle, San Francisco has the Golden Gate Bridge, and Portland has… a donut shop and an independent bookstore?

But, honestly, that’s kind of why we love it. It’s not that there isn’t a lot to do – there’s plenty of amazing things to do in Portland. 

The food scene? The best on the west coast (except for maybe L.A.). There’s a culture of innovation – which we think is at least partially driven by the food cart scene that allows for low-cost experimentation (versus opening a brick and mortar location). 

The access to the outdoors? Between the excellent parks in Portland and the access to the mountains, Gorge, and coast, it’s hard to beat.

We’re in love with our home, and think you’ll like it too. 

Unfortunately for you, your time here is limited, and we’ve intentionally chosen to weight this road trip towards Oregon’s natural beauty, which means you’re left with about a day, maybe a day and a half to explore the biggest city in the state.

If you have an extra day or two, it’s absolutely worth adding time here.  

What to Do in Portland

Now, there are way too many things to list here, so we’re going to focus on our top five here.

Powell’s City of Books : The fact that we’re starting with an independent bookstore – the largest in the world, no less – tells you just about everything you need to know about Portland. It’s right in the heart of downtown Portland, and is an astounding collection of books from all genres. This place is amazing, and even since we’ve lived here I can’t walk out of here without at least one book. I bought a light blue Powell’s Books t-shirt on clearance almost a decade ago that I wear often, and every time I wear it outside of Portland (usually in Seattle) at least one person stops me to chat about how much they love Powell’s. They have an extensive collection of books, including big sections dedicated to fantasy/sci-fi, Pacific Northwest history, and graphic novels. We especially like the staff picks section in the entryway, which is a nice way to see what the staff are reading and recommending at the moment. 

The International Rose Test Garden : Washington Park – which is the park where this rose garden is located – is the best park in Portland, and is home to a bunch of different attractions including the Oregon Zoo and the Portland Japanese Garden. But the Rose Garden, which is both free and spectacular, is the best of the bunch, we think. There are 10,000 roses here, and when they’re in full bloom between roughly May and September (sometimes longer), it’s quite a sight to behold. 

Breakfast / Brunch in Portland: Portland is an excellent food city in general, especially when you consider prices are going to be about 25% lower than other cities on the west coast. However, it really shines in the morning, when you’ll find some world-class breakfast and brunch options. 

Now, you might expect to see Voodoo Donuts on this list. The novelty donuts are fun, yes, but it’s far from undiscovered, and there are honestly much better doughnuts to be had in Portland.

Like, a lot of them.

Go to Blue Star , Doe Donuts , Coco Donuts , or Petunia’s Pies and Pastries (for gluten free and vegan donuts) if you’re in and around Downtown Portland. 

Here are some of our favorites, in no particular order. 

• Fried Egg I’m in Love : Award-winning breakfast sandwiches! They have a food cart in downtown Portland, along with a brick & mortar shop on Hawthorne Blvd in Southeast Portland and up on Mississippi Avenue.
• Ken’s Bakery : The best bakery in Portland, probably. It’s in northwest Portland, and is a local favorite with a rotating selection of pastries that you can see them making right behind the register. Good sandwiches for lunch, too, but the hero is the pastries in the morning.
• Pip’s Original Doughnuts & Chai : Go for the mini donuts (they are NOT donut holes, Matt!) with innovative flavors, stay for the incredible chai. There’s a perpetual line, especially on weekends, so go when they open if you can. Alysha LOVES their chai (get a chai flight!). 

Explore The Eastside: While most of the tourist attractions like Powell’s and the Rose Garden (though Powell’s has a location on Hawthorne) are on the west side of the river, we actually like the east side of the river more. We’d divide this large and sprawling area into three distinct areas. If you’re staying downtown and don’t have a car, your best bets are going to be:

• The Central Eastside: Just over the river from downtown, this area is an old industrial district that has become a great place to spend an afternoon, with all sorts of places to eat and drink. We like Schilling Cider House (for 50 taps of different ciders), Cascade Barrel House (for beer), and the Revolution Hall Rooftop for drinks with panoramic views of Portland and Mount Hood).
• Southeast Portland: Our neighborhood! Centered on Hawthorne Blvd and Division St, this stretch runs straight through a residential neighborhood and is full of places to eat and drink. Fried Egg I’m in Love (breakfast sandwiches), Cibo (pizza), Lauretta Jean’s (pies), Pinolo Gelato (gelato), Magna Kusina (Filipino), and Oma’s Hideaway (Malaysian / Singaporean food) are the spots we’d hit.
• Mississippi Avenue: Where we used to live! The stretch along Mississippi Avenue might be the most bang-for-your-buck in terms of the amount of bars and restaurants packed into a relatively short stretch. For food, Lovely’s Fifty-Fifty (of Chef’s Table fame), Kate’s Ice Cream (plant-based ice cream), and the food cart pod at Prost . For drinks, go to Interurban . For shopping, don’t miss the Meadow , a store that we go to far too often with salt, chocolate, and bitters.
• The Alberta Arts District: The furthest from downtown Portland, Alberta Street is one of the main corridors in northeast Portland. Similar to the other places on this list, it’s packed with great food, drinks, and coffee. For coffee, don’t miss Proud Mary (our top coffee shop in Portland for fun single-origin coffees). For food, go to Tin Shed Cafe for brunch, Zilla Sake for excellent sushi and sake, and Matt’s BBQ Tacos for…tacos. For drinks, The Bye and Bye for good drinks and vegan food, and Great Notion Brewing for beer (and the aforementioned Matt’s BBQ Tacos, which operates on their patio). 

For more on planning your time in Portland, we’d encourage you to head over and read our other Portland guides.

• How to Spend One (Amazing) Day in Portland (What to See, Eat, and Drink)
• How to Plan an Amazing 3 Day Portland Itinerary
• Where to Stay in Portland: A Guide for First Timers
• Hiking in Portland: A Complete Guide to 20+ Great Hikes
• Where to Find the Best Specialty Coffee in Portland

What to Add with More Time in Oregon

Like we’ve said time and time again, two weeks is not really enough time to see everything there is to see in Oregon. Here are a few more things to consider adding if you happen to have more time. 

Mount Hood (+1-3 Days)

Where to Stay at Mount Hood: There aren’t that many places to stay here, but you do want to be in or around Government Camp on the south slopes of the mountain. There’s a Best Western , a campground at Trillium Lake that we like, and a bunch of nice cabins in the woods to choose from. 

Mount Hood is our favorite hiking destination within a couple of hours of Portland. We fell in love with it on that first road trip that eventually led us to move here, and we go back there as often as we can. 

Matt is from Seattle, where the towering peak of Mount Rainier is a near constant reminder of the natural beauty that sits just outside of the sprawling city (and also a constant barometer of the weather – “is the mountain out?” is a common question to evaluate whether it’s a nice day in Seattle). 

Mount Hood plays the same role for Portland, and we often have a similar conversation around Portland around whether Hood is out. 

During the winter, Mount Hood is home to some of Oregon’s best skiing. Then, when the snow melts in the late summer, it turns into a veritable alpine wonderland, with wildflowers blooming, roaring waterfalls, and stunning vistas of Mount Hood around every bend in the trail. 

The part you’re going to want to focus on here is the area in and around Government Camp , on Mount Hood’s southern side. 

That’s where all the action is, though that’s not to say there aren’t worthwhile places to visit on other sides of the mountain. 

By focusing there, you’re also nicely positioned for the next stop on your itinerary, Hood River, where you’ll just hop back on Highway 26 and continue north to Oregon’s northern border. 

For more, read our guide to the best hikes at Mount Hood (because it’s really all about the hiking here, at least in the summer). 

Day Trip from Portland to Silver Falls State Park (+1 Day)

Silver Falls State Park is a hair over an hour south of Portland, and it’s home to one of our favorite hikes in the state – the incredible Trail of Ten Falls . Which, as you might imagine, features 10 waterfalls over the course of a relatively easy eight mile trail. 

If you want waterfalls – and especially if you’re here in the spring and early summer when the water is high – this is as close to a must-do as it gets. 

After your hike, you can meander through the eastern end of the Willamette Valley on your way back to Portland, stopping at Bauman’s and E.Z. Orchards for farms and cider (and apple cider donuts!). 

The tiny town of Silverton is a nice place to stop for lunch after the hike (or just wait until you get back to Portland and check off some other places there!).

If you do want to stay overnight, the campground at Silver Falls is really nice.

However, other than that, there’s really not a whole lot of places to stay nearby, and you’re probably better off making it a day trip and staying in Portland for another night. 

What to Do with Less Time in Oregon

With less time – 7 or 10 days in Oregon – we’d make some adjustments and be more focused with your time. 

With 5 days in Oregon, we’d go ahead and spend the entire time in Portland, doing day trips out to the Gorge, the Coast, and Silver Falls to fill your time (you’d want to rent a car for that trip).

With 7 days , we think you have time for a nice little loop that encompasses Portland and the mountains OR the coast, but probably not both.

If you absolutely have to see both, you could add a day on to do a day trip out to the coast (Cannon Beach or Astoria) or the Columbia River Gorge (Hood River).

With 10 days , you have enough time to comfortably do a figure-8 that includes the mountains (Hood River and Mount Hood) and the coast (Cannon Beach and Astoria). 

Here’s a day-by-day breakdown of what those itineraries might look like. 

10 Days in Oregon

With 10 days, do a loop starting and ending in Portland that takes you first out to the mountains (and the Gorge), then head west to the coast for a couple of nights before returning to Portland. 

• Day 1: Arrive in Portland, drive to Hood River
• Day 2: The Columbia River Gorge
• Day 3: Hood River & Around
• Day 4: Mount Hood
• Day 5: Mount Hood
• Day 6: Drive to Cannon Beach
• Day 7: Cannon Beach & Around
• Day 8: Tillamook & Three Capes Scenic Loop
• Day 9: Drive to Portland
• Day 10: Portland & Fly Home

7 Days in Oregon: The Mountains

Here’s what a perfect 7 days in Oregon might look like, focused on the northwest corner of the state around Portland. 

Add a day if you want to do a day trip out to the coast (and read our guide to the best day trips from Portland ).

• Day 6: Portland
• Day 7: Portland & Fly Home

7 Days in Oregon: The Coast

Add a day if you want to do a day trip out to the mountains, and focus on Hood River or Mount Hood. 

• Day 1: Arrive in Portland, drive to Astoria
• Day 2: Astoria
• Day 3: Cannon Beach & Around
• Day 4: Tillamook & Three Capes Scenic Loop
• Day 5: Drive to Portland

For more on this particular version of the trip, we’d read our guide to planning an Oregon Coast Road Trip , which has TONS of detail.

Matt is the founder and main writer behind Wheatless Wanderlust, which he started back in 2018 as a way to share his gluten free travel guides with his fellow Celiac travelers.

Since then, Matt and his wife Alysha have visited 18 national parks, spent three months in Europe and six weeks in Colombia, and have explored every corner of the Pacific Northwest, which is where Matt grew up.

He writes super detailed guides to the places they visit, bringing together personal experience and historical context to help YOU plan an amazing trip.

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The Perfect 10 Day Oregon Road Trip Itinerary

Years ago, when I lived in Texas, I decided to visit the beautiful state of Oregon. Since I love exploring mountains and beaches, I decided to make the most of it and do an ultimate Oregon road trip! I fell in love with this state and all that it has to offer, and it was one of the many reasons I moved to the Pacific Northwest. Now I visit this excellent state at least twice a year. I mean, it is so dang close to me now! So I wanted to make it easy for you and highlight my favorite things to do there! Hikes, restaurants, viewpoints, etc. I hope you love Oregon as much as I do after your trip.

Disclosure: This post contains affiliate links. If you click one of them, I may receive a small commission (for which I am very grateful for) at no extra cost to you. 

Download my free Outdoor Photography Guide

Oregon road trip map.

Below is a screenshot of the route and a Google map you can download and use throughout your trip.

Oregon Road Trip

Day 1 – portland.

What I loved most about Portland was the food! OMG, everywhere that I ate, I was mesmerized. We even found one of the spiciest dishes of our life, and we love spicy food. Some popular things include:

• Drinking a beer at Deschutes Brewery
• Visiting Powell’s Bookstore
• Eat At Voodoo Doughnut for breakfast
• Checking out the International Rose Test Garden
• Check out the Portland Japenese Garden

>>> Book A Portland Tour Here

Where To Stay In Portland

• The Mark Spencer Hotel : An excellent hotel a few minutes away from Powell’s Bookstore and the Japenese Garden. >>>Book Here

Day 2 – Columbia River Gorge

Hikes and viewpoints.

I am in LOVE with the Columbia River Gorge. I go to this area at least once a year now. I am captivated by all the waterfalls, the views of Mount Hood, the wineries, restaurants, and farms. It is such a fun area, and it is the number one thing to do in Oregon. If someone told me there was only one area I had to pick to explore, it would be this one.

The number one thing to do in the Columbia River Gorge is to chase waterfalls. There is a road called the Historic Columbia River Highway, and there are many waterfalls here! Some popular ones include Latourell Falls, Bridal Veil Falls, Wahkeena Falls, Fairy Falls, Multnomah Falls, Horsetail Falls, Ponytail Falls, and Dry Creek Falls.

Read More: The Ultimate Columbia River Gorge Waterfalls Road Trip

You can also hike around the gorge to get a better viewpoint of the Columbia River. I loved wandering the Mosier Plateau Trail during the spring, as the flowers are all out.

Food And Drinks

Unwinding after some waterfall chasing around the Hood River Waterfront Park is a must. This place is so stunning and relaxing! We grabbed some pizza at Solstice Wood Fire Pizza – Cafe & Bar and took it to the park. It was a beautiful sunny day, and we watched people kayak the Columbia river.

I also loved eating at the Riverside restaurant for brunch and loved Garnier Vineyards as well as the Mt. Hood Winery .

If you want to go kayaking or windsurfing, you can rent it at Big Winds. This is a popular thing to do in the summer in Oregon .

Where To Stay In Hood River (Stay Here For Two Nights)

Hood River Hotel:  Hood River Hotel is the oldest hotel in Hood River, Oregon, and has been updated with a cute modern style. There is a restaurant on-site, and it is pet-friendly. >>>Book Here

Day 3 – Mt. Hood

Mount Hood is such a perfect place to visit in the summer. The mountain is stunning, and there are so many fun things to do outdoors!

I am such a sucker for good fruit! I love visiting local farms, and Mt. Hood has a ton of them. My favorite farm was Kiyokawa Family Orchards, as you can pick your fruit, and it has such a fantastic view of Mount Hood. If you want a map of all the farms in the area, click here .

Great Hikes

• Tom Dick and Harry Trail: Great views of Mirror Lake and Mount Hood and labeled as hard.
• Trillium Lake Loop: Easy trail and great if you want an epic photo of Mount Hood with a lake.
• Tamanawas Falls: Moderate waterfall hike on the east side of the mountain.
• Ramona Falls : Another excellent waterfall hike.

Day 4 – Silver Falls State Park

Read More: Trail of Ten Falls, Oregon Guide | Silver Falls State Park

Trail Of Ten Falls

Silver Falls State Park is one of the most underrated state parks I have ever seen. This park is outstanding, and there are so many waterfalls here! Around 10 of them, and they are all epic. When I heard about this place, I thought one or two waterfalls would be beautiful and the rest would be mediocre, but nope! They were all fantastic and stunning.

The main trail is called the “ Trail of Ten Falls ,”. It is 7.4 miles round trip with an elevation gain of 1,200 ft and is rated moderate. When I did the hike, it was closer to 8 miles. This is pretty much an all-day adventure, so pack your hiking equipment and drive to this lovely park. Parking at Silver Falls is $5 per vehicle.

Where To Stay In Salem

• Hotel Hampton Inn and Suites Salem: >>>Book Here Now

Day 5 – Bend

Take a hike.

Some popular hikes in the area include South Sister Summit , and Green Lakes Trail . I will tell you about my all-time favorite waterfall hike, which is a little out of the way from Bend (an hour and a half). It is Proxy Falls, and it is shown below. It is only 1.6 miles with an elevation gain of 147 ft. and I highly recommend it! Get up early in the morning and hike this trail, then drive to Bend, relax and enjoy the rest of your evening :-).

Visit A Brewery

I have been to Oregon many times, and something I have regretted in the past was not spending enough time in Bend. This town is so much fun! It is hip and filled with food trucks, breweries, and wineries.

Read More: Amazing Things to Do in Bend, Oregon | 20 Top Activities & Attractions

Bend is known for its breweries, so you have to visit at least one of them! Most have food, so it is still fun to visit even if you aren’t a beer person. Some of the popular ones include:

Where To Stay In Bend (Stay Here For Two Nights)

• Hotel SpringHill Suites by Marriott Bend: We stayed at this hotel, and I loved it. It was clean, close to many restaurants, breweries, and had a nice bar. >>>Book Here

Read More: Where to Stay in Bend, Oregon | 7 Top Hotels & Hidden Lodgings

Grab Your Free Car Camping Checklist! 🚗🌲

Ready to elevate your car camping game? Snag our essential checklist to ensure you’ve got everything you need for a stress-free, fun-filled adventure! Perfect for beginners and seasoned campers alike. Download now and hit the road prepared! 🌟🎒

Day 6 – Smith Rock State Park And Painted Hills

Painted hills.

When I explored Oregon for the first time, I was surprised at how much the landscape changed after driving only a few hours. You can go from lush green forests to a desert in a mere few hours. An entertaining and different area to explore is Painted Hills . It is located in Eastern Oregon and is a combination of many hills with red, yellow colors swirling around. You can’t get too close to the red-yellow area, but the Painted Cove Trail features close-up views of the red formations.

Out of everything I experienced in Oregon, this is probably my least favorite thing on this list. So if you are limited on time and don’t want to make the drive here, you can skip it and do an activity much closer.

Pro Tip: Fill up on gas before heading out to Painted Hills as there is not much around there.

After exploring Painted hills in the morning, head out to Smith Rock for sunset. You can hike around this stunning place and do trails like Painted Cove Trail, Misery Ridge, and River Trail , or the Rim Rock trail. You can also rock climb Smith Rock which is what we did and it was a blast!

Read More: The Ultimate Guide To Smith Rock Hiking Trails

Day 7 – Umpqua National Forest

Toketee falls.

If you want something that is more bang for your buck, then check out Toketee Falls ! This waterfall hike is only 0.9 miles with a 167 ft elevation gain. I loved this trail! It was so easy to do, and the trees are lush and green.

Umpqua Hot Springs

One of the most popular hot springs in Oregon is the beautiful Umpqua Hot Springs . There are around eight pools that can fit about 2-4 people. The trail is approximately 0.8 miles round trip with an elevation gain of 305 ft. The hot springs are only open from sunrise to sunset, so you cannot camp there overnight. Also, the parking lot only holds ten cars, so get there early!

I also want to say that this area is known to be constantly trashed. Please pick up after yourself and don’t leave any items behind. That includes food (seeds and banana peels), and beer cans.

Watson Falls

Watson Falls is another easy trail that has a magnificent waterfall viewpoint. The trail is only 1 mile long with an elevation gain of 524 ft. It is relatively close to Toketee Falls, so make sure you check this waterfall out!

Diamond Lake

Diamond Lake is a great place to stop if you want a great mountain view with a lake. Here you can have a perfect view of Mt Bailey with Diamond lake in the foreground.

Where To Stay Near Crater Lake (Stay Here Two Nights)

• Crater Lake Lodge: One of the few hotels located in the National Park. >>>Book Here

Read More: Where to Stay Near Crater Lake National Park | Lodging & More

Day 8 – Crater Lake National Park

I dream of revisiting Crater Lake National Park! This place is a gem. I almost took this out of our itinerary years ago, and I am so thankful my husband told me to include it. My jaw dropped when I saw it. I had never seen such a dark, sapphire-blue lake in my life. It is known to be the deepest lake in the United States!

Read More: 14 Best Things To Do at Crater Lake National Park

Things to Do At Crater Lake

• Go to some of the viewpoints: The best ones are Watchman Overlook, Phantom Ship Overlook, and Cloudcap Overlook.
• Drive Around: You can drive around the whole lake to take in its beauty.
• Hike and Swim: There is only one way to swim in the lake and that is by hiking the Cleetwood Cove Trail . We did this, and it was so fun but freezing! Even on the hottest day, the water was chilling.

Day 9 – Samuel H. Boardman State Scenic Corridor

Samuel H. Boardman State Scenic Corridor is located on the southern coast of Oregon. It has become one of the most popular Instagram spots in Oregon, and for a good reason. The area is filled with cliffs and waves crashing into them and sea stacks filled with evergreen trees. It is breathtaking!

Most viewpoints are pretty easy to get to, making it a perfect spot to relax or take pictures. No extensive crazy hiking is needed to get these views. Popular viewpoints include the Whaleshead Beach, Cape Ferrelo viewpoint, House Rock Viewpoint, and Indian Sands Viewpoint.

The most popular area is the Natural Bridges which is best to see for sunrise. This area can be a bit difficult to get to. At the parking lot take a right (if you are facing the beach). Then take two lefts when you get to the junctions. The trail is very steep so bring good hiking shoes.

Want To Learn More On Samuel H. Boardman : Check Out My Post On The Best Oregon Coast Road Trip

Where To Stay Near Samuel H. Boardman

Tu Tu’ Tun   Lodge (Gold Beach):  This place is fantastic and nestled in a beautiful forest area. >>>Check It Out Here

Day 10 – North And Central Coast

Exploring the Oregon Coast is a must on your Oregon road trip! There are many cute coastal towns like Cannon Beach (my fav)! If you want to extend your trip to be a bit longer than ten days, then stay a few days on the coast. There is so much to see and to do here.

Some of my favorite stops on the coast include:

There is so much more to do than what I listed above. Those are just a couple of my favorite areas. I do feel like you need more than one day to explore the central and northern coast. But if you are limited on time, I would only stop at Cape Kiwanda and Cannon Beach. Cannon Beach is the cutest town and has many hotels and yummy restaurants.

Want To Learn More On The North And Central Coast : Check Out My Post On The Oregon Coast

Where To Stay In Cannon Beach

Surfsand Resort(Cannon Beach):  This is where we stayed the first time we came to Cannon Beach. They have oceanfront rooms and a heated indoor swimming pool and hot tub. I enjoyed our stay here, and I loved that we could walk easily to the beach.   >>>Check It Out Here

Day 11 – Go Home

Such a sad day! Going home is hard. Oregon has some of the most epic sceneries in the country. When I first came to Oregon, I vowed to come back, and what do you know, I moved to the state right next to it. I now visit Oregon at least twice a year, and every time I am still amazed by its beauty.

What To Pack When You Travel In Oregon

• Sunscreen:  Super important and it is part of the ten essentials!   >Buy Sunscreen
• Chapstick:  This one has SPF so your lips won’t get burned!  >Check Out This Chapstick
• Hiking Boots/Shoes:  If you use tennis shoes, you can easily hurt your toes hitting a rock by accident (Trust me, I have done it so many times before).  >Check Out My Hiking Shoes
• Hiking socks:  Having the correct socks helps you prevent getting blisters. Smart Wool is probably my favorite brand out there.   >Buy Hiking Socks
• Water Reservoir:  Water reservoirs help prevent me from getting dehydrated while hiking. The great thing about this reservoir is that it doesn’t have the plastic taste.  >Here Is My Water Reservoir
• Water:  Stay nice and hydrated.
• Sunglasses:  It can get sunny, so make sure to pack some sunglasses.  >Check Out These Sunglasses
• Snacks:  The best snacks are jerky, nuts, and energy bars.  >>>Love These Snacks Here
• Camera:  The Sony A6000 was one of the first cameras I started traveling with. The Sony A6000 is an excellent camera for people that want to start improving at travel photography.    >Buy Sony Camera Here
• First Aid Kit:  This is one of the first things I bought when I first started going on adventures. It is super portable.  >Buy This Awesome First Aid Kit Here
• Day Pack to carry all your things:  To carry all your gear, water, and food, you need a good backpack. Osprey is known to have some of the best backpacks in the market.  >Buy This Great Quality Backpack
• Headlamp:  A headlamp is an absolute must in case you get stranded in the dark! It is a lot more portable and easier to use than a flashlight.  >Buy A Headlamp Now
• Leggings or Hiking Pants:  I always wear leggings while hiking because it is what I feel most comfortable with!  >Click For My Favorite Hiking Leggings
• Breathable sweat-wicking shirts : Cotton shirts soak up your sweat when hiking, so make sure to wear something breathable.  >Check out this awesome breathable shirt here.
• Mid Base Layer:  It can get chilly in Oregon even in the summer.  >Check Out My Sweater Here
• Sports Bra:  For women.  >Check This One Here
• Jacket:  I always have a jacket in my backpack, even if it is hot. I do it just in case of an emergency.   >Buy My Favorite Jacket
• Rain Jacket:  The worst feeling in the world is being wet and cold while hiking. You can get hypothermia, so always carry a poncho or a rain jacket when you hike Oregon.  >Check Out My Rain Jacket Here
• Tripod:  This is an optional item, but it is excellent for getting the ideal sunset pictures.  >Check out this tripod
• Knife:  I always carry a knife in my backpack just in case.  >Check Out My Knife Here

Claim your FREE Hiking Checklist

Ready to start hiking? Grab my free hiking checklist and never forget anything at home!

7 Day Oregon Itinerary

If 10 days is too long, then I have made a smaller 7 day Oregon road trip. I have only listed my seven favorite spots.

4 Day Oregon Road Trip

Final thoughts on best oregon road trips.

Thanks for reading about road trips in Oregon! If you need other PNW inspiration, make sure to check out my other blog posts:

• The Ultimate Pacific Northwest Road Trip Itinerary
• Best Hikes In Washington State
• 25 Amazing Oregon Waterfalls You Need To See Today
• The Ultimate Columbia River Gorge Waterfalls Road Trip
• The Best Things To Do On The Oregon Coast
• 16 Fun Things To Do In Astoria Oregon

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Bucket-List Oregon Road Trip Itinerary

March 15, 2024 //  by  Follow Me Away //   45 Comments

Planning the perfect Oregon road trip itinerary doesn’t have to be stressful or overwhelming!

Oregon has so much to offer including lively cities, great wineries, a gorgeous coastline, amazing waterfalls, and stunning mountains.

I love to road trip Oregon and have explored the state from top to bottom. I have yet to be disappointed by a single place! If you are planning a trip to Oregon, I am here to help!

Highlights of this road trip planner for Oregon include:

• Multnomah Falls
• Willamette Valley Wineries
• Oregon Caves National Monument
• Samuel H. Boardman State Scenic Corridor
• Cannon Beach

My Oregon example itinerary is written in a clockwise manner around the state, beginning and ending in the Portland area. Feel free to modify it for your interests and do it on your own schedule.

Don’t forget to check out my detailed road trip packing list so you don’t forget any essentials!

Get ready to plan the best Oregon vacation itinerary!

Oregon Road Trip Map

To save you some time, I created this Oregon road trip map. Click the link below and plug the map into your GPS.

Sometimes having a visual of where you are going is very helpful when planning a road trip!

This Oregon road trip map will help you plan your stops and get an idea of where they are located.

Click Here For Oregon Road Trip Map

Start Your Oregon Road Trip By Flying Into Portland

Portland is the largest city in Oregon and also the most accessible to fly into to begin your Oregon road trip.

Both affordable international and domestic flights fly into Portland. I recommend  checking out Skyscanner to find the best and most affordable flights. You can easily compare rates.

Alternatively, if you have a shorter amount of time, I recommend flying into Eugene, Oregon.

Eugene is centrally located so you can do either the top or bottom half of the state more easily, depending on your schedule and desires. Flying into Eugene can be more expensive than Portland, however.

After landing in whichever airport you choose, you can pick up your rental vehicle and hit the road!

Stop 1: Portland And The Columbia River Gorge

In case you didn’t know, the motto of the city is “Keep Portland Weird” so you really want to stop in Portland for at least a day to check it out before you begin your Oregon road trip.

I stayed in Portland for 4 days and used it as a base to explore the nearby Columbia River Gorge but you can choose to fly in, see the city, and then head out to nature if you prefer.

There is so much to see and do in Portland !

I recommend visiting the world-famous Japanese Garden which will transport you to another culture. Washington Park is another great stop as well if you love the outdoors.

Where Portland really shines is the food scene. During your time in the city, check out some of the food carts! They have drawn international acclaim and once you take a bite, it is easy to see why!

From sweets and crepes to pho and comfort food, the food carts in Portland will not let you down!

If you have never checked out Voodoo Doughnut, it is a bit touristy but a classic! I promise you it is delicious and worth the wait.

Book Here: City of Portland Tour: Historic and Iconic Sights

Book Here: Portland: All-Inclusive Walking Food Tour

The Columbia River Gorge is a magical stretch of land about 45 minutes away from Portland! To explore it, you can either camp nearby, stay in Portland, or stay in the nearby town of Cascade Locks.

The Columbia River Gorge is filled with beautiful waterfalls and hikes, making it one of the top Oregon travel destinations!

Best Columbia River Gorge Road Trip Stops

Multnomah Falls. Multnomah Falls is an Oregon itinerary classic! You’ve probably seen at least one photo of this popular waterfall!

Multnomah Falls is the most popular stop in the Columbia River Gorge area and it is easily accessible from the road. Walk to the base of the falls or take a short hike and cross over the iconic bridge.

I recommend taking the short hike as the view from the bridge is beautiful!

Latourell Falls. I love Latourell Falls because you can see basalt columns up close and personal.

This is the closest waterfall to Portland and makes a great first stop on your Oregon road trip.

There is a Latourell Falls hike that is 2 miles, but you only have to walk a few feet from the parking lot to see the actual waterfall so don’t let the hiking distance put you off!

Wachella Falls. I highly recommend a visit to this beautiful waterfall!

Wachella Falls is an easy 2.4-mile round-trip hike. It is perfect for families or people who don’t want to hike super far for a great payoff!

Wachella Falls is a great afternoon hike and the shade from the gorge protects you from the sun if it is a hot day. Pack a picnic lunch!

Book Here: From Portland: Columbia Gorge Waterfalls Tour

Recommended Time To Spend

Set aside at least one day to explore Portland if you are looking for a city atmosphere.

Depending on what you want to do in the Columbia River Gorge, I recommend spending 1-2 days exploring the area especially if you want to do a lot of hiking.

If you are on a limited schedule, you can do the Columbia River Gorge area in one day on your out of Portland. Start your day early so you have enough time to see everything.

Best Hotels In Portland :

• The Nines, a Luxury Collection Hotel . Check Rates: Booking.com
• Bluebird Guesthouse . Check Rates: Booking.com

Stop 2: Mount Hood

Mount Hood is the most famous mountain in Oregon and is actually a volcano! This is such a unique stop on a road trip in Oregon.

Mount Hood is located a little over 2 hours away from Portland and you will pass through the Columbia River Gorge on your way there.

One of my favorite views of Mount Hood is from Trillium Lake. This lake is very easily accessible and a great spot to watch the sunset or to shoot astrophotography.

If you want to do more hiking, Lost Lake provides a similar view to Trillium Lake but takes more effort to get to.

Mount Hood is the perfect stop on your eastern Oregon itinerary if you love adventure and the outdoors!

You can drive up Mount Hood itself and there is a lodge at the top. If you are planning the best trip to Oregon during the winter or fall, Mount Hood may have snow and the peak is open for skiing!

In the summer, many of the best hikes in Oregon start from the lodge on top of the mountain.

Book Here: Portland: Mt. Hood Day Tour

We recommend spending at least one night exploring the Mount Hood area. Mount Hood is centrally located between the Columbia River Gorge and Bend, your next stop, so if you just have to catch it as you pass by, that is okay too!

At a minimum, you should try and visit Trillium Lake for some wonderful mountain views as it is one of the nicest places to see in Oregon!

Best Hotels Near Mount Hood:

• Located On Mount Hood: Timberline Lodge . Check Rates: Booking.com
• Beautiful, Modern Lodge: Cooper Spur Mountain Resort . Check Rates: Booking.com

Stop 3: Painted Hills And Smith Rock

Did you think you would see the desert during your Oregon road trip? The Oregon Desert takes up most of the state. It just doesn’t get much love when people are looking for places to visit in Oregon.

I recommend getting an early start as the Painted Hills are a bit out of the way and it takes about three hours to reach them from the Mount Hood area.

The Painted Hills are unique and in a very rural area of Oregon, so I highly recommend ensuring your gas tank is completely full before venturing out.

When visiting the Painted Hills in Oregon, I suggest doing the Painted Cove Trail and the Painted Hills Overlook. The Painted Hills are nice just to drive around if you don’t want to do any of the walks.

This is the desert so if you visit Oregon during the summer, bring extra sun protection and lots of water!

Finally, don’t ever step off the approved trail as these locations are very fragile and even one set of footprints will ruin the landscape.

If you need to save time on your Oregon itinerary you can skip the Painted Hills and head straight to Smith Rock.

If you have never heard of Smith Rock State Park , you are in for a real treat! This is the true desert on your eastern Oregon road trip. It is a hiker and rock climber’s paradise!

I recommend visiting either during sunrise or sunset if you want to beat the heat. Smith Rock is one of the best places to see in the state. Make sure it tops your road trip to Oregon!

Smith Rock State Park is located just 40 minutes from the adorable city of Bend, Oregon, and about 1 hour from the Painted Hills so it is easy to do both in one day.

That said, many serious hikers and climbers choose to spend multiple days exploring Smith Rock State Park during their Oregon trips.

If you aren’t a big hiker, simply visiting Smith Rock and walking around will be enough. Believe it or not, “the view” is accessible right from the parking lot so you don’t have to go on a long hike.

I was honestly surprised that the more famous view could be seen right from the parking lot and pleased about it too!

If you are looking for a hike, the Misery Ridge Hike is a popular choice. It is quite steep and strenuous so wear proper hiking gear.

This hike will take you to the top of Smith Rock for memorable views as far as the eye can see.

When you are done exploring the area, I recommend spending the night in Bend, Oregon! You will love the brewpub culture, delicious food, and cute downtown!

I recommend at least one full day exploring the Painted Hills and Smith Rock State Park. They can both be completed in a day if you leave early.

If you have more time or want to do more hiking and climbing, then you can stay two days in the area.

Best Hotels Near Bend, Oregon:

• Classic: DoubleTree By Hilton Bend . Check Rates: Booking.com
• Budget: Cascade Lodge . Check Rates: Booking.com

Stop 4: Oregon Waterfalls And Hot Springs Near Eugene

After Bend, you will head through a stunningly rugged mountain pass that is now a lava field as far as the eye can see. This is a great photo opportunity as lava fields aren’t common in the United States!

Once you cross through the lava field, you will pass from the desert into a beautiful lush forest. This is one of my favorite parts of this Oregon itinerary and you are going to love it!

Proxy Falls

As you descend the mountain pass, you will enter the forest that is home to the stunning Proxy Falls! This is my favorite waterfall on this itinerary for Oregon!

This waterfall is breathtaking in person and you really can’t tell how large it is until you get up close!

Proxy Falls Loop Trail is a well-trafficked, 1.6-mile trail. It is well-marked and I consider it easy. It winds through a beautiful forest and down along a mossy lava field before you arrive at Proxy Falls.

I recommend taking the trail to Lower Proxy Falls which will bring you to the base. Be warned: the final hike down to Lower Proxy Falls is quite steep and may not be accessible for everyone.

If you can’t hike all the way to the base, there are a few lovely viewpoints where you can see the entire falls without the steep downhill hike.

Sahalie And Koosah Falls

After Proxy Falls, continue to Sahalie Falls and Koosah Falls. These waterfalls are located along the crystal-blue McKenzie River and are some of the best waterfalls in Oregon !

Both Sahalie and Koosah Falls are very easily accessible from the parking lot and there is virtually no hike at all to see these stunning waterfalls!

Sahalie Falls thunders down over a ledge and Koosah Falls ends in a perfectly blue pool of water.

Don’t skip these waterfalls because you can see them quickly and be on your way. Both of these waterfalls make noteworthy stops on an Oregon road trip!

Make sure to check road closures before heading out to these waterfalls.

Tamolitch Blue Pool

Tamolitch Blue Pool is one of the best places to visit in Oregon if you are looking for something unique during your trip!

This fascinating water feature is located along the McKenzie River Trail! This pool is crystal clear to the point that it appears to only be a few feet deep. In reality, it is closer to 30-40 feet deep!

Tamolitch Blue Pool is marked as one of the best swimming holes in the world, but this is false and you should beware! The water here, although beautiful, is extremely cold, in the 30s, and is not meant for swimming.

The forest service regularly has to save people who have jumped in and been shocked by the cold water.

Plus, swimming in Tamolitch Blue Pool will ruin it because of the oils on your clothes and skin as well as your makeup or sunscreen.

When visiting, I urge you to look with your eyes and not jump in the water for both your sake and the environment.

Terwilliger Hot Springs

Since I am on a “blue” theme, Terwilliger Hot Springs is an interesting addition to your itinerary.

These Oregon hot springs are tucked away in the mountains in the McKenzie River area and look like something out of a storybook.

They are clear, blue pools heated by the lava underneath the volcanic mountain, and you have a view of the forest while you soak. There are also multiple pools with varying temperatures.

Keep in mind that nudity is allowed at Terwilliger Hot Springs and if you decide to make this a stop, you need to be prepared.

You can wear swimsuits as I did, but other bathers may not so you need to make sure to be respectful.

There are even families with kids at Terwilliger Hot Springs, despite it being a nude hot spring .

Visit Eugene For Brew And Foodie Culture

You will spend the night in Eugene, Oregon, which is the hub of central Oregon.

There are so many delicious places to eat in Eugene, and I particularly love the 5th Street Public Market. It is a unique little area with shops and dining.

Eugene is a college town so there may be a college football game during your stay. This is a very busy time for Eugene so be sure to plan ahead as lodging options can fill up quickly.

I highly recommend spending at least 1 night in Eugene and giving the entire McKenzie River area 2 full days to explore.

You may want to use Eugene as a “base” to explore the next two stops or continue and stay in the heart of each future stop. Since the next two stops are nearby, Eugene may have affordable lodging options.

Best Hotels Near Eugene: 

• Mid-Range: Downtown Inn . Check Rates: Booking.com
• Luxury in Downtown: Graduate Eugene . Check Rates: Booking.com

Stop 5: Wine In The Willamette Valley

If you love wine, you are going to  love the  Willamette Valley ! It is home to over 500 wineries and is second only to Napa Valley in the United States for the production of wine.

Sounds crazy, right? I thought so too until I saw what a Willamette Valley winery looked like!

The Willamette Valley is 150 miles long and you can either stay in a local bed and breakfast in the valley or use Eugene as your base.

I visited King Estate Winery and was majorly impressed! King Estate Winery is like being in Tuscany, Italy! The landscaping, the vineyards, and the huge manor house all come together to transport you to Italy!

If you are into wine, you can spend a good portion of your Oregon road trip sipping wine and eating cheese and crackers.

Book Here: Willamette Valley Wine Tour

If you want to experience the Willamette Valley on your Oregon road trip and aren’t hugely into wine, you can spend a morning or afternoon exploring the wineries.

If you are a big wine fan, you could easily spend 1-2 full days in the Willamette Valley wine region because there is so much to see and do!

You may even want to skip this stop altogether if wine isn’t your thing.

Where To Stay In The Willamette Valley:

• Beautiful B&B: LANZAROTTA Bed and Breakfast . Check Rates: Booking.com

Stop 6: Covered Bridges In Cottage Grove

Cottage Grove is a hidden gem along your Oregon trip, and I highly recommend visiting the little town. It is located less than 45 minutes from Eugene. If you want to pop over for a day trip, it is easily accessible.

If you think covered bridges are boring, you are mistaken! They are super fun and a unique piece of history. Plus, Oregon is home to the most covered bridges west of the Mississippi!

Cottage Grove is home to a covered bridge trail. You can choose to either drive or take a bike along the road and visit them all. I recommend driving and getting out at each covered bridge.

There are covered bridges located right in the heart of Cottage Grove and others that you need to see by driving a bit outside of town. You will love all these covered bridges in Oregon !

While in the Cottage Grove area, you can get off the beaten path and visit some lesser-known waterfalls once you are done hunting covered bridges.

Pinard Falls, Spirit Falls, and Moon Falls are all located within 45 minutes of Cottage Grove.

Each waterfall is located down a small dirt road high in the Umpqua Forest and requires a short and steep moderate downhill hike to get to. Find more info about waterfall wandering in Cottage Grove !

Cottage Grove is definetly a great hidden gem for the best Oregon road trips!

I suggest spending at least 1 day exploring Cottage Grove during your trip to Oregon!

If hidden waterfalls and covered bridges don’t sound interesting, you can skip Cottage Grove. But if you want to explore the area, you are going to need at least one full day to do it justice!

Where To Stay In Cottage Grove Oregon:

• Mid-Range with a Pool: Best Western Cottage Grove Inn . Check Rates: Booking.com
• Mid-Range: Cottage Grove Inn . Check Rates: Booking.com

Stop 7: Oregon Caves National Monument

Did you know there are caves in Oregon? The Oregon Caves are the most detailed cave system west of the Mississippi and something you shouldn’t miss.

The caves can be accessed from the small town of Cave Junction along highway 199. Once you turn off the road, it is quite a long and winding drive up to the Oregon Caves.

Keep in mind that the caves are cold and damp so dress appropriately. If you don’t have warm clothes, the Ranger Center has free jackets you can wear when exploring the caves. 

This is a great stop if you are traveling with kids as they love the caves and there are lots of programs including Junior Ranger programs and Ranger-led walks.

I suggest spending between 1-3 hours exploring the Oregon Caves! That should be enough time to visit the caves and enjoy the Visitor Center. 

Where To Stay In Grant’s Pass [Closest City To Oregon Caves]:

• Mid-Range: The Lodge At Riverside . Check Rates: Booking.com
• Beautifu Hotel with Pool: Redwood Hyperion Suites . Check Rates: Booking.com

Stop 8: Samuel H. Boardman State Scenic Corridor  

The  Samuel H. Boardman State Scenic Corridor is my absolute favorite part of this Oregon road trip guide! I love this little slice of the Oregon coast and it is essentially a mini-road trip in itself.

There are over eleven awesome stops here and each one has something unique to offer.

My favorite part is Natural Bridges and Secret Beach. I have been back to each of these places multiple times and each time I am stunned at the beauty and scale of each.

If you want to find the top viewpoints at Natural Bridges, check out my article on the best photography locations in Oregon .

If you want to focus more on the Oregon coastline, I also have a detailed Oregon coast road trip itinerary .

Best Samuel H. Boardman State Scenic Corridor Stops :

• Arch Rock (Mile 344.8) 
• Secret Beach (Between Mile Marker 344-345)
• Spruce Island (Mile 345.0)
• Thunder Rock Cove (Mile 345.8)
• Natural Bridges (Mile 346.0)
• North Island (Mile 347.4)
• Thomas Creek Bridge (Mile 347.8)
• Indian Sands (Mile 348.6)
• Whaleshead Overlook (Mile 349.3)
• House Rock (Mile 351.2)
• Cape Ferrelo (Mile 351.9)
• Lone Ranch Picnic Area (Mile 352.6)

Some people head through the Samuel H. Boardman State Scenic Corridor in a single day. I personally think that is way too fast but if you are pressed for time, it is still 100% worth the stop.

If you want a more detailed experience, I recommend between 2-3 days here because there are so many hikes and stops.

I have even spent as long as 4-5 days here so you know that it is just a really fantastic stop when taking a trip along the Oregon coast.

Hotels Near Samuel H. Boardman:

• Affordable: Brookings Inn Resort . Check Rates: Booking.com
• Rental Home with Views: Whaleshead Ridge . Check Rates: Booking.com

Stop 9: Bandon And Florence Beaches

After you leave Samuel H. Boardman State Scenic Corridor located on the southern Oregon coast, you are going to visit some wonderful stops on the mid-southern coast.

This is a stunning part of the Oregon road trip itinerary and Bandon is my second favorite stop along the Oregon coast.

Bandon is such an underrated stop and the beach is everything you would hope for in a Pacific Northwest beach.

Bandon Beach is home to towering sea stacks, sea caves, tide pools, and walking trails. It offers so much to see and do!

If you can, make sure to go at low tide so you can walk into the sea caves. Just be sure to not stay out there too long because you don’t want to be stuck in rising water!

Seeing the sunset on the beach in Bandon is a must-do and I highly recommend it!

Where To Stay In Bandon:

• Mid-Range: La Kris Inn . Check Rates: Booking.com

Once you are done in Bandon, head to Florence which marks the middle point of the Oregon Coast. Florence is one of the quaint towns on the Oregon coast and really evokes a vintage flair.

Another unique location? The Oregon Sand Dunes is located just to the south of Florence! The Oregon Sand Dunes are so much fun landscape to explore.

Finally, make sure to stop at Thor’s Well , about 30 minutes north of Florence, either while you are staying in the town or while you proceed along to the northern Oregon coast. 

I recommend spending one day in Bandon and one day in Florence.

If you don’t have two days, then spend one night in Bandon and drive through Florence with stops at the Oregon Sand Dunes and Thor’s Well.

Where To Stay In Florence:

• On the Beach: Driftwood Shores Resort . Check Rates: Booking.com

Stop 10: Cape Kiwanda And Cannon Beach

Cape Kiwanda and Cannon Beach are a few hours away from each other and offer similar yet unique experiences.

Cape Kiwanda is famous for a huge sea stack that sits out in the water. Here, you can drive straight onto the beach when allowed and then walk along the sand dunes to explore and hike.

When you visit Cape Kiwanda, I suggest taking your shoes off and walking around in bare feet. If you hike in shoes, they will fill with sand and get bogged down making it uncomfortable and hard to walk.

Where To Stay In Cape Kiwanda:

• Mid-Range: Inn At Cape Kiwanda . Check Rates: Booking.com

Cannon Beach is 1.5 hours north of Cape Kiwanda and is the furthest north you will visit on this Oregon road trip.

Like Cape Kiwanda, Cannon Beach is home to a massive sea stack that sits right off the beach. Unlike Cape Kiwanda, the sea stack here is much closer to the beach so you can really feel the presence of the towering rock.

Almost all Oregon road trip itineraries include Cannon Beach because it is so famous!

I highly recommend adding both of these stops to Oregon driving routes as both beaches are so pretty!

Book Here: From Portland: Oregon Coast Day Trip Cannon Beach Area

I suggest spending a few hours in Cape Kiwanda and then spending the night at Cannon Beach. If you want to do serious hiking at Cape Kiwanda, then schedule more time here.

If you start early, you should have enough time to hit both Cape Kiwanda and Cannon Beach all in one day.

Cannon Beach is a very popular seaside town so it is a great way to end your Oregon road trip with a walk along the beach and some relaxation before flying home.

Where To Stay At Cannon Beach:

• Great Views: Inn At Haystack Rock . Check Rates: Booking.com
• Affordable: Ocean Front Motel . Check Rates: Booking.com

End Your Oregon Road Trip In Portland 

Once you finish exploring Cannon Beach, you have less than a two-hour drive to get back to Portland. This drive is very easy and quite scenic.

I love how you can see the progression as you leave the beachy coast of Oregon and head up through the mountains before coming through a tunnel and arriving back in Portland.

If you didn’t have enough time to explore Portland at the beginning of your Oregon road trip itinerary, now is a great time to have a day or two in the city.

If you are flying out the same day you leave Cannon Beach, the drive from Cannon Beach to Portland is very easy with little traffic so as long as you leave enough time.

Now you know how to plan a trip to Oregon and see all the best towns, slices of coastline, waterfalls, and hidden gems!

I hope you have a great time exploring Oregon by car! Next, check out my tips for traveling to Oregon !

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Reader Interactions

May 4, 2019 at 4:15 pm

this is so helpful! would you be able to share places to stay or where you stayed along the way?

May 5, 2019 at 1:53 pm

We stayed in a variety of Aribnbs and also hotels. If you have a place you are looking at [a city for example] we can try and remember where we stayed! We should update this post with all that information! Sorry we haven’t!

May 6, 2019 at 1:36 pm

planning a july trip. DO you know if we could route this to include Crater lake but keep around the same time frame if we were to skip Eugene, Willamette and Cottage Grove?

May 6, 2019 at 10:04 pm

Yes that is totally doable!!! And keeping it around the same time!

October 8, 2020 at 2:27 pm

Hi. I want to thank you for your great road trip guide. We did this trip in summer 2019 in an Rv in 3 weeks. A beautiful state, very friendly people. Our kids loved it. We liked Omsi science museum in Portland for kids. Kings wine estate was an experience for us and kids to. Did spent lots of time in Powel book store. Thanks again. Warm greetings from Aruba, Joost

October 8, 2020 at 2:39 pm

Enjoy!!!!! It is so much fun! Thanks for commenting!

May 23, 2021 at 2:25 pm

We would like to do this in 10 or 11 days, but thinking of eliminating Eugene for Crater lake as well. We really love Hiking and the animals, photography. With that being said should we eliminate Eugene and replace with crater? Also want to dig for a day for Sunstone so what area would require 2 nts to do so?? . Thanks, Lisa

May 24, 2019 at 12:36 pm

Cannon beach is gorgeous. Stop at Tillamook for some ice cream. Drift Creek Falls is a nice hike to a suspension bridge. Heceta Head Lighthouse, Hobbit trail to the beach. Sisters, Oregon is a cute little town. Trillion Lake. We did so much more in a week. I planned it all thru Pinterest but due to wildfires, Gorge was closed. Can be reached for more info and pics

May 24, 2019 at 1:42 pm

YES! Pinterest is such a great resource!

May 24, 2019 at 8:44 pm

This is an awesome itinerary. Planning to go July mid. Is it a good time to do Oregon? Can I know how many days trip is this? from the day you guys land to when you flew back? What places did you guys spend the nights? We will plan the similar way.

May 24, 2019 at 11:18 pm

You can do it as long or short as you want. We flew in and out of Portland and took two weeks to do it. Another time we flew into Eugene and did the bottom half of this itinerary and just looped back around in 2 weeks too but we like to spend a long time at each destination. You can do it shorter if you don’t want to spend multiple days seeing each thing!

May 24, 2019 at 10:43 pm

Nancy Can you share your itinerary? We are going for a week and wanted to cover everything in Oregon.

May 27, 2019 at 6:12 pm

Planning a week in June/July, want to see as much as possible, probably skip the eastern Oregon things, can you share itinerary you did? Where should we make sure and see?

May 28, 2019 at 12:42 pm

Great reviews and tips! So many of these places are on my list!

I’m heading to Oregon/CA for 2 weeks this summer with my husband and son and am planning the following… Columbia River Gorge 2 nights, Mt Hood 1 night, Bend 2 nights, Crater Lake 2 nights, Redwoods/Klamath 4 nights, Yachats 2 nights. Then we have a final day to head back to Portland for the flight out… so, question for all… would it be better to continue up the coast from Yachats toward Seaside and spend the last night in the state on the beach or head inland and spend our final day touring wineries in the valley?

June 18, 2019 at 1:45 am

I live in Oregon. I vote go inland.

June 22, 2019 at 4:51 pm

Definitely go inland and explore the Willamette Valley! It’s beautiful during the summer and McMinnville has beautiful wineries and tasting rooms. Go to Durant Farms, the view is stunning!!!

September 20, 2020 at 2:48 am

This is crap. You claim it to be an “Oregon” road TRIP but it is nothing more than a northwest Oregon trip. There is no central Oregon, and there is definitely not anything closely related to eastern Oregon. Stop claiming something

June 8, 2019 at 10:25 pm

This was the perfect itinerary for my trip to oregon – barely did any planning other than reading up on here and a little more for each place! We did a 6 day trip, cutting out a few things but loved every minute of this trip! Thanks for sharing!!

June 8, 2019 at 10:33 pm

That is SO AWESOME to hear! And exactly why we designed it this way! Cut out what you want or don’t have time for and do the rest!

June 21, 2019 at 5:50 pm

You COMPLETELY missed Eastern Oregon!!! And, in my opinion, you missed some of the best gems of the state! i.e. The Steens Mountains! Owyhee Canyon Country! Joseph, Oregon and the Imnaha’s. To bad! More for the rest of us! 🙂

June 22, 2019 at 12:35 pm

We can only write on what we have seen and been to or else it wouldn’t be fair 🙂

December 19, 2019 at 5:23 pm

Agree 100%! There are so many things to see in Eastern Oregon: Jon Day Fossil Beds National Monument (Painted Hills are part of), Pendleton Underground Tours, stunning views along Hwy 395, Wallowa Lake and Mt. Howard, Hells Canyon, Baker City and Sumpter, Rome Pinnacles, Owyhee River Gorge, Steens Mountain (breathtaking!), Alvord Desert, Crack-in-the-ground, Hole-in-the-ground, Newberry Crater National Monument (obsidian flow, lava tube cave, lava cast forest) and so many more! And a side note: we here in Eastern Oregon really don’t consider Bend to be a part of EO; Bend is Central Oregon! 🙂

June 22, 2019 at 3:15 pm

Love this! I will return and print out maps. Thanks so much

June 22, 2019 at 4:49 pm

You should also come and visit McMinnville, Oregon if you’re into wine tastings they have some beautiful vineyards and amazing views if you know where to look! (I don’t live there I just think it’s beautiful.)

October 23, 2019 at 3:39 pm

Hello This is awesome. Just reading about motivated for me to do this road trip. We are planning to do this during the thanks giving time. I know it is not the best time but just want to do it as much as we can. We waited so long to go to Oregon so now we thought we will start off. Do you have any suggestions or recomendations. Thank you

June 23, 2019 at 1:02 pm

We are heading to Eugene in July and will have 5 days do day trips. Eugene will be our hub each night. What do you suggest as must see locations? Thanks. We have seen Florence and Cottage Crove on a prievous trip. I love wine!

June 24, 2019 at 9:47 pm

Oh gosh so many! Def Proxy Falls, Terwilliger Hot springs, Koosah and Salahie. If you can, make it up to Salem and silver falls state park. You can also go to Smith Rock its far but amazing!

July 4, 2019 at 2:28 am

Man, if you ever edit or add to this Ashland has to be on that list. Best small town in Oregon, the food, the hikes, the Shakespeare festival!

July 30, 2019 at 8:26 am

Planning a week in December, want to see the beautiful scenes, probably skip the west part of Oregon . What should be the best place to stay there ?

July 30, 2019 at 2:11 pm

Hello! We recommend hotels for each and every stop on this list! Please let us know if there is a specific area you don’t see! If it isn’t on this list it is probably something we aren’t super familiar with! Thanks1

September 10, 2019 at 2:44 pm

Great information! Planning an anniversary trip in September and want to see the Coast, Columbia River Gorge, and Willamette Valley and whatever else we can fit in to our schedule. Arriving early to Portland on a Thursday morning. Do you suggest we head to the coast right away and head south to avoid crowds there and work our way back to Portland from Bandon to fly home on Tuesday evening? Not sure how to plan our itinerary to dodge weekend traveler crowds. Of course, I am sure we will need to plan another trip to see more of this beautiful state.

October 18, 2019 at 4:00 pm

Can anyone help? We are visiting Portland for only 3 full days. Any ideas for a condensed road trip? We are flying in on a Thursday afternoon. We have Fri-Sun for full travel days and then need to be in Portland to fly out very early in the AM on Monday. This is taking place next week so October. We have already been to Astoria, Cannon Beach and the surrounding areas a few years ago. So we don’t need to hit up those areas. Oregon is so beautiful that we want to go back. And I’m the type of person that usually wants something new and don’t visit a place twice. Love this state!

October 18, 2019 at 4:07 pm

I recommend the Columbia River Groge and Mount Hood. OR Head down to Salem and the amazing waterfalls in that area like Silver Falls State Park! Have fun!

October 22, 2019 at 7:56 pm

It’s November a good month to do this trip?

October 24, 2019 at 2:07 pm

Yes! It will be cooler out but should be a lovely time and very moody and misty!

January 20, 2020 at 1:56 am

Um hello? You forgot Crater Lake! One of the most important bucket list locations in Oregon! I would suggest driving to Grants Pass and the Oregon Caves from Bend via the Crater Lake route/Medford. Much better than cutting through Eugene. From a lifelong Oregonian.

January 20, 2020 at 2:15 pm

Thanks for sharing!! I’ve actually NEVER BEEN to Crater Lake despite all of our trips so I would feel weird suggesting a place in Oregon we had not been!!!

May 23, 2021 at 2:26 pm

May 23, 2021 at 11:04 pm

Totally suggest the eugene area for hiking! So many epic waterfalls nearby! I would eliminate crater lake and go for Eugene region for hiking! lots of good stuff!

May 24, 2021 at 5:33 pm

Thanks! Do you know if we can add the day or half day of digging for sunstone on this itinerary? The one mine is located near Plush Oregon. Lisa

May 24, 2021 at 11:46 pm

I am not familiar with this activity but Plush is VERY far away from anything on this itinerary. It is in the southeast corner of the state. I would suggest skipping it and choosing something else fun!

July 8, 2022 at 11:58 am

Does it make sense to start in Portland, drive to Eugene while doing all the things listed in between Portland and Eugene and then driving back up to Cannon Beach and flying out of Portland all in 6 days? Would that be a good trip or should I add/subtract some?

July 16, 2022 at 5:11 pm

I think it is fine to do all of these things! I would cut off samuel H boardman in 6 days as it is too far south, but the rest is very doable and I have done that exact same trip before!!!! Thank you!

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The Epic Oregon Road Trip Itinerary

This Oregon Road Trip Itinerary will help you live an epic and fabulous adventure through this glorious Pacific Northwest state. Mountains, waterfalls, river gorges, dense forests, a fairy-tale coast, wineries, hot springs, wonderful cities, ghost towns, and the USA’s deepest lake. Oregon impresses with its attractiveness and variety of landscapes. We show you must-see stops and things to do. Oregon is also a picture-perfect state, so we tell you the best photo spots to catch its wild natural beauty. We give you also hints on where to stay and what to pack. So, check our Epic Oregon Road Trip Itinerary with lots of tips and photos to prepare for an adventure.

Oregon Road Trip Itinerary – Introduction

We fell in love with Oregon on our first visit and have been to it several times. We admire this state because of its incredible beauty and variety. Moreover, we love to photograph waterfalls, mountains, covered bridges, and original architecture in Oregon.

My partner Chris and I developed this itinerary based on our experiences and insights. We show you the places you should not miss during the Oregon Road Trip. All photos presented in this article we took during our several Oregon road trips.

How many days do I need for the Oregon Road Trip?

Oregon is beautiful, so the longer the road trip you plan, the better. Our itinerary includes a 10-day Oregon road trip that begins and ends in Portland . A 10-day Oregon road trip will allow you to enjoy this state, see its greatest attractions, and take great photos.

But at the end of this article, you will find tips on what to add to your itinerary if you have 14 days . We also tell you how to shorten this plan if you only have 7 days to travel and want to see as many places in Oregon as possible.

Below, you will find our plan at a glance. Later, each day is described in detail with the itineraries, road suggestions, driving time, the most interesting stops, and attractions. We assure you that you fall in love with this state after seeing these places and want to return to Oregon.

The Epic Oregon Road Trip Itinerary Overview

Day 1. Arriving at Portland and exploring Portland. Day 2 . Driving to Mount Hood and hiking in the Mount Hood area. Day 3. Sightseeing of Shaniko Ghost Town and driving to Sisters. Day 4. Exploring Sisters and Bend – Willamette National Forest area. Day 5. Driving to Crater Lake National Park and Umpqua National Forest. Day 6. Exploring Crater Lake National Park. Day 7. Driving to Oregon Coast and Oregon Coast Road Trip. Day 8. Oregon Coast Rod Trip – exploring Oregon Coast. Day 9. Exploring Oregon Coast and return to Portland. Day 10. Exploring Portland and Columbia River Gorge/Multnomah Falls.

What Should You Know About Oregon Before You Go On A Road Trip?

• Oregon is a state where you  refuel your car without leaving it . At the gas station, you are served by a gas station employee . Refueling by yourself in Oregon carries a fine of up to $500. It’s similar only in New Jersey. It is worth remembering this when planning your Oregon road trip. This rule does not only apply to motorcyclists.
• There is  no sales tax in Oregon . Therefore, it is a state worth visiting, if only for shopping. Oregon is one of only five states (alongside New Hampshire, Montana, Delaware, and Alaska) where the price you see on the product is what you pay at the checkout. So, it’s worth shopping in Oregon. The best shopping in Portland.

What is the best time for Oregon Road Trip?

Oregon is attractive all year round. It all depends on your favorite outdoor activities and the way you travel. But this Oregon road trip itinerary is fully usable during the summer and fall months from May to the end of October.

Some of the recommended places to visit are inaccessible in winter due to closed roads. However, we tell you which roads are closed in winter so that you can also adapt your itinerary to the winter months.

Summer and Fall are also the best months for all our suggested activities. Pleasant weather enables longer hikes in the fresh air. The days are also long, so you will see more places and drive longer distances.

However, most tourists will certainly be in the high season in July and August. Therefore, if you are going during these months, we suggest that you start your sightseeing in the morning to avoid the crowds.

Oregon Road Trip Map

Please, take a paper map for your Oregon road trip. You will need it. Believe us, very often, there is no phone coverage, and you must use the traditional map. We love modern apps, but they have become useless in places like mountains, deep forests, and challenging hikes. So, a paper map is best when no cell service exists.

We use Benchmark Oregon Road & Recreation Atlas . It is very informative and detailed. Thanks to this atlas, our trips were more interesting, as we could quickly learn what was nearby and plan our route. It’s also a useful alternative to GPS maps when traveling.

Where to stay during the Oregon Road Trip?

It all depends on your needs, travel style, and budget. We traveled both by car and slept in lodges/hotels and by an RV, and stayed at campsites. Therefore,  we recommend specific lodging options for each day of the trip—only those we checked and were satisfied with—hotels and RV campgrounds for each location .

But no matter what you decide,  book your accommodation well in advance .

If you plan camping in Oregon, check our Car Camping Checklist.

What to pack for the Oregon Road Trip?

Our journey leads through the mountains, dense forests, waterfalls, hot springs, and heavenly beaches, so you should pack properly. Oregon’s climate is temperate but fairly humid, with frequent rainfall. The humidity is felt in the mountains and forests, so always be ready for rain.

Please check our detailed  Day Hiking Packing List  to see what to pack for hiking trails.

Furthermore, check our  Road Trip Packing List Essentials  to make your Oregon Road Trip safe and comfortable.

Day 1 Oregon Road Trip Itinerary: Arriving in Portland and exploring Portland

Arriving in portland.

Our Oregon road trip begins in the capital of the state – Portland. The city has an international airport, so it’s the most convenient way to get there. You can rent a car from the rental located at the airport.

Lodging in Portland

For this Oregon road trip itinerary, we recommend you book 2 nights in Portland – the first and the last . Of course, you can modify the plan to your needs.

During our few trips, we stayed in the  Courtyard by Marriott Portland City Center . We really enjoyed staying here. Our room was clean, and it had a lot of space, the service was great.

We also stayed in the  Mark Spencer Hotel , which is fabulous, in the city’s heart. But check below on the Deals finder the best offers.

During the last trip with the motorhome, we stopped at Portland Fairview RV Park .

Sightseeing Portland

Portland is a delightful city, so we’ve put together a detailed Portland Itinerary . What do we suggest you see during the day after your arrival? Start from Downtown Portland and the river waterfront loop. It’s a 2.6-mile loop that runs right along the Willamette.

There are 12 fabulous bridges over the Willamette River. If you have time, visit Portland Japanese Garden and go to the Pittock Mansion situated 1,000 feet above the city.

Day 2 Oregon Road Trip Itinerary: Driving to Mount Hood and hiking in the Mount Hood area

Drive to timberline lodge & mount hood.

Take US-26 W and drive to the Mount Hood area. The drive will take you about 2 hours, and it is a scenic route.

Lodging in the Mt Hood area

We suggest 1 night in the Mount Hood area in this Oregon Road Trip Itinerary.

Timberline Lodge is a historic beauty hotel near the magnificent Mount Hood. Moreover, the psychological horror “The Shining” from 1980, directed by Stanley Kubrick, was shot at the Timberline Lodge. You can check our photos from this fabulous and thrilling filming location here. If you can, stay overnight at Timberline Lodge. If the place is busy, choose one of the nearby accommodations. Nearby are Best Western Mt. Hood Inn , The Mt. Hood Oregon Resort .

Hiking in the Mount Hood area

No matter where you stay for the night, head to Timberline Lodge and see this fabulous scenery. Moreover, they have great restaurants where you can have lunch or dinner. Finally, the Timberline Lodge parking lot provides access to many trails on the flanks of Mount Hood. So, you can choose one or two hikes in Mount Hood National Forest.

• Mountaineer Trail Loop Hike is a great hike because there is such an easy road that goes so high on the mountain. The distance is 2.7 miles. The easiest hiking opportunity is to stroll in any direction you feel like.
• Zigzag Overlook Hike is also easy to hike. The distance is 4.4 miles. You will see the alpine areas of Mount Hood’s south side. You’ll pass alpine and subalpine meadows to reach an overlook over the deeply gouged Zigzag River Canyon, with the craggy ramparts of Mount Hood above.
• Paradise Park from Timberline Lodge Hike is a longer but fabulous hike. The distance is 12.1 miles, and it isn’t easy. Is a classic mountain trek. In addition to the mountain vistas and wildflowers, the route passes several waterfalls and offers unique views of the high country south and west of Mount Hood.

Day 3 Oregon Road Trip Itinerary: Sightseeing of Shaniko Ghost Town and driving to Sisters

Drive to shaniko ghost town and explore it.

From Mt Hood, take OR-216 and in Maupin, take Bakeoven Road. It’s about 77 miles and 1 hour 45 minutes driving to Shaniko. You need about 2-3 hours to explore Shaniko. From 1903 Shaniko gained the nickname “Wool Capital of the World.” 

You will find an old railway station, antique items, and wooden architecture from over 100 years ago. The town has an amazing history. You can read more about it and check more our photos in our post- Shaniko Ghost Town .

Drive to Sisters

From Shaniko, take US-97 S and OR-126 W to Sisters. It’s 84 miles and about 1 hour and 40 minutes driving.

Sisters is a fabulous town, surrounded by mountains and forests. We detailed described its attractions in post Things to do in Sisters .

We also described interesting routes in the area there. Situated in the foothills of Oregon’s Cascade Range, Sisters and Bend are perfect for holidays. Moreover, it’s a great idea to spend here also winter vacation if you like skiing.

Lodging in Sisters or Bend

We suggest 2 nights at Sisters during your Oregon Road Trip. The area is fabulous. However, it might be difficult to stay overnight in the summer. Therefore it is also worth considering the nearby Bend. It’s about 25 minutes from Sisters. It is a larger city and has a well-developed accommodation and catering base. It’s worth visiting Bend for sure.

Best Western   Sisters Oregon is our favorite one. It is a small, charming Ponderosa Lodge with 48 oversized guest rooms renovated in a country theme. Tasty breakfasts and friendly service. 

If you need RV camping, the best RV park in the area is  Bend / Sisters Garden RV Resort . But you have to  book it well in advance . It’s closest to the Sisters, located in a beautiful setting, and it’s hard to get a spot, especially in high season.

Hotel rates in Bend are much more affordable than in Sisters, so consider this place for optimizing your holiday budget.

Day 4 Oregon Road Trip Itinerary: Exploring Sisters and Bend – Willamette National Forest area

We suggest you actively explore the Willamette National Forest area on this day. Below are three of our favorite hikes. They are not long, so it is possible to make them in one day. Or you can choose the ones that suit you best. Prepare some more snacks and lunch.

Sunrise or early morning hike at Sparks Lake

Sparks Lake is 49 miles and an hour’s drive from Sisters. You have to drive through Bend. So, take US-20 E to Bend and turn onto Cascade Lakes National Scenic Byway. The scenery is breathtaking. If you like sunrises – they look fabulous in this place. But you can also go there during the day for a walk. This road may be closed in winter.

Proxy Falls Hike & McKenzie Pass Scenic Byway

Proxy Falls, AKA Lower Proxy Falls, is a dazzling cascade waterfall hidden in the Three Sisters Wilderness. It’s near McKenzie Pass and McKenzie River in the Willamette National Forest. From Sisters, it is only 28 miles and approximately 50 minutes drive via OR-242 W. For more photos and tips, see our Proxy Falls Hike post . The best idea is to combine this hike with The McKenzie Pass-Santiam Pass Scenic Byway. Oregon Route 242, known as a portion of the McKenzie Highway, takes you on a journey through a land of contrasts. You’ll encounter lush forests, crystal-clear lakes, and lava fields on the west side of the Cascades. Stop at the  Dee Wright Observatory . In our opinion, Route 242 is one of the most scenics, so it’s a must in Oregon Road Trip Itinerary. This road is closed in winter.

Tamolitch Blue Pool Hike

Tamolitch Falls, also known as Blue Pool due to its amazing blue color of the water, is a popular hiking spot in  Willamette National Forest , Oregon. The deep turquoise and stunning clarity of the Blue Pool make this place unforgettable. The approximate hike time is 1 hour and 30 minutes one way. From Sisters stay on US-20 West. Then turn onto OR-126 E for 10.8 miles. Turn right at a sign for Trailbridge Campground/Blue Pool. You must cross a bridge and turn right onto gravel road NF-730. After about a third of a mile, park along the right side of the road.

Day 5 Oregon Road Trip Itinerary: Driving to Crater Lake National Park via Umpqua Hot Springs

Saok in umpqua hot springs.

From Sisters is 115 miles and 2 hours 15 minutes driving via US-97 N to Crater Lake National Park . But we suggest you take a bit off course and soak into one of Oregon’s best hot springs – Umpqua Hot Springs.

So if you like hot springs, take from Sisters US-97 S and OR-138 W to get to Umpqua Hot Springs. It’s 2 hours 45 min driving (143 miles). They are located in Umpqua National Forest. This set of 7 geothermal pools sits right on the edge of a rock face, spilling 108-degree water into the North Umpqua River below. The view is breathtaking. There is a short hike to get to the hot springs. It should take you 20 minutes to get to the pools. For more photos, hike & trailhead descriptions, hot springs etiquette, you can check in our Ultimate Guide to Umpqua Hot Springs in Oregon .

Driving to Crater Lake National Park and Lodging option in the area

The Oregon road trip itinerary would not be complete without a visit to a fairy-tale volcanic Crater Lake. You are less than an hour’s drive to Crater Lake National Park from the hot springs, depending on where you are staying. Try to reach the sunset because they are spectacular above Crater Lake. It is the only national park in Oregon. Moreover, it is the deepest lake in the USA with the clearest and bluest water in America. We prepared a detailed guide to this place with tips, so read Top Things To Do in Crater Lake National Park .

If you plan your Oregon road trip in May or the beginning of June, check the weather on the NPS website . Sometimes in May, there is still a lot of snow. You can visit the park, but some roads might be closed.

Lodging option

We suggest 2 nights at the Crater Lake NP area. Crater Lake Lodge   is a historical lodge inside the Park. Unfortunately, it’s not easy to book it. It’s pretty expensive. Moreover, it’s open only from May – September, filling up guests quickly.

But Chiloquin is only 8.5 miles from Crater Lake National Park, so check accommodation there. 

If you are looking for a campground Diamond Lake Resort & RV Park  is a great place to relax. It’s only 4 miles to Crater Lake park entrance, so the location is perfect. Book in advance.

But if you plan a winter trip, 1 night in Crater Lake should be enough because some roads and trails are closed. So, 1 day for sightseeing in winter will be optimal.

Sunset at Crater Lake and Crater Lake Rim Scenic Drive

Crater Lake looks great before and just after sunset. The light is the warmest then. The water surface is flickering. The historic  Crater Lake Rim Drive is a 33-mile (53-km) long road , which offers breathtaking and panoramic vistas of the lake, forests, and meadows. Along the way, there are 30 overlooks with ample car parking, which provide opportunities to stop for views, admire it, relax, taking photos.

Day 6 Oregon Road Trip Itinerary: Exploring Crater Lake National Park

On this day of the Oregon Road Trip Itinerary, we focus on exploring Crater Lake National Park’s beauty. If you can do it, get up for the sunrise. The view is worth your effort. Have a picnic at one of the viewpoints. Take one or two trails. We describe 7 Best Day Hikes in Crater Lake National Park  from easy to strenuous here . It’s worth visiting Rim Village Visitor Center and Crater Lake Lodge.

Day 7 Oregon Road Trip Itinerary: Driving to Oregon Coast and Exploring Oregon Coast

From this day, we start the Oregon coast road trip itinerary. The coast of Oregon is very varied. Rocky, sandy, covered with dense forests, often shrouded in fog. Look carefully and you will see seals or sea lions basking on the rocks. Moreover, you can encounter coyotes, roe deer, and deer on the slopes of rocks and in coastal forests. As well as gulls, hawks and other birds.

Drive to Oregon Coast

Start driving early in the morning. You have almost a 4 1/2 hours drive to the Oregon coast.

Stop at the Girardet Vineyards

If you have more time and are a wine lover, you can change the route a bit and make a short stop on the way to the coast. You can stop at Tenmile in Girardet Winery and Wine Cellar . The place is unique. You will not only taste and buy excellent wines here, but you will also meet wonderful people who create this winery with a passion.

Moreover, if you have more time for your Oregon Road Trip, consider staying in their fabulous Chardonnay Chalet at the Vineyard . The address of Girardet Winery is 895 Reston Road, Roseburg, OR 97471. From Crater Lake, drive via OR-62 W to get there. It’s 119 miles and 2 hours 30 minutes driving. They are open Wednesday-Sunday from 11 a.m. – 5 p.m., year-round. Moreover, they are RV friendly and Family & Pet Friendly.

Stop at the Cape Blanco Lighthouse

Cape Blanco Lighthouse is the first fabulous stop at the coast in this Oregon Road Trip itinerary. To get there directly from the Crater Lake NP, take OR-42 E and OR-138 E. It’s 205 miles and 4 hours 20 minutes driving. If you are going from Girardet Winery, take OR-42 W and US-101 S. It’s 90 miles and 2 hours of driving.

Drive to Cape Arago Lighthouse and lodging

The next stop is at Cape Arago Lighthouse. It’s 53 miles and a 1 hour 15 minutes drive from Cape Blanco. Take the US – 101 N. Cape Arago is stunning to get there. Therefore, we suggest accommodation in this area. So, Book 1 night here.

If you are traveling by RV, book an advance spot in Sunset Bay State Park .

Exploring Cape Arago

We like this place because, in a small area, you have as many as three great state parks offering stunning views of the Oregon Coast.

• Cape Arago State Park
• Shore Acres State Park
• Sunset Bay State Park

So, start this afternoon and evening by visiting each of these parks and taking at least a short walk along the coast. Wait for the sunset.

Day 8 Oregon Road Trip Itinerary: Oregon Coast Rod Trip – exploring Oregon Coast

It’s another intense day exploring the Oregon coast and a lot of driving. Therefore, start your day early. Pack some snacks for the road.

Drive and stop at Umpqua River Lighthouse

The next interesting stop we suggest doing in our Oregon road trip itinerary is Umpqua River Lighthouse. It’s 45 minutes (32 miles) from Cape Arago via Cape Arago Hwy and US-101 N.

Stop at Heceta Head Lighthouse Scenic Viewpoints

From Umpqua River, take US-101 N and drive about 40 miles (55 minutes) to the next scenic viewpoint: Heceta Head Lighthouse.

Stop at Rockaway Beach

Next stop during this Oregon Coast road trip plan at Rockaway Beach. It’s 122 miles and about 2 hours and 45 minutes driving via Oregon Coast Hwy.

Sunset at Cannon Beach and lodging

Rockaway Beach is just a 40-minute drive and 26 miles from Oregon’s famous Cannon Beach. Try to get there at sunset.

We suggest booking 1 night in this beautiful area. If you are looking for something special, you can choose one of the exclusive beachfront hotels as Surfsand Resort or Hallmark Resort .

If you’re traveling in a motorhome, a great place to spend the night is Cannon Beach RV Resort . Book it in advance. A great choice is also Seaside RV Resort .

Day 9 Oregon Road Trip Itinerary: Exploring Oregon Coast and returning to Portland

This is the penultimate day of our Oregon Road Trip Itinerary. We suggest you focus on the rest of the Oregon coast. You can stay in Cannon Beach and relax on the beach. Except for Cannon Beach is worth visiting Ecola State Park and taking Clatsop Loop Trail to see Tillamook Rock Lighthouse.

Or you can continue to go north. You can drive to Lewis and Clark National Historical Park and Astoria (it’s about 40 minutes from Cannon Beach). If you decide to go through Astoria, visit Astoria Pier and Marina, Cathedral Tree Trail, and Astoria-Megler Bridge.

Moreover, you can check Goonies’ film locations. And then, from Astoria, drive via US-30 E and I-5 S and return to Portland. It’s 105 miles and 2 hours of driving.

If you have more time, you can go shopping in Portland. Remember that there is no sales tax in the state of Oregon, so it’s worth shopping here. It is much cheaper. For more things to do, you can check in our detailed 3 days in Portland Itinerary .

Day 10 Oregon Road Trip Itinerary: Exploring Portland and Columbia River Gorge/Multnomah Falls

We don’t know how much time you have on the last day of your Oregon road trip, so modify it according to your needs. If you do not have too much time on day 10, transfer your visit to Multnomah Falls and Columbia River George to day 9 or 1 of the Oregon Road Trip Itinerary.

Multnomah Falls is an icon of the Pacific Northwest. So, it’s worth your visit. It’s only 40 minute drive from Portland. More photos, tips, and directions we described in a separate article about Multnomah Falls and Columbia River Gorge .

How to shorten this Oregon Road Trip Itinerary to 7 days?

If you only have 7 days for your Oregon road trip and you would like to see all the places we write about, we suggest the following solution. Book 1 instead of 2 nights in Sisters / Bend. Remove Tamolitch Blue Pool Hike from the plan. Book 1 instead of 2 nights at Crater Lake NP. Make only a scenic drive loop and stop at the park’s best viewpoints. Finally, shorten your stay on the Oregon coast.

How to extend this Oregon Road Trip Itinerary to 14 days?

If you have 14 days for your Oregon Road Trip, you can, of course, spend more time in each place we describe. Depending on your preferences, you can spend more time in the mountains or at the seaside.

Add to your Oregon Road Trip Itinerary Alvord Desert and Hot Springs

But you can also visit other interesting places . One of our favorites we suggest adding to your Oregon road trip itinerary is Alvord Desert with Alvord Desert Hot Springs and Crystal Crane Hot Springs .

If you want to see the desert and desert hot springs, adding them to your Oregon road trip itinerary is best after visiting Sisters and Bend. So, take US-20 E and OR-78 E to get there. It’s about 260 miles and 4,5 hours of driving.

Add to your Oregon Road Trip Itinerary Covered Bridges of Oregon

Another option is adding some covered bridges to your Oregon road trip itinerary. We have described the most beautiful Oregon-covered bridges . It’s best to add them to your Oregon Road Trip Itinerary on your way to Crater Lake NP. Detailed GPS coordinates you will in our post.

We hope this article helped you plan your Oregon Road Trip. If you like our Oregon Road Trip Itinerary, please share it! We wish you a fabulous Oregon adventure!

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Agnes Stabinska is a writer, photographer, and co-founder of The Van Escape. She loves wildlife, landscape photography, and outdoor adventures, especially hiking, camping, and exploring U.S. national parks. Although she has traveled to many countries for almost 20 years, her favorite places are Alaska, the American Southwest, and the Pacific Northwest, which she often visits and explore with her partner, Chris. Their travel tips, itineraries, and recommendations will help you get away from it all and plan a wonderful vacation.

15 Comments

The only place I have done in the Pacific North West is Cape Flattery and Seattle and as an outdoor person, I got a lot to do in Washington, Montana and also Oregon. I have always dreamt of going to Oregon and try and hit up as much as I can including the Pacific Crest trail. You have giving me more ideas on your list here including those waterfalls! I might wait until my daughters have got a bit older so we can do outdoorsy stuff together. (living in the UK sucks sometimes when all the amazing nature stuff in the US is on the west coast!) 😛 

Well I guess I would have been $500 without reading this article. I’m not used to states where they fill up your gas tank for you! Ten days still doesn’t seem like long enough to see all of these sites. My gosh, the state is so beautiful especially Multnomah Falls, Crater Lake and the Hot Springs. I just want to see it all! Maybe I should move, lol.

You sure take some really good photographs. The waterfall  has given me new goals. And I would love to see Shaniko. In India, we don’t fill our own fuel, so that part is easy to handle. But the drive looks super in Oregon. 

So glad I came across this Oregon road trip itinerary! I am planning a road trip from Minnesota to the west coast for this upcoming summer and didn’t know where I should go…. Now I know, Oregon! I have been to Seattle and many spots in California, but haven’t been to any of these beautiful spots in Oregon.

I would like to visit Oregon, especially the coast and the hot springs. As of now, I prefer to stay away from Portland area. I think I read about Sister from your post before. Interesting town. So, by cross out Portland from the itinerary, 7 days will be enough for us.  

I have been wanting to visit Oregon for a while so this is a great comprehensive list of things you must see. I love all the nature and scenic views, so I’m sure a road trip is a great way to embrace that! Thank you for all the information!

I haven’t been able to do too many road trips till now except few when in Europe. This Oregon road trip certainly looks one I must do. Thanks for all the comprehensive information which would certainly help when we plan a trip there. Seeing the bridges of Oregon would be exciting too.

PNW has long been in my bucketlist! I can imagine doing it on a roadtrip with a campervan. The trails, nature and mountains that can be witnessed seem so amazing. I love your waterfall additions. This road trip will def be on our dream destinations one day.

Wow that’s interesting that in Oregon there are people to fill the fuel and doing on our own attracts a fine. Coming from India this is common but in Australia we have to do it on our own. Anyway I have never been to Oregon and this road trip definitely seems epic and the pictures look awesome. I will keep this itinerary in mind when I plan a trip in future.

Wow, what a great comprehensive guide to visiting Oregon! I’ve always wanted to visit Crater Lake and now I have even more places to add to my list. There really is something special about the Pacific Northwest, it’s such a gorgeous area.

Ooh saving this. What a fab looking itinerary. I have travelled extensively around the US but not been around Portland and Oregon yet. Keep hearing good things. May have to wait a while before returning to the States, but this trip will be high on my list!

What a great Oregon road trip itinerary! Yes, I would add more time at the vineyards, but that’s just me! I would also love to just sit out and watch the seal & sea lions! I think I would also really enjoy visiting the Crane Hot Springs Resort! 

Truly Oregon is such a pretty state. We’ve done all those you mentioned here. Perhaps more days for Bend, Painted Hills, and caves of Oregon!

Love the ghost town you mentioned and the wineries you included! so cool!

This was one very detailed itinerary for a road trip in Oregon. I don’t think I’ve seen anything that comes close to offering this level of information for a holiday idea. The photos you used are amazing as well. If I live in the US, I would definitely try this road trip out

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The Perfect Oregon Road Trip Itinerary: Must See Stops and Things to Do

Oregon is a picture-perfect coastal state in the Pacific Northwest known for its astounding views, outdoor lifestyle, and wild natural beauty. It is home to one of the largest river gorges and to the deepest lake in the United States. Discover the best it has to offer with this ultimate two week Oregon road trip itinerary.

Oregon Road Trip Summary

How many days does it take to road trip Oregon? You can spend months exploring the country’s ninth-largest state, but if you don’t have that kind of time, you can cut it down anywhere from a 5 day Oregon road trip to two weeks. 

Ideally, you should plan at least a week to two weeks to truly appreciate its beauty.

Plan your road trip along this loop starting and ending in Portland, it will take you to many of the highlights.

• Astoria, 1 night
• Cannon Beach, 1 night
• Newport,1 night
• Florence, 1 night 
• Brookings, 1 night 
• Crater Lake National Park, 3 nights
• Bend, 2 nights
• The Dalles, 2 nights
• Portland, 2 nights

Oregon Road Trip Map

Best Time of Year 

The best time of year to plan an Oregon road trip depends on the activities you are interested in and your budget. 

Summer is the most popular season, from wine tasting to biking in pleasant temps. But, it comes with occupied rooms and a hefty price tag. No road-tripping on the fly during peak season.

Fall is met with sunny skies, crisp air, and an array of orange, yellow, and red leaves. Even though you can expect a few sprinkles, it’s a popular time for hiking, pumpkin patches, and festivals. 

The rainy and winter season between October and May triggers lower hotel costs and fewer tourists with moderate temperatures. Winter activities include skiing, tubing, sledding, hot springs, and snowmobiling. Just make sure to pack layers!

Then spring arrives with new growth and invigorating temps; it’s a good time to see wildlife and the many waterfalls throughout the state. 

When it comes to outdoor adventure, Oregon has something to offer in any month.

HOT TIP: If you want to spot migrating gray whales on the coast, plan your visit from March through May or mid-December through mid-January.

Car Rental Tip – How to Avoid High Prices

Car rentals in Oregon – on the entire West Coast actually – are significantly higher than those in other areas of the country. When we first started researching prices, the search engines came up with $80 – $85 per day!

A tip we learned is to book offsite away from the airport and take public transportation or a Lyft to the rental company. 

Ultimately, we ended up with a Budget Rent a Car fifteen minutes from the airport and paid $29 per day with taxes and fees during peak season.

RELATED: CROSS COUNTRY ROAD TRIP

*Disclaimer: This post contains affiliate links, if you book through our link we will receive a small commission at no additional cost to you. Thanks for supporting the blog!*

Day 1: Astoria

Once you pick up your rental car, kick off this ultimate Oregon road trip in Astoria, the oldest settlement west of the Rockies. Sitting on the banks of the Columbia River and only a few miles away from the Pacific Ocean, the small city is more like a historic fishing village with a Victorian flair.

If you’ve ever seen the 80’s coming-of-age film, The Goonies , then Astoria might look a little familiar to you. Hop on a pilgrimage around town and try to find all the locations. 

What to See & Do: Goonies Film Locations, Astoria Pier and Marina, Astoria Column, Cathedral Tree Trail, and Astoria-Megler Bridge.

Where to Eat & Drink: Coffee Girl, Buoy Beer Company, Bowpicker Fish & Chips, or Fort George Brewery.

Where to Stay: Waterfront Hotel with Indoor Pool & Free Breakfast, walking distance to all attractions

Day 2: Cannon Beach

It’s time to hop on Highway 101, the 347-mile scenic road to discover Oregon’s beautiful and wild coastline. Cannon Beach is a short drive from Astoria so you can technically pick one or the other destination if you need to shorten your trip, but I think it deserves an overnight.

Once listed as “one of the world’s 100 most beautiful places” by National Geographic, Cannon Beach has a lot to see and do including exploring the quaint town itself.

On the Way: Fort Stevens State Park, Wreck of the Peter Iredale, Lewis and Clark National Historic Park, walk the Seaside promenade, and eat at Bell Buoy of Seaside.

What to See & Do: Ecola State Park, Cannon Beach, Clatsop Loop Trail to see Tillamook Rock Lighthouse (bring binoculars), and Haystack Rock. 

Where to Eat & Drink:  Public Coast Brewing Company, Lazy Susan Cafe, Castaways, or Pelican Brewing Company.

Where to Stay: Beachfront Lodge with Continental Breakfast or Inn with Breakfast & Garden

HOT TIP: You can see all kinds of diverse marine life on Oregon’s beaches, it’s one of the top things to do when exploring the coast. The best time to go tidepooling is one to two hours before the low tide. Check the tide times here.

READ NEXT: AN EASTERN OREGON ROAD TRIP

Day 3: Newport

There are a lot of stops along the two-and-a-half-hour drive to Newport, one of the biggest cities on the coast. From the aquarium to the glassblowing studio, there’s a lot to choose from once you get there. 

If you want to do something unique, reserve a pedal-powered quadricycle at Oregon Coast Railriders in Wheeler and go for an 11-mile jaunt through the countryside on an unused railroad track.

On the Way: Haystack Rock, Oswald West State Park, Neahkahnie Mountain Trail Viewpoint, Silver Point Interpretive Overlook, Tillamook Creamery, Cape Meares Lighthouse, Octopus Tree, Cape Lookout, Beverly Beach State Park, Cape Foulweather, Devils Punchbowl State Natural Area, and Yaquina Head Lighthouse.

What to See & Do: The Oregon Coast Aquarium, Historic Bayfront, Oregon Coast Glassworks, Hatfield Marine Science Center (it’s free with a suggested donation so you can stop in for as long as you’d like), sunset on Nye Beach, and the Farmer’s Market on Saturdays.

Where to Eat & Drink: Georgie’s Beachside Grill, Carl’s Coffee, Local Ocean Seafoods, Chowder Bowl, Rogue Ales and Spirits, or Panini Bakery.

Where to Stay: Adorable and Highly-Rated Motel with balconies and fireplaces

Day 4: Florence

Discover one of the most photographed lighthouses in the United States, go underground in a large sea cave to find grunting sea lions, and explore a quiet gem on the coast. 

Around mile marker 164 you’ll find Yachats, pronounced Yah-hots, a welcoming small village at the mouth of the Yachats River. If you have time stop in Yachats Brewing for quality beer and farm-to-table cuisine. 

You’ll spend the night situated on the banks of the Siuslaw River in the charming riverfront district of Florence. 

On the Way: South Beach State Park, Seal Rock State Recreation Site, hike the one-mile loop at Yachats Ocean Road State Park, Devil’s Churn Scenic Overlook, Cape Perpetua Lookout,  Thor’s Well, and Neptune State Scenic Viewpoint.

What to See & Do: Eat on the river, Take a Dune Buggy Tour, Florence Old Town, Hobbit Trail with the China Creek Trail, Heceta Head Lighthouse, and Sea Lion Caves. 

Where to Eat & Drink: River Roasters, Homegrown, BJ’s Ice Cream Parlor, or Waterfront Depot Restaurant.

Where to Stay: Charming Motel with a Cabin-Vibe walking distance to Old Town

RELATED: NORTHEAST ROAD TRIP ITINERARY

Day 5: Brookings

After leaving Florence, you’ll travel from sandy dunes to the untamed wild section of the drive. With mountains and forest on one side and the tumultuous ocean on the other, the scenery is spectacularly dramatic. 

More than likely, the road will be uncrowded with a quiet fishing port or artsy town popping up here and there. Four of the eleven lighthouses on Oregon’s waterfront line the southern stretch and it feels like every few miles you’re running into a state park. 

Stop just six miles short of the California state line for your overnight in Brookings, the southernmost city on the coast. 

On the Way: Simpson Reef Overlook, Face Rock State Viewpoint, Sunset Bay State Park, Shore Acres State Park, Cape Arago Lighthouse, Coquille River Lighthouse, Face Rock State Scenic Viewpoint, Sisters Rock State Park, Pelican Bay Lighthouse, and Cape Blanco Lighthouse.

What to See & Do: Samuel H. Boardman State Park, Azalea Park if visiting in the spring, Port of Brookings-Harbor Marina Boardwalk, Harris Beach State Park, and Chetco Point Park

Where to Eat & Drink: The Crazy Norwegians Fish and Chips, Tasty Kate’s, Khun Thai.

Where to Stay: Comfy Beachfront Hotel with Water Views

*If you wake up early enough the next morning, drive the extra 23 miles south to Redwood National and State Park for a detour if you’re like us and love to see all the national parks.”

Days 6 – 8: Crater Lake National Park

Crater Lake is one of the most magical landscapes in the United States. Many people asked if our pictures were filtered and if the lake really is that blue. And I’m here to tell you yes, it really is that blue. 

Formed in the remains of an ancient volcano, at 1,943 feet deep, it is the deepest lake in the United States and one of the top ten on earth. Excellent visibility, measured at 144 feet, along with the depth and purity contributes to the brilliant blue color.

Any southern Oregon road trip should include this stop! Plan for at least three days so you can hike, take the scenic drive, and a boat tour of the lake. 

What to See & Do: Rim Village Visitor Center, Crater Lake Rim Scenic Drive, Watchman Trail, Standard Boat Lake Cruise which includes the Cleetwood Cove Trail, Garfield Peak Trail, Crater Lake Lodge, and the Discovery Point Trail. Read about our favorite hikes here at The Best Crater Lake Hiking Trails.

Where to Eat & Drink: Pack in your own lunches, Prospect Cafe, Crater Lake Lodge, and Prospect Pizza.

Where to Sta y:   Hotel & Suites near the Park or Mountain Cabin with Balcony

NEARBY: OLYMPIC NATIONAL PARK

Days 9 – 10: Bend

If looking up real estate the first day of a visit is any indication of how impressive an area is then Bend is uber awesome. You’ll only be able to scratch the surface of all this mountain town has to offer within a few days so you’ll definitely be planning another trip back.

Situated in the foothills of Oregon’s Cascade Range, the upscale community is at the core of an outdoor playground with countless activities throughout the entire year. The attractive downtown area has a wide range of hip coffee shops, local eateries, and innovative art galleries.

On the Way: Take the Cascade Lakes National Scenic Byway and pull over at a few of the lakes with lunch or drinks at Elk Lake Restaurant. 

What to See & Do: Try a local craft brewery, Todd Lake Loop Trail, Walk around Downtown, Tumalo Falls, Old Mill District, and Smith Rock State Park.

Where to Eat & Drink: The Cafe, Crux Fermentation Project, Spork, Bangers & Brews, and Wild Rose Northern Thai Eats.

Where to Stay: Welcoming Hotel with Free Breakfast, Beautiful Views in a Great Location near the Old Mill District.

Days 11 – 12: Columbia River Gorge 

Let’s adventure into America’s largest National Scenic Area, the Columbia River Gorge. Separating Washington and Oregon, this vast meandering canyon delivers breathtaking views, gorgeous waterfalls, and endless outdoor activities.

From the historic Crown Point Vista House to the horseshoe-shaped Rowena Crest viewpoint, it is a drive that you will never forget.

On the Way: Detour to Mount Hood, Oregon’s highest mountain, and hop on the Scenic Sky Chairs for a bird’s-eye view of the surrounding mountain ranges. 

What to See & Do: Elowah Falls, Bridge of the Gods, Multnomah Falls, Latourell Falls, Crown Point, Bonneville Lock and Dam, Bridal Veil Falls, Rowena Crest, Horsetail Falls, Wahkeena Falls, Hood River, and the Vista House.

Where to Eat & Drink: Thunder Island Brewing Co, The Gorge White House, Full Sail Brewing Company, Tad’s Chicken N’ Dumplins, and Columbia Gorge Hotel.

Where to Stay: Hidden Gem of a hotel with Fantastic River Views

HOT TIP: Include the 35-mile Hood River County Fruit Loop to your itinerary for a scenic drive with charming orchards, bountiful vineyards, fruit stands, and even an alpaca ranch. 

Days 13 – 14 Portland

The City of Roses pounds to an eclectic beat, and with its prime location in the Pacific Northwest there are a ton of things to do outdoors including gardens and parks. Read here for other Outdoorsy Day Trips from Portland. 

Bearded hipsters, emerging artists, and skilled brewmasters converge amid two mountain ranges to form Portland. With that in mind, there’s no shortage of breweries, galleries, coffee shops, donuts, or food trucks within the metropolis.

What to See & Do: Portland Japanese Garden, Washington Park, Best Rooftop Bars in Portland , International Rose Test Garden, Pioneer Courthouse Square, Powell’s City of Books, and Pittock Mansion. 

Where to Eat & Drink: Rogue Ales, Hawthorne Asylum Food Cart Pod, Radio Room, Culmination Brewing, Homegrown, Voodoo Doughnut Old Town, and Prost!

Where to Stay: Boutique Hotel with Bike Rental and Wine Reception

HOT TIP: If you don’t want to spend the money for the Japanese Garden, you can link from the MAC trail to a series of switchbacks on the Wildwood Trail for a glimpse overhead. 

Have you taken an Oregon road trip? What do you recommend?

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Angela E. is a travel writer from the Chicagoland area who has visited all 50 states in the US and has traveled extensively around the world. She is passionate about exploring the great outdoors and hiking in particular. Her love for nature has taken her to some of the most beautiful locations on the planet. She has written extensively about her travels on her own website, Dang Travelers, and has been published in collaboration with other travel websites and multiple visitor bureaus around the country.

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5 Responses

Dan coleman.

I enjoyed reading about your trip all over Oregon. By any chance do you remember the exact Budget Rental car location address you picked up your car?

Dang Travelers

Hey Dan! It was the Budget at 5856 NE Columbia Blvd, Portland, OR 97218

Were the hikes you mentioned fairly easy? What about ticks, Is that something to prepare for? And last, do you think this could be done in a week? I know we wouldn’t be able to spend several nights in each place and wouldn’t be able to do or see everything but the highlights.

A week is pretty short for the entire loop, but you might be able to swing it. There are some great hikes in Crater Lake, but you could also just spend a day there (take the boat ride and see the views from the overlooks) and drive the coast.

And we had no issues with ticks at all.

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Best Oregon Road Trip Itinerary for 7 to 10 days (2024)

I recently made a road trip across Oregon with my family and was mesmerized by Oregon’s untamed beauty!

Nestled in the Pacific Northwest region of the United States, Oregon offers a mesmerizing blend of rugged coastline, dense forests, cascading waterfalls, and bustling cities.

On our road trip, we covered the Oregon Coast from Canon Beach to Newport, explored the cities of Portland and Bend, awed at Crater Lake National Park, and marveled at the natural beauty of Columbia River Gorge, Smith Rock State Park, and Hood River.

Whether you are starting your Oregon road trip from California or Portland, I have detailed itineraries outlined in this post for both routes.

Let’s plan the perfect Oregon itinerary and get ready for an unforgettable journey through the heart of the Pacific Northwest!

In a hurry and looking for the best recommendations for your Oregon road trip?

➡ Below are my top recommendations for places to stay along the Oregon road trip:

• Portland – Hyatt Centric Downtown Portland
• Cannon Beach – Surfsand Resort
• Newport – The Inn at Nye Beach
• Ashland – McCall House Boutique Inn
• Crater Lake – Crater Lake Lodge
• Bend – The Oxford Hotel
• Hood River – Columbia Gorge Hotel and Spa

➡ Top Excursions from Portland:

• Best of Portland Morning City tour
• Multnomah Falls and Columbia River Gorge Waterfalls Tour from Portland
• Oregon Coast Tour from Portland

➡ If flying into Portland, you will need a rental car . I recommend Discover Cars for the best rates!

Planning the perfect Oregon Road Trip Itinerary

You can do the Oregon Road trip two ways –

• Flying into Portland city and making a loop road trip that starts and ends in Portland
• If you are in Northern California (like me), start and end your Oregon road trip in California. I started from San Francisco Bay Area and did a loop Oregon road trip.

Oregon road trip itinerary from California

I live in the San Francisco Bay Area, and we did the Oregon road trip loop driving from California.

Below is our Oregon road trip itinerary from San Francisco Bay Area covering Bend, Hood River, Columbia Gorge and Multnomah Falls, Portland, Cannon Beach, Tillamook, Newport, and Ashland.

We went from Bend to Hood River and then to Portland. From Portland, we went west to the Oregon Coast and explored Cannon Beach, Tillamook, and Newport. Finally, we went inland to Ashland before driving back to California, thus completing our loop.

California to Oregon road trip itinerary for 7 to 10 days

• Day 1: Drive from San Francisco Bay Area to Bend, stay overnight in Bend
• Day 2: Explore Bend, stay overnight in Bend
• Optional day add-on: Day trip to Crater Lake National Park
• Day 3: Bend to Portland Scenic Drive, Hood River, Columbia Gorge, overnight in Portland
• Optional day add-on: Stay overnight in Hood River
• Day 4: Explore Portland, stay overnight in Portland
• Optional day add-on: Stay overnight in Cannon Beach
• Day 5: Explore Oregon Coast, stay overnight in Newport
• Day 6: Explore Newport, overnight in Ashland
• Day 7: Drive back to San Francisco Bay Area

We only had seven days for this route trip, so it was very jam-packed and involved a lot of driving. Driving from San Francisco Bay Area to the Oregon border itself takes around 5 hours one way.

If you have more time, I suggest adding a few more days to your road trip to allow additional days in Bend, Hood River, Portland, and the Oregon Coast.

Map of Oregon Road Trip Route from California

Click here to see the map of this route in Google Maps.

Oregon road trip itinerary from Portland

If you are flying in from another state into Portland, then your Oregon road trip itinerary will start and end in Portland.

You can drive first to the west of Portland towards the Oregon Coast or drive east towards Hood River and Bend, depending on accommodations availability.

Oregon road trip itinerary from Portland for 7 to 10 days

• Day 1: Arrive In Portland. Stay overnight in Portland.
• Day 2: Explore Portland. Stay overnight in Portland.
• Day 3: Drive from Portland to Oregon Coast – Cannon Beach, Tillamook. Stay overnight in Newport.
• Optional day add-on: Stay overnight in Cannon Beach and explore Astoria as well.
• Day 4: Explore Newport. Drive to Ashland. Stay overnight in Ashland.
• Day 5: Drive to Bend. Stay overnight in Bend.
• Day 6: Explore Bend. Stay overnight in Bend.
• Day 7: Bend to Portland Scenic Drive, Hood River, Columbia Gorge. Return to Portland

Map of Oregon Road Trip Route from Portland

Extending Oregon Road Trip from 10 days to 2 weeks

10 to 14 days is the ideal duration for an Oregon road trip so that you have more days to explore and relax. With seven days, it will be a lot of driving each day and less time at each place.

We made this Oregon road trip from California in a week due to time constraints, and it was a lot of driving most days and less time for exploration. We were still able to see all the highlights and saved the hidden gems for future trips.

With only seven days, you will not be able to see everything and will have to pick only the must-do sights.

Also, there won’t be time to do some of the longer hikes, and you will have to stick to the short hikes or walks to the Vista points. Luckily, we found that all the popular attractions in Oregon are just a short walk from the parking lot.

Below are some suggestions to extend your road trip to Oregon beyond seven days:

• Visit Crater Lake National Park as a day trip from Bend or stay overnight in Crater Lake.
• Stay overnight in Hood River.
• Stay an extra day in Portland to explore the various neighborhoods.
• Explore Astoria and stay overnight in Cannon Beach (add a day here).
• Extend the Oregon Coast route further down Newport to Florence (add a day) or all the way to Brookings (add two days).

Places to explore on Oregon Road Trip

No matter which road trip itinerary route you choose, whether starting in Portland or California, below are the must-do stops and destinations on your Oregon road trip.

For each of these places, I have listed the top things to do there and accommodation suggestions for where to stay overnight.

If you are flying into Oregon for this road trip, then you most probably will start and end your road trip in Portland, which is the largest city in Oregon.

Plan to spend at least one full day, i.e., two nights in Portland or more. We reached Portland in the evening and stayed for two nights. This gave us a full day to see the sights in downtown Portland.

Top things to do in Portland

We had one day of sightseeing in downtown Portland, and below are some of the must-do sights in your Portland itinerary based on my research and experience.

You will need a car to see some of these places as they are a bit uphill, like the Pittock Mansion and Washington Park, but others are walkable if you stay downtown.

With just one day in Portland, I highly recommend taking a city tour if you want to make sure you can cover all the sights. Of course, you can also see the sights on your own by driving around.

➡ Check rates and availability for this Best of Portland Morning City tour or Best of Portland Afternoon City tour covers the top sights. Perfect if you have limited time in Portland!

Pittock Mansion

We drove straight to Pittock Mansion in the morning to see the famous city views. It’s only around 12 minutes from downtown by car. There is a small parking lot here with a fee.

This historic house museum sits atop a hill, providing stunning city views. You can explore its elegant rooms and learn about the city’s heritage through exhibits and artifacts.

The mansion has an entry fee, but it is free to explore the grounds and admire the views of downtown Portland.

Washington Park

Washington Park in Portland is a sprawling urban park offering diverse attractions like the International Rose Test Garden , Portland Japanese Garden , Hoyt Arboretum , Oregon Zoo, and Oregon Children’s Museum .

Situated to the west of downtown Portland, the park spans over 400 acres, providing a serene escape from the city’s hustle and bustle.

You would need a full day to explore Washington Park. With just a few hours, it is best to pick one of its attractions based on your interest.

We visited the International Rose Test Garden, as Portland is called the ‘City of Roses’. The rose garden is a very popular attraction here.

The rose garden had thousands of rose varieties blooming in vibrant colors during July. It was a huge and well-maintained rose garden!

Next time, we will definitely visit the Hyott Arboretum and explore the hiking trails in the urban forest. If you have time, definitely check it out.

Portland hip neighborhoods for dining

After exploring Washington Park, head to one of the cool neighborhoods in downtown Portland for a nice meal.

Northwest 23rd Ave Street is bustling with restaurants, cafes, and breweries. I loved strolling through the street and window shopping. We were in the mood for Thai cuisine and tried Thai Bloom restaurant. The food was great!

Pearl District in Portland is a trendy, urban neighborhood known for its artsy vibe, upscale boutiques, and diverse restaurants and cafes.

Powell’s City of Books

Powell’s City of Books in downtown Portland is one of the largest bookstores in the world and a must-visit while in Portland.

Powell’s occupies an entire city block and features multiple floors filled with an extensive collection of new, used, and rare books. The bookstore is so huge that they have a map of the various sections!

My entire family spent several hours here, and we left with a lot of books! Make sure to check out the Rare Books room on the third floor. It is really cool, and some of the books are really old and expensive here.

Waterfront Park

Enjoy a leisurely walk along the Willamette River waterfront and soak in the scenic views of the city and the nearby bridges.

Starting at the south end of Burnside Bridge, the Waterfront Park Trail goes on for miles and is ideal for strolling, cycling, or jogging along the Willamette River.

Note: There is quite a bit of a homeless population in downtown Portland, and you might come across them, especially near the waterfront area. During the daytime, we felt quite safe exploring downtown Portland.

Where to stay in Portland

We stayed at Hyatt Centric Downtown Portland and cannot recommend it enough! It was at the perfect location to explore all the top sights in Portland downtown. The hotel is new and very modern and has a restaurant onsite. It also has valet parking privileges for a daily rate.

But what we really loved about this hotel is the excellent and friendly staff here. Everyone we met was really awesome, with great customer service. We got a bed and breakfast rate and loved the made-to-order breakfast at the restaurant.

Oregon Coast

Being from California, we have driven along the scenic Pacific Coast Highway 1 many times, but I was equally excited to experience the Oregon Coast.

Before this trip, I had seen amazing pictures of Cannon Beach and Oregon’s famous lighthouses. Let me tell you that the Oregon Coast did not disappoint! It was beautiful and very scenic.

We tried to stop at most of the vista points along the way for some epic views of beaches and the Pacific Ocean.

We drove from Portland to Cannon Beach and then south along Hwy 101 to Newport on the same day for our road trip. We stayed overnight in Newport.

If you have an extra day, consider including Astoria, which is to the north of Canon Beach, and staying overnight in Canon Beach.

We did this particular Oregon Coast road trip in summer, but winter in Oregon Coast is equally beautiful, with coastal storms causing dramatic huge crashing waves, and a more secluded experience with fewer crowds.

Cannon Beach

Our first stop on the Oregon Coast was Cannon Beach. Cannon Beach on the Oregon coast is a beautiful coastal town known for its iconic Haystack Rock , a massive sea stack rising from the ocean.

The beach is expansive, with soft sands perfect for strolling, beachcombing, and enjoying breathtaking sunsets. There were plenty of people on the beach, even on a Wednesday morning in July.

It was a little windy on the beach, but being from Northern California, we are used to cold beaches. It’s best to dress in layers on your Oregon Coast road trip!

The Wayfarer Restaurant & Lounge is right at the beach for some seafood lunch.

Surfsand Resort is a family-friendly resort located right on the beach, offering comfortable rooms and excellent amenities.

Tillamook Cheese Factory

After Canon Beach, our next major stop on the Oregon Coast road trip was at the Tillamook Cheese factory. My teens were excited to see the factory and try the cheese samples and the famous ice cream.

Let me tell you that this was the most crowded place on the entire Oregon Coast as it is one of the most popular Oregon Coastal attractions . We had to park in the overflow lot on a Wednesday afternoon in July.

The factory offers self-guided tours to see the cheese-making process and sample various kinds of cheese. There are paid tours as well, but as we didn’t want to be timebound, we just did the self-guided tour.

The self-guided tour was great, and there were free samples of cheese and cheese curds. The cafe has some great lunch and snack options, and the deep-dish pizza was great.

Make sure to try the Tillamook ice cream! Tillamook is famous for its creamy, indulgent ice cream, available in a range of delectable flavors.

Treat yourself to a scoop or two in a waffle cone or cup – the perfect way to cool down on a summer day. They have some great flavors, including new ones that are not found in stores.

Three Capes Scenic Drive

Between Tillamook and Newport is the very scenic stretch of the Oregon Coast called the Three Capes scenic drive or loop. As we were headed to Newport, we did not do this as a loop but just as a one-way drive.

The Three Capes are Cape Meares, Cape Lookout, and Cape Kiwanda . After Tillamook, Hwy 101 goes inland, and you will have to take a detour on Hwy 131 and up Netarts and Oceanside to reach Cape Meares.

Cape Meares was my favorite as it has a cool lighthouse, a short walk over a paved trail from the parking lot. The trail has a slight downhill incline on the way to the lighthouse.

Another attraction at Cape Meares is the Octopus tree . There is a short dirt trail in a beautiful forest to reach it. It’s just 0.2 miles and an easy walk. The unique Sitka Spruce tree is estimated to be around 300 years old and 16 feet wide!

Cape Lookout State Park has a beautiful wide beach, campground, and hiking trails for some epic views. We just stopped at the Cape Lookout viewpoint for some panoramic views of Cape Lookout Beach and Netarts Bay.

Cape Kiwanda is at the northern end of Pacific City Beach. This cape is famous for its massive sand dune, known as the “Giant Sand Dune.”

You can climb the sand dune for panoramic views of the coastline and the surrounding landscape. We stopped at Pacific City Beach to admire the Cape Kiwanda sand dune.

After Pacific City, you merge back to Hwy 101 and continue South. There are several nice beach towns along the route, like Lincoln City and Depoe Bay if you would like to stop for food.

Newport, Oregon

Finally, after a long day of driving along the Oregon Coast and admiring some amazing coastal views, we reached Newport.

Newport, Oregon, is a coastal town known for its picturesque beaches, historic Bayfront, marine life, and Yaquina Head Lighthouse.

It is one of the larger towns on the Oregon Coast and a great place to stay for the night or a couple of nights.

Top things to do in Newport

Yaquina Head Lighthouse is the most stunning lighthouse on the Oregon Coast. From the viewpoint behind the lighthouse, we saw several whales spouting far off in the ocean!

There is an entry fee of around $7 to enter the Yaquina Head Outstanding Natural Area. There are several hiking trails here and beaches like Quarry Cove and Pebble Beach. The entire area is really serene and beautiful, with 360-degree ocean views.

Nye Beach is the most popular beach in Newport for strolling along the beach, watching the sunset, or dining at restaurants along the beach.

Newport Historic Bayfront is a bustling shopping and dining hub with seafood restaurants like Clearwater. Admire the views of the Yaquina Bay Bridge from the waterfront.

Oregon Coast Aquarium is a fun place to see marine animals like sharks, sea otters, and colorful fish.

Where to stay in Newport

Elizabeth Oceanfront Suites is a great place to stay in Newport with Oceanfront rooms. As we had only one night’s stay on the Oregon coast, I wanted an oceanfront room to get the full Oregon coast experience.

We got a large room with two king beds. It had a balcony with beach and ocean views and a fireplace! It was amazing to watch the sunset right from our balcony! I could see the lighthouse in the distance as well.

The Inn at Nye Beach is another great place to stay right on Nye Beach, with oceanfront rooms and a Spa. It also has breakfast and parking included.

Bend, Oregon

Bend is a great stopover in your Oregon road trip itinerary for a couple of nights. It is renowned for its abundant recreational activities and vibrant community. Bend has an amazing downtown in the Old Bend area and a newer Old Mill District.

We stayed two nights in Bend and really enjoyed strolling through the town, exploring the cafes, shops, and restaurants. We also did a half-day trip to visit the Smith Rock State Park for hiking.

There are some great day trips you can do from Bend, like Crater Lake National Park, Smith Rock State Park, and Hood River.

Top things to do in Bend

Floating the Deschutes River: During summer months, floating down the Deschutes River on inner tubes or inflatable kayaks is a popular pastime for locals and a must-do in Bend in the summer! It’s a relaxing way to enjoy the scenery and soak up the sun.

Old Mill District : A lively area with a charming riverfront, the Old Mill District offers shopping, dining, and entertainment. Enjoy a leisurely stroll, catch a movie at the cinema, or dine in one of the excellent restaurants. Our hotel was right next to Old Mill, and we enjoyed eating at Pastini and watching the people floating down the Deschutes River.

Pilot Butte State Scenic Viewpoint – In the evening I highly recommend hiking or driving to the top of Pilot Butte, a small volcanic mountain in Bend for some 360-degree panoramic views of Bend town and the surrounding mountain ranges!

Tumalo Falls : Take a short drive of around 30 minutes west of Bend to see the impressive Tumalo Falls. The viewing area is a short walk from the parking lot and offers a stunning vista of the cascading water. You can hike to the upper viewpoint of Tumalo Falls for a closer look.

Smith Rock State Park : Located just outside Bend, Smith Rock offers breathtaking rock formations and is a popular destination for rock climbing, hiking, and photography. The Misery Ridge Trail provides stunning views of the Crooked River Canyon.

Drake Park and Mirror Pond : Stroll through Drake Park, a beautiful park in the heart of Bend, and enjoy the tranquil scenery surrounding Mirror Pond. It’s an ideal spot for a picnic or a relaxing afternoon.

Bend Ale Trail : For beer enthusiasts, Bend boasts an impressive number of craft breweries. You can explore the Bend Ale Trail, sampling some of the finest brews in the Pacific Northwest.

Newberry National Volcanic Monument : This volcanic area in Deschutes National Forest is great for exploring unique geological features, such as lava tubes and obsidian flows. Take the park shuttle or hike to the top of Lava Butte for some excellent views of the caldera and the surrounding area.

Where to stay in Bend

Bend has quite a few areas where you can choose to stay. You can stay near the Old Mill District, near the Old Bend downtown, or a little further away from the main town.

The Oxford Hotel Bend is a great luxury boutique hotel right in the Bend downtown area and within walking distance to restaurants, shops, and Drake Park. Unfortunately, it was sold out for our travel dates.

Hampton Inn & Suites Bend is a mid-range hotel right next to the Old Mill District and Hayden Homes Amphitheater. This is where we stayed, and we loved the proximity to Old Mill dining and being able to walk on the trail along the Deschutes River. Great rooms, free breakfast, and parking. It also has an indoor pool.

Tetherow Resort is an upscale hotel with a golf course near the Deschutes National Forest. Great location for recreational activities like hiking in summer and skiing in winter. Has a pool and several restaurants onsite.

Bend to Portland (or Portland to Bend) Scenic Drive

Portland to Bend or Bend to Portland scenic drive is one of the best drives in an Oregon road trip. I liked this road trip stretch even more than the Oregon Coast drive.

To travel from Bend to Portland or vice versa, the scenic drive is the US-97N and US-26W route via Hood River and Columbia Gorge which is often called the scenic route.

Below are the stops we made along the Bend to Portland scenic drive:

• Smith Rock State Park – excellent for hiking and rock climbing
• Scenic Drive through Mount Hood National Forest along US-26 W
• Hood River and Hood River fruit loop

Multnomah Falls

• Historic Columbia River Highway and vista points

If you are driving from Portland to Bend instead, do these stops in the reverse order starting with the Historic Columbia River Highway.

Smith Rock State Park

Our first stop in the Bend to Portland scenic drive was Smith Rock State Park. This iconic destination offers incredible rock formations and is a favorite spot for rock climbers and hikers. The views of the Crooked River Canyon are awe-inspiring.

Misery Ridge Trail is a challenging hike leading to the top of Misery Ridge, offering panoramic views of the Crooked River and Monkey Face rock formation.

For an easier short hike, try the River Trail, which is an easy trail along the Crooked River, perfect for a leisurely walk with beautiful views of the cliffs. We hiked this trail, but note that there is some elevation to get down to the river trail from the parking lot.

Hood River is a great place to stop for a few hours or overnight on your Oregon road trip between Portland and Bend. Hood River is around 1 hour from Portland and around 3 hours from Bend.

Hood River is a mecca for windsurfing and kiteboarding enthusiasts. This charming town also offers excellent dining options, boutique shops, and stunning river views.

We just spent a few hours here, but Hood River is also a great weekend getaway destination. Next time we plan to stay here overnight for sure!

Top things to do in Hood River

At Hood River, you will find plenty of small businesses to explore, ranging from breweries, wineries, and produce farms. The riverfront town also offers plenty of water recreational activities.

Hood River Fruit Loop

Exploring the Hood River fruit loop is one of the top things to do in Hood River.

This self-guided tour takes you through picturesque orchards and farm stands, offering a taste of the region’s freshest produce, artisan foods, and delightful U-pick experiences during the harvest season.

We stopped at Hood River Lavender Farms, and it was so beautiful. I enjoyed picking a bouquet of lavender to bring home with me. Their store has a lot of high-quality lavender products like essential oils, bath and body products, and edible lavender to purchase.

Hood River Waterfront Park

This beautiful park along the Columbia River provides a perfect setting for picnics, kite flying, and relaxing by the water. The park offers stunning views of the Gorge and opportunities for waterside walks.

Windsurfing and Kiteboarding on the Columbia River

Hood River is a popular destination for windsurfing and kiteboarding enthusiasts. The consistent winds and stunning views of the Columbia River Gorge make it a paradise for water sports enthusiasts of all skill levels. It was fun to watch the kiteboarders from the waterfront park.

Visit Local Wineries and Taste the Region’s Wines

Hood River is part of the Columbia Gorge AVA, known for its excellent wines. Take a scenic wine tour and visit some of the charming wineries to taste a variety of wines, including award-winning Pinot Noir and refreshing white wines.

Relax at Hood River’s Craft Breweries and Enjoy Local Beers

Hood River has a thriving craft beer scene, with several breweries offering a variety of handcrafted beers. Relax on brewery patios, sample seasonal brews, and enjoy the laid-back atmosphere of this small town.

Downtown Hood River

Hood River’s downtown is a charming area with unique boutiques, art galleries, and craft stores. Here you can browse for local handmade items, artwork, and souvenirs and dine at the various restaurants.

Where to stay in Hood River

Hood River has a good mix of unique boutique hotels to familiar chain hotel brands, so you will definitely find something to match your needs.

Columbia Gorge Hotel and Spa is an excellent riverfront hotel with a spa, golf, and restaurant onsite. Get a room with views of the Columbia River! This hotel is in a quite location but minutes away from the Hood River town area.

Westcliff Lodge is a great place to stay, with views of the Columbia River and just minutes from the Hood River city center. The hotel has nice grounds and is pet-friendly.

Hampton Inn & Suites Hood River is at a great location within walking distance of Hood River Waterfront Park and the restaurants in Hood River city center. The hotel has free breakfast, free parking, and an indoor pool and hot tub.

Historic Columbia River Highway Scenic Drive

The Historic Columbia River Highway is a scenic drive that winds through the Columbia River Gorge in Oregon, offering breathtaking views of majestic waterfalls, lush forests, and dramatic cliffs.

The historic Columbia Gorge Highway is only a 40-minute drive from Portland and Hood River. The historic scenic highway runs parallel to _84 and has several amazing waterfalls and vista points along the way.

Multnomah Falls is probably the most famous waterfall in Oregon! I had seen pictures of this cascading waterfall earlier, and it was on my bucket list!

Multnomah Falls is a two-tiered cascade totaling 635 feet in height. There is a main viewing platform for the lower-tier falls. A paved trail takes you to the Benson Bridge, providing a perfect vantage point to marvel at the falls.

The falls were spectacular, but the entire area was very crowded on a Monday afternoon in July. There was no space to stand on the bridge!

To park at the larger parking lot on I-84, you will need to make a parking reservation on the official Recreation.gov website. A permit is only required during the busy summer months from May to September.

There is a smaller parking lot on the historic Columbia River Highway that does not require a permit.

Note that you cannot drive directly between the two parking lots as they are on different roads which do not connect at Multnomah Falls. You will have to go a bit further up or down the historic highway to get on I-84.

Bridal Veil Falls

This graceful waterfall tumbles around 120 feet, resembling a bridal veil. From the Bridal Veil Falls State Scenic Viewpoint, you take a short hike through a lush forest that leads to a viewing platform, offering a picturesque perspective of the falls.

Latourell Falls

Latourell Falls cascades 249 feet over a striking basalt cliff. A short 1-mile hike from the highway takes you to a viewpoint where you can admire this magnificent waterfall up close.

Vista House at Crown Point

Vista House, perched on Crown Point, is a historic observatory, and the grounds provide sweeping views of the Gorge and the Columbia River below.

It’s a fantastic spot for photos and to admire the Columbia River and Gorge separating the Washington and Oregon states.

Portland Women’s Forum State Scenic Viewpoint

The Portland Women’s Forum State Scenic Viewpoint is an overlook that provides stunning panoramic views of the Columbia River Gorge, including the iconic Vista House at Crown Point and the majestic river below.

The viewpoint is named in honor of the Portland Women’s Forum, a group of influential women who played a significant role in advocating for preserving the Columbia River Gorge as a scenic area.

Crater Lake National Park

Crater Lake is the only National Park in Oregon and a must-visit in any road trip itinerary for Oregon.

I had made a separate trip to Crater Lake National Park before, so I skipped it on this trip, but if you have not been to Crater Lake, I highly recommend you make a day trip from Bend or stay overnight in Crater Lake National Park.

Top things to do in Crater Lake

Hiking : Explore the network of Crater Lake hiking trails , ranging from easy walks to challenging hikes, offering spectacular vistas of the lake and surrounding forests. I highly recommend the Cleetwood Cove Trail, which takes you to the lakeshore.

Boat Tours : During the summer months, take a guided boat tour on Crater Lake to experience the lake up close and learn about its geology and history. It was my favorite thing to do in Crater Lake. You can also visit Wizard Island on the boat tour.

Scenic Drive : Take a drive around the rim of the caldera for breathtaking views of Crater Lake from various vantage points, including Rim Village and Watchman Overlook.

Where to stay in Crater Lake

Crater Lake Lodge : Located right on the rim of the caldera, Crater Lake Lodge offers stunning lake views and a historic atmosphere. It’s the most iconic lodging option inside the National Park. This is where we stayed during our visit to Crater Lake.

Crater Lake Resort is just a 12-minute drive from the park and has multiple cabins with private bathrooms and furnished tents to choose from.

Ashland, Oregon

Ashland is the perfect small town to stop on your Oregon road trip, whether traveling between California and Portland or doing a loop road trip from Portland.

Ashland is around a 5-hour drive from both Portland and the San Francisco Bay Area, making it the best place to stop on your road trip.

When planning the road trip, I debated whether to stop in Medford or Ashland, but the charming downtown of Ashland seemed really nice. Also, there are some really nice bed and breakfasts in Ashland .

Also, I found this amazing boutique hotel in Ashland downtown – McCall House Boutique Inn . Staying in this preserved historic Inn built in 1883 was the highlight of our trip.

Top things to do in Ashland

Oregon Shakespeare Festival : Ashland is famous for the Oregon Shakespeare Festival . Watch world-class theater performances in beautiful outdoor venues. We were lucky to catch an outdoor performance happening on the evening of our visit.

Lithia Park : A beautiful picturesque park right in the middle of the town with gardens, walking trails, a creek, and a duck pond.

Ashland downtown: Ashland has a Hallmark movie-style charming downtown with restaurants, art galleries, boutiques, and shops.

Where to stay in Ashland

We stayed at the historic McCall House Boutique Inn . It was at the perfect location, and we could walk to the Oregon Shakespeare Festival, restaurants, and Lithia Park.

The house itself was beautifully renovated with all modern amenities inside. The rooms have unique decor, and the freshly prepared breakfast was delicious.

Lithia Springs Resort is another great place to stay in Ashland, off Interstate 5 and within a 5-minute drive to downtown Ashland. This resort has a pool, hot tub, and spa treatments for relaxing and rejuvenating.

Travel Tips for planning your Oregon Road Trip

Below travel tips and FAQs will help with planning your Oregon itinerary.

Where to start an Oregon road trip?

If you are flying into Oregon, Portland is the best place to start and end an Oregon road trip. Portland International Airport (PDX) serves major cities in the United States.

If you live in Northern California, you can start your road trip from your city. I started my road trip from San Francisco Bay Area. Keep in mind that it takes around 5 hours to drive from Northern California to the Oregon border, so that will add to your driving distance.

If you live in Southern California, flying into Portland for an Oregon-only road trip might save on the driving time across California, but it will add the expense of flights and a rental car.

How many days are needed for an Oregon road trip?

The suggested Oregon road trip itinerary can be completed in around 7 to 10 days, depending on the pace of your exploration and the number of stops you choose to make along the way. I recommend planning at least ten days so that you can spend more time in each place, as seven days was a bit rushed.

Do you need a rental car for an Oregon road trip?

Yes, if you are flying into Portland, you will need a rental car for this road trip, as most of the places on the road trip are best explored by car.

➡ I recommend using Discover Cars as they check top car rental brands and provide the best rate!

Which is the best season for an Oregon road trip?

The ideal time for an Oregon road trip is during the summer months (June to August) when the weather is generally pleasant, daylight hours are longer, and outdoor activities are abundant. However, spring (April to May) and fall (September to October) offer milder weather and fewer crowds, making them excellent alternatives.

What should I pack for an Oregon road trip?

Pack comfortable clothing suitable for various weather conditions, including layers, as weather can change quickly. Don’t forget essentials like sunscreen, insect repellent, sturdy footwear for hiking, and a phone/camera to capture stunning landscapes.

Can I camp along the route?

Yes, there are numerous campsites and RV parks along the road trip route where you can enjoy the beauty of Oregon’s nature up close.

Is it safe to drive in Oregon during winter?

Winter driving in Oregon can be challenging due to snow and icy conditions, especially in higher elevations. It’s essential to check weather forecasts and road conditions before embarking on a winter road trip and to have appropriate winter tires or chains.

Wrap-up: Oregon itinerary

With this Oregon road trip itinerary in hand, you’re all set for an unforgettable adventure. Embrace the scenic beauty, explore the charming towns and cities, and immerse yourself in nature’s wonders.

Whether it’s the rugged coastlines or the enchanting forests, each stop in Oregon promises something unique. So, pack your car, hit the road, and get ready to create memories that will last a lifetime.

More about Oregon

17 Best Places to Visit on the Oregon Coast

7 Best Bed and Breakfast in Ashland, Oregon

3 days in Portland itinerary for an epic weekend

11 Best Crater Lake Hikes (easy, moderate, and difficult levels)

Anu Agarwal is the founder and author of vacation travel blog Destination Checkoff. Anu, a Northern California resident, and a regular nine-to-fiver, loves to vacation with her family to destinations all over the world. She is obsessed with doing endless research for her trips. She has traveled to several destinations in the United States, Canada, Mexico, Europe, and Asia. With her blog, Anu is excited to share her destination itineraries and vacation travel guides and help you check those dream destinations off your bucket list!

How to plan an unforgettable 7 day Oregon road trip

Oregon has been on my bucket list ever since I moved to Vancouver, BC, back in 2019. Fast forward four years and I finally made it down there! On our 7 day Oregon road trip, we experienced so much – from incredible beaches and sand dunes to roaring waterfalls and the high desert. 

Oregon is such a large and diverse state which can make planning a road trip quite challenging. In this blog post, I’m sharing our exact 7 day Oregon itinerary. You’ll also find optional add-ons in case you want to extend your trip, information on entrance fees, suggestions on where to stay, and more!

Disclaimer : This blog post features some affiliate links, which means I get a small commission if you make a purchase. There’s no extra cost to you but it just helps me to keep writing these free guides and itineraries for my readers. Thank you for your support!

7 day oregon road trip: what you need to know.

There are so many wonderful things to see and do in Oregon. This 7-day Oregon itinerary is based on my own experiences but you can easily tailor this to your own travel style and add or cut any stops you see fit.

7 Day Oregon Road Trip Route Overview

Here’s a quick summary of the 7 day Oregon road trip that we did. You can do this route in either direction. We went anti-clockwise as the weather looked better at the beginning of the trip so we decided to start with the coastal section.

• Day 1: Arrive in Cannon Beach
• Day 2: Cannon Beach, Ecola State Park, and Cape Kiwanda
• Day 3: John Dellenback Sand Dunes, Willamette National Forest, and Bend
• Day 4: Bend
• Day 5: Smith Rock State Park and Mt. Hood
• Day 6: Columbia River Gorge (and Portland)
• Day 7: Travel home

Below you’ll find an itinerary map for this Oregon 7 day road trip which features pins for each day’s scenic stops, hiking trails and places to eat. You can save the map by clicking on the star next to the title and use it to help gauge daily driving distances.

Before we jump in, here are some important things to know about Oregon and this road trip route:

Oregon is a big state

Oregon is a lot bigger than people realize. It’s actually the 9th largest state in the country which means you’re not going to see the entire state in one trip. Here’s a quick overview of the different regions:

• Oregon Coast: 363 miles of beaches, rugged cliffs, sea stacks and quaint towns
• Central Oregon: Home to the high desert and well-known spots like Bend, Sisters and Smith Rock State Park
• Eastern Oregon: This is a vast area that deserves its own road trip and includes the Painted Hills, Pendleton and Hells Canyon
• Mt. Hood: Mt. Hood is the highest peak in Oregon and is a popular destination for outdoor enthusiasts
• Columbia River Gorge: This is the ‘waterfall wonderland of the Pacific Northwest’
• Willamette Valley: The valley is home to vineyards, farmlands and orchards
• Southern Oregon: This is a diverse region where you’ll find Crater Lake National Park, Oregon Caves National Monument and hidden hot springs

We wanted to try and see as much of the different landscapes as we could on our 7 day Oregon road trip. We spent some time on the coast before driving into central Oregon and up to Mt. Hood and the Columbia River Gorge.

This itinerary doesn’t include Eastern or Southern Oregon as it was just too far to go on a 7 day Oregon road trip. If you do have more time, I’ve included some suggestions on how to extend this road trip later in the blog post.

Where to start and end your 7 day Oregon road trip

This really depends on where you’re travelling from. We decided to drive from Vancouver so we went straight to Cannon Beach and started our road trip from there. However, if you’re flying in I recommend starting and ending your road trip in Portland. Although it’s in the northwest corner of the state, it’s actually well-positioned for this particular 7 day Oregon road trip. From Portland you can either drive west to Cannon Beach or go east to Columbia River Gorge and do this 7 day Oregon itinerary in reverse.

If you’re planning to do a longer road trip and explore Eastern Oregon as well, I would suggest flying into Portland and out of Bend. This way you don’t have to drive all the way back to Portland.

How to get to Oregon

If you live in British Columbia, Washington or Northern California, you could drive all the way or fly into Portland and rent a car. We looked into both options but it worked out much cheaper for us to hire the car from Vancouver and drive down (we saved $300).

For those coming from further away, I’d recommend flying into Portland and renting a car . I always use  Skyscanner  to find reasonable rates on flights and use  Auto Europe  for car rentals as they have great rates.

Do you need to rent a car for this 7-day Oregon road trip itinerary?

You will definitely need to hire a car for this road trip! If you’re flying into Portland International Airport you can pick up your hire car from the airport. Make sure you book in advance to get the best price.

Alternatively, you could rent a campervan instead for this 7 day Oregon road trip. Outdoorsy  is the world’s largest and most trusted RV rental market place and have a great selection of adventure vehicles. They take care of liability and collision insurance too so it’s an easy and simple way to book an RV for your trip. My advice is to work out the costs for both options and see what is cheaper. A campervan rental is usually more expensive than a car but you don’t have to pay for hotels which can be pricey. 

When is the best time to do this itinerary?

With its diverse landscapes, Oregon offers unique experiences all year-round. That being said, I would recommend doing this 7 day Oregon itinerary in late spring or early autumn.

Spring is a great time to visit Oregon as the wildflowers are starting to appear and the weather is warming up. It’s also peak waterfall season as the snow has just melted so they’re incredibly powerful. There are usually fewer crowds but expect weekends to still be quite busy along the Columbia River Gorge. The downside is that higher elevation hiking trails will still be closed and there can be late snowfalls which lead to road closures. When we went, we couldn’t get down to Trillium Lake because the snow had blocked the entrance.

As with most places, this is peak tourist season so expect crowds and higher prices for accommodation. However, it’s also the best time for hiking, camping, and exploring the famous Crater Lake.

Early autumn is a nice time to visit. Although the waterfalls won’t be very powerful, the fall foliage is very pretty. The weather can be a bit unpredictable but there are fewer crowds and you can get some good deals on accommodation. I would avoid doing this road trip in late autumn as there are often snowfalls which can make travel more difficult.

Winter in Oregon is a magical time and offers great opportunities for skiing, snowboarding and snowshoeing. However, I would personally avoid doing this 7 day Oregon road trip in winter. Some areas on this route may be inaccessible due to snowfall and the mountain passes may even be closed due to winter storms. If you are planning a winter road trip, I would stick to the Oregon coast, Columbia River Gorge, and Silver Falls State Park as the roads in these areas are well-maintained.

Oregon itinerary driving conditions and tips

For the most part, the roads on this 7 day Oregon itinerary are very good. There are a few big pot holes on the road through the Willamette National Forest so watch out for them as some are quite deep. The road to Terwilliger Hot Springs is paved up until the last part where it becomes more rugged.

Some parts of the route are quite remote and you will lose cell coverage. I found that I didn’t have any service in Willamette National Forest and Mt. Hood. It also kept cutting in and out in the Columbia River Gorge. Most of the route is well signed but I recommend downloading offline maps or taking a physical one with you just in case. 

Make sure you stock up on groceries before you set off on day 3 and 5 because there aren’t many stores along the way. The same applies for gas. Fill up before you start the drive through Willamette National Forest and Mt. Hood.

7 DAY OREGON ROAD TRIP ITINERARY

This is quite a jam-packed itinerary so you’ll need to get up quite early each day to account for the long drives in-between some of the stops.

OREGON ROAD TRIP DAY 1: TRAVEL TO CANNON BEACH

If you’re flying into Portland and hiring a car, it’s a relatively straight forward drive to Cannon Beach. Once you get through Portland, you’ll pick up Highway 26 west to Cannon Beach for 73 miles. At the end of this highway, you’ll merge onto Highway 101 (the Oregon Coast Highway) which will take you to Cannon Beach.

The whole drive from Portland takes around 1 hour 40 minutes. Although today is most likely a travel day, depending on what time you arrive, you may be able to catch sunset on Cannon Beach.

Where to stay in Cannon Beach

There are some lovely places to stay in Cannon Beach, from oceanfront hotels to guest houses and campgrounds. Here are my top picks:

• Tolovana Inn: We stayed here and I can’t recommend it enough! It’s right on the beach but as it’s a bit further down it’s more affordable than other oceanfront hotels. The staff were so helpful and the rooms were modern and so comfortable. In the morning, we walked out of the hotel and straight onto the beach. It was such good value for money. Check prices > 
• Surfsand Resort: This is another oceanfront hotel but it is closer to the haystack so it’s more expensive than Tolovana Inn. If you’re celebrating a special occasion then have a look at their ocean view rooms. Check prices >  
• Wright’s for Camping: This is a great option if you’re planning to drive and camp. It’s a family-run campground offering affordable camping close to the beach. The campground is only open from May to October. Check prices >      

OREGON ROAD TRIP DAY 2: CANNON BEACH TO LAKESIDE

Wake up early and get ready for a busy day of exploring beaches and sand dunes along the Oregon coast!

First Stop: Cannon Beach

If the weather is on your side, I recommend getting up early and going for a sunrise walk along Cannon Beach. It’s such a lovely way to wake up and means you’ll get to experience the beach before it gets too busy. When we went, sunrise was at 7.15am and we were two of the only people on the beach. Watching the sun light up the famous Haystack Rock was incredible.

If you love photography, walk up the steps which are opposite the Haystack Rock (leading up to the houses and beachfront hotels). This will give you a lovely view looking down at the Haystack Rock. It’s a classic view so you’ve probably seen it on Instagram but it really is worth the hype.

After you’ve finished walking along the beach, wander into the town and grab some breakfast. Cannon Beach Bakery and Lazy Susan Café are great options. The town itself is very quaint so it’s worth popping into a few of the local stores.

Second Stop: Ecola State Park

• Driving time: 11 mins (4.6 km/ 2.9 miles)

The next stop is Ecola State Park. It’s only a 10 minute drive north of Cannon Beach and is a lovely area to explore. Set in a lush rainforest, Ecola State Park is home to old-growth trees, pristine beaches and stunning coastal views.

There are a number of great hikes in the park, such as Ecola Point to Crescent Beach (1.25 miles) and Clatsop Loop (2.8 miles). Ecola Point to Indian Beach (1.5 miles) is another lovely trail. If you’re short on time (remember you do have a long drive ahead of you!) or don’t fancy hiking too far, you can drive to Ecola Point. From there, it’s a very short walk to the viewing area where you can see Haystack Rock, Cannon Beach and the smaller sea stacks jutting out of the ocean.

You will need an Oregon State Parks pass, Oregon Pacific Coast Passport, or a $5 day-use pass to park and explore the trails. You can purchase the day pass using the machine at the car park.

Third Stop: Cape Kiwanda

• Driving time: 1 hour 30 mins (106 km/ 66.3 miles)

Now it’s time to head to Pacific City! This area is home to Cape Kiwanda State Natural Area, one of the most beautiful photography spots on the Oregon coast . It’s known for its stunning cliffs, sandy beaches, and rugged beauty. It even has its own version of Cannon Beach’s Haystack Rock which you can see from Pacific City Beach.

There are a lot of amazing places on the way from Cannon Beach to Cape Kiwanda. If you have an extra day I recommend splitting day 2 into two days so you can visit these spots along the way:

• Oswald West State Park
• Elk Flats Trail  

The highlight of Cape Kiwanda is the massive sand dune which separates Pacific City Beach on the south side from McPhillips Beach on the north side. You can climb up to the top for amazing views over both beaches but be warned it is steeper than it looks. Please also pay attention to the signs and do not venture too close to the fragile edges of the cliffs.

If you’re visiting at low tide, you can walk between the sandstone arches on the north side of the cliffs. You can access this area by walking all the way down McPhillips beach towards the sand dune, or by climbing up and over the sand dune from Pacific City Beach. Do not try and access this area when the tide is in as it is incredibly dangerous and you risk getting stranded or caught by sneaker waves. You can check the tide times here .

Fourth Stop: Lakeside (Optional)

• Driving time: 2 hours 44 mins (200 km/ 124 miles)

We really wanted to see the sand dunes on our 7 day Oregon road trip. There are a lot of different sand dunes along the coast but we wanted to see the larger ones which are located further south near Lakeside. If you’re not worried about seeing them you don’t need to drive all the way down to Lakeside. Instead I would stay overnight in Cape Kiwanda. That way, you can take your time driving from Cannon Beach to Cape Kiwanda and explore some of the other stops I mentioned above on day 2 instead.

If you do want to see the John Dellenback Sand Dunes, Lakeside is a good place to stay overnight. The dunes are only open from 7am to 7pm so it’s unlikely you’ll get there in time on day 2 but you’ll be close by for the next day. I recommend stopping en-route and buying some food for breakfast and lunch for day 3. It’s going to be a long day and you’ll want an early start so having things for breakfast will save you a lot of time.

Where to stay in Lakeside

We actually stayed in Winchester Bay as there weren’t many options available but I wouldn’t recommend the place we stayed (Winchester Bay Inn). Instead, I would suggest staying in Lakeside:

• Lakeside Holiday Home: If you’re travelling with a group then this is a great option as it sleeps up to 5 people. It has all the amenities you need including a kitchen, washing machine and dryer, BBQ and Wi-Fi. Check prices > 
• Seadrift Motel & RV Park: This is a good option if you’re travelling with an RV but it is pretty basic. It’s close to the sand dunes and has the essentials. Check prices > 
• Best Western Salbasgeon Inn & Suites: If you prefer hotels, your best option is the Best Western in Reedsport. It’s a bit further away but is still only a 15 minute drive to the sand dunes. Check prices > 

OREGON ROAD TRIP DAY 3: LAKESIDE TO BEND

Get up and have some breakfast while getting ready for another busy day. Once you’ve fuelled up for the day, it’s time to drive to John Dellenback Sand Dunes. From here, you’ll then drive into central Oregon to explore the Willamette National Forest before heading to Bend for the night. If you haven’t already, I suggest stocking up on food and supplies before you drive through Willamette National Forest. Cell service will be very spotty in this area so you probably won’t have signal for part of today’s drive.   

First Stop: John Dellenback Sand Dunes

• Driving time: 5 mins (2.9 km/ 1.8 miles)

The John Dellenback Sand Dunes are located in the Oregon Dunes National Recreation Area. These particular sand dunes are the widest stretch of dunes on the Oregon coast so it’s a very unique outdoor experience. What makes them even more special is that they are closed to motorized vehicles. While other areas of the Oregon Dunes National Recreation Area are open to OHVs, this area isn’t so you can walk on them safely.

The best way to explore the dunes is on the John Dellenback Dunes trail head. It’s a 9km loop which takes you through the sand dunes out to the ocean and back but you don’t have to do the whole trail. We knew we had a long day ahead of us so we just did the first couple of kilometres and then turned back.

You need to pay the $5 day-use fee to park here and hike the trail. Despite reading lots of blog posts that said you had to pay in cash (and rushing around trying to find an ATM), you can pay online using your phone. When you arrive, head to the information board and you’ll see the QR code. You can scan that and then follow instructions to get your day pass. Northwest Forest Passes and Interagency Passes are also accepted.

The trail starts from the parking lot and takes you through the coastal forest. After about half a mile, you’ll emerge from the forest onto the sand dunes. Go left and hike up the large sand dune. From here, you’ll get amazing panoramic views over the dune landscape. You can continue on to the ocean or just stay here and take in the sand formations like we did.

Second Stop: Terwilliger Hot Springs

• Driving time: 2 hours 49 mins (244 km/ 152 miles)

After you’ve finished exploring the sand dunes, it’s time to start the long drive up to Willamette National Forest. I recommend stopping in Eugene (approximately 1 hour 45 mins driving time) to get some lunch and break up the journey.

From Eugene, you’ll take Highway 126 (also known as the McKenzie Highway into the forest. After about 50 minutes, you’ll turn right onto Cougar Dam Road and then right again at the next junction. Keep driving along this road until you reach Cougar Reservoir where the road splits. Go right and keep driving until you reach the parking lot for Terwilliger Springs. This part of the drive can be a bit bumpy so watch out for pot holes.

Terwilliger Hot Springs (also known as Cougar Hot Springs) is a natural hot spring located in the forest. It’s open from sunrise until sundown each day and gets very busy so don’t expect to have this place to yourself unless you’re able to go first thing in the morning! To get to the hot springs, you have to hike an easy 0.5 mile trail through the forest. The entrance fee costs $10 per person for 2 hours and is payable by cash or card at the trailhead which is often manned.

There are a few different hot pools with varying temperatures. The upper pool is the hottest but that makes it the most popular so you may want to try some of the lower pools instead. In the US, hot springs are clothing optional so expect some nudity. Be respectful if you’re taking photos and read up on hot spring etiquette before going.

Third Stop: Koosah and Sahalie Falls

• Driving time: 41 mins (50.8 km/ 31.6 miles)

Once you’ve finished soaking, head back to the car and drive back up to Highway 126. Turn right onto the highway and continue driving for about 25 minutes until you see the sign Sahalie Falls on the left hand side. There is a small parking area along the side of the road. You’ll need to do a U-Turn to park there so just be careful as cars drive quite quickly along this highway.

Sahalie and Koosah are two beautiful waterfalls which are located in the Willamette National Forest. The 2.2 mile Waterfalls Loop trail offers incredible views of both waterfalls, as well as the McKenzie River rushing through the canyons. I don’t think I’ve ever seen such a blue river before! If you don’t want to do the full hike, you can just walk 5 minutes from the car to Sahalie Falls lookout instead.  

The trail is well-maintained but if you’re doing this 7 day Oregon road trip in spring, I would pack some micro-spikes. There is usually a lot of snow in this area and although the trail will be packed down it can be very icy.

Fourth Stop: Bend

• Driving time: 1 hour 8 mins (91.4 km/ 56.8 miles)

Once you’ve finished at the waterfalls, it’s time to drive to Bend. It should take about an hour but you can always stop in the town of Sisters on the way if you need gas, food or a rest break. You’ll probably arrive in the evening so I recommend checking into your hotel and going out for some food. Tomorrow, you’ll have a more relaxing day and will be able to explore Bend properly.

Where to stay in Bend

There are plenty of options to choose from in Bend. Here are a few ones that I’d recommend:

• The Riverhouse on the Deschutes: Located just north of the town centre on the river, the Riverhouse is a great place to stay if you’re visiting Bend and want somewhere peaceful to relax. We stayed here on our 7 day Oregon road trip and I can’t recommend it enough. Check prices >
• Campfire Hotel: This boutique hotel is a great affordable option if you’re travelling on a budget. The rooms have everything you need and there is also an outdoor pool, hot tub and fire pit. If you’re looking for a more sociable atmosphere then this is a good place to stay. C heck prices >
• Springhill Suites Bend: Located in the Old Mill District, Springhill Suites is another great place to stay while visiting Bend. It’s also walking distance to the town centre (15 minutes) so you can easily explore on foot and not worry about driving or parking. Check prices >   

OREGON ROAD TRIP DAY 4: BEND

After a busy few days of driving, today will be a much slower day so you can relax and rest before hitting the road again tomorrow. Known for its outdoor recreation, craft beer scene, and vibrant arts culture, Bend is a great town to explore. It offers ample opportunities for hiking, biking, skiing, and river rafting depending on the time of year you visit. Here are a few fun things to do in Bend:

Explore the town

Bend’s downtown area is bustling with unique shops, art galleries, and local eateries serving up delicious farm-to-table cuisine. Explore the town centre and then wander down to Drake Park and walk along the river. Check out the Old Mill District and grab a coffee from Sisters Coffee.

Try local beers

Bend is known for its microbreweries, making it a popular place for beer lovers. Deschutes Brewery is renowned for its iconic Black Butte Porter and offers tours and tastings. For something a bit different, try Boneyard Beer which has lots of innovative brews. 10 Barrel Brewing Co. is another great spot offering a lively atmosphere and wide selection of beers. Other notable breweries include Silver Moon Brewing and Bend Brewing Co.

Hike up Pilot Butte

This large, cinder cone is visible from almost anywhere in town. Formed over 190,000 years ago from a volcanic eruption, Pilot Butte offers panoramic views of Bend and the surrounding Oregon landscape. It’s a 2 mile round trip and usually takes about an hour to hike there and back. If the weather is on your side, aim to hike up Pilot Butte for sunset and enjoy 360 degree views in golden hour.

Visit Tumalo Falls

Located about 20 miles outside of Bend, Tumalo Falls is a stunning, 89-foot tall waterfall. To get there, take Skyliners Road from Bend and follow the signs. The falls are visible from the parking lot and a short hike will take you down to the base of the falls. For a longer hike, take the Tumalo Falls Trail, a 7.5 mile loop that offers beautiful views of the waterfall and surrounding wilderness. The trail is moderately challenging and you’ll enjoy lush forests, cascading creeks, and panoramic vistas on the way.  

Check out Mount Bachelor

Mount Bachelor is a stratovolcano in the Cascade Range of Central Oregon. In winter, it offers world-class skiing and snowboarding on its expansive slopes. It’s also a great spot for snowshoeing, snow tubing and dog sledding. In summer, the mountain transforms into a playground for hiking and mountain biking.

For more things to do in Bend, check out Visit Bend’s website.

OREGON ROAD TRIP DAY 5: BEND TO HOOD RIVER

Today is going to be quite the adventure! If the weather is nice, get up early, grab some breakfast and head to Smith Rock State Park for a sunrise/ early morning hike. Consider packing some breakfast to eat on the trail and some food for the drive through Mt. Hood as there aren’t a lot of places to stop.

First Stop: Smith Rock State Park

• Driving time: 30 mins (42 km/ 26 miles)

Located just 30 minutes from Bend, Smith Rock State Park is one of the most unique spots on this 7 day Oregon road trip. The park is one of the 7 wonders of Oregon and boasts towering rock formations carved by the Crooked River, creating a dramatic landscape of cliffs and canyons. The park’s unique geology makes it a popular spot for rock climbing and hiking.

Important information about Smith Rock State Park

You need to pay the $5 day-use fee to park here and hike the trail. When you arrive, head to the information board and you’ll find the pay machine.

There are rattlesnakes in some parts of the park, particularly near the river, so keep your eyes peeled. In summer, they will hide under rocks to keep cool so just be mindful. I also recommend reading up on trails before you hike and checking in with the visitor centre as people report snake sightings to them. Seek medical attention immediately if you are bitten.

The best way to experience the park is to do one of the hiking trails. Rim Rock Trail (0.5 miles) is a great easy hiking option and circles the ridge of the park. You’ll get sweeping views and the trail is relatively flat so it’s a good one for kids. Another good option is Canyon Trail (1.5 miles) which takes you down to the river.

If you’re a keen hiker and are up for something more challenging, I highly recommend the Misery Ridge and River Trail (4 miles). It is an uphill grind but it will take you up to Misery Ridge where you’ll get panoramic views over the park and out to the Cascade Mountains. This is a great hike to do for sunrise or sunset depending on when you visit.

Second Stop: Trillium Lake (Seasonal)

• Driving time: 1 hour 44 mins (137 km/ 85.3 miles)

Head north on Highway 97 for about 10 minutes and then merge onto Highway 26. This will take you all the way to Mount Hood National Forest. It’s a beautiful drive through dense forests and towering peaks. Home to the iconic Mount Hood, the highest point in Oregon, this area is a popular spot for hiking, camping, fishing and skiing. On this 7 day Oregon road trip, you’ll only have time to explore Trillium Lake. However, if you have more time you could add on an extra day and explore more of Mount Hood.

Trillium Lake has a beautiful view of Mount Hood and is incredibly picturesque. This is a great place to have lunch and stretch your legs. There are vault toilets and picnic tables. If you feel like it, you can also do the easy 2-mile Trillium Shoreline Look Trail.

If you’re travelling in spring, be aware that the road may not be accessible. When we went in March there was a lot of snow along the highway and it was blocking the entrance down to Trillium Lake. We weren’t able to make it down to the lake even though we had a SUV. Before starting your trip to Mount Hood, check the National Weather Service’s website for up-to-date information on current snow conditions.

Third Stop: Hood River

• Driving time: 59 mins (68 km/ 42.3 miles)

Now it’s time to head north to Hood River! This will be your final destination for the day, but if you’re making good time, feel free to stop at any other points of interest along the way.

Hood River is a picturesque city located on the Columbia River and is renowned for windsurfing, kiteboarding, hiking and mountain biking. Aim to arrive here by late afternoon so that you can explore the area before dinner. The Indian Creek Trail and Hood River Waterfront Trail are both lovely walks. Another great option is Panorama Point. This park is handicapped-accessible. You can drive up to this viewpoint and enjoy panoramic views of Hood River Valley, including Mount Hood and the numerous wineries and orchards.

There are also plenty of vineyards and tasting rooms such as Phelps Creek Vineyards, Cathedral Ridge Winery, and Hood Crest Winery. For a fun evening activity, book a wine and bike tour with MountNbarreL .

If you’re doing this 7 day Oregon road trip in June or July, don’t miss the Hood River Lavender Farms. They grow and produce local and organic lavender products such as essential oils and soaps. The lavender usually blooms in late June and you can pick your own lavender for $10.

Hood River is also home to Mount Hood Railroad . This is one of the best attractions in Hood River for kids and adults alike. You can take the hour-long train ride from downtown into Hood River Valley. It’s a scenic journey through the Columbia River Gorge past orchards and vineyards.

Where to stay in Hood River

Hood River has a range of accommodation options. Here are a few recommendations:

• Hood River Hotel: This historic hotel is one of the oldest spots in Hood River. Located in the centre of downtown, Hood River Hotel is a great base for exploring the local restaurants, breweries and wineries. They’re actually the sister hotel of Campfire Hotel in Bend so you may be able to get a discount if you book both. Check prices >
• Sunset Motel Hood River: This is a great option if you’re travelling on a budget. Sunset Motel Hood River is a bit further from the town but is located close to the highway which makes it an ideal place to stay. Check prices >
• Tucker Park Campground: If you’re looking to camp, Tucker Park Campground is a good option. All campsites at Tucker Park are available on a first-come, first-served basis between May 1 and October 31. The campground is closed between November 1 and April 30. Check prices >

OREGON ROAD TRIP DAY 6: HOOD RIVER TO PORTLAND

You’ll be exploring one of my favourite parts of Oregon today – the Columbia River Gorge. Spanning over 80 miles, Columbia River Gorge serves as a natural boundary between Oregon and Washington. It’s another of Oregon’s 7 wonders and for a good reason! The Columbia River Gorge is home to unique geological features and scenic vistas. With over 90 waterfalls scattered throughout the area, the Gorge is often referred to as the ‘waterfall wonderland of the Pacific Northwest’.

There are so many incredible waterfalls on today’s drive along the I-84. Some are very accessible (viewpoints close to the parking lot) while others require you to hike in. You can stop at as many as you like but here are my suggestions based on our own 7 day Oregon itinerary.

Waterfall permits

If you’re visiting between May and September, you will need a timed permit to visit most of these waterfalls. You can find more information here . 

First Stop: Wahcella Falls

• Driving time: 25 mins (37 km/ 23.3 miles)

This was probably my favourite waterfall in the Columbia River Gorge. The short 1.9 mile out-and-back hike leads you through the lush canyon to the two-tiered waterfall. It’s a fun and scenic hike but it can be quite slippery if there has been a lot of rain so make sure you have shoes with good grip. It costs $5 USD to visit. You can pay online by scanning the QR code once you arrive at the car park.

Second Stop: Multnomah Falls

• Driving time: 11 mins (14.8 km/ 9.2 miles)

Head back onto the Historic Columbia River Highway and drive 10 minutes west to Multnomah Falls. This is one of the most accessible waterfalls in Columbia River Gorge so it can get quite crowded. The parking lot can fill up quickly in the summer months and on weekends so you may have to drive to another waterfall and try again later.

From the car park, cross over the road and the viewing platform is straight ahead of you. This two tiered waterfall is an iconic sight and is the tallest waterfall in Oregon. If you want a different perspective you can hike 0.2 miles up to the Benson Bridge or 1.2 miles to the top of the falls. We decided to just enjoy the view from the main viewing area as we wanted to see quite a few different waterfalls.

Third Stop: Latourell Falls

• Driving time: 12 mins (9.5 km/ 5.9 miles)

The final waterfall on today’s list is Latourell Falls. You can walk down to the base of the waterfall (less than 5 mins) or you can opt to do the 2.4 mile round trip hike to see the upper falls as well. At the base of the waterfall there is a lovely bridge which is great for photos with the waterfall in the background. This particular waterfall can be very busy as it’s one of the closest ones to Portland so be prepared for crowds in the summer and at weekends.

Fourth Stop: Portland

Once you’ve finished exploring the Columbia River Gorge, it’s time to drive back towards Portland. If you’re flying out of Portland, it makes sense to stay here overnight and explore a bit of Portland before you leave. However, if you’re travelling back to Vancouver or Washington, you might want to drive further north and stay closer to Seattle. We decided not to stay in Portland and instead continue up to Olympia for two reasons. Firstly, accommodation was a lot cheaper and secondly, we wanted to shorten the long drive back to Vancouver. It’s completely up to you and will depend on where you’re travelling back to.

Where to stay in Portland

If you decide to stay overnight in Portland, here are a few hotel options:

• The Mark Spencer Hotel: Located in Portland’s Pearl District, this boutique hotel is just steps from all that Downtown Portland has to offer. Check prices >
• Courtyard by Marriott Portland City Center: This hotel is also in the Pearl District. It’s on the pricier side but has fantastic amenities and is also pet friendly. Check prices >
• Econo Lodge City Center: Located further south, this is a great budget option. It’s close to Portland State University and is good value for money. Check prices >

OREGON ROAD TRIP DAY 7: TRAVEL HOME

It’s time to head home! Depending on where you’re travelling back to, you could explore Portland in the morning before your flight home. If you’re driving back to Washington or Vancouver, you could stop in Seattle or explore some beautiful spots in Washington, such as Snohomish, Bellingham or Chuckanut. If you have a few extra days, I highly recommend extending your road trip and visiting Olympic National Park in Washington. With ancient rainforests, rugged coastal beaches, and unique ecosystems, it’s an amazing place to explore.

MORE THINGS TO DO ON AN OREGON ROAD TRIP

This 7 day Oregon road trip will give you a taste of the state’s epic scenery. If you have more time and want to see more of Oregon, you could continue on to some of the below destinations:

• Silver Falls State Park
• Umpqua National Forest (Toketee Falls and Umpqua Hot Springs)
• Samuel H. Boardman State Scenic Corridor
• Crater Lake National Park

PLANNING A 7 DAY OREGON ROAD TRIP: FINAL THOUGHTS

Oregon really does have it all and I can’t wait to go back and explore more of this state. I hope this guide helps you plan your own Oregon road trip. If you have any questions, please drop them in the comments and I’ll do my best to answer them!

Where to explore next?

If you’re looking for more North America travel inspiration, have a look at these guides:

• A complete guide to Capitol Reef National Park
• Exploring Zion and Bryce Canyon: An epic 3-day road trip itinerary
• How to spend a weekend in Bryce Canyon

British Columbia

• 7 Amazing places to visit on Vancouver Island
• North Vancouver Island: An amazing 4-day road trip itinerary
• The ultimate Vancouver to Banff road trip itinerary
• The Best of Banff: The complete 4-day itinerary
• How to explore Banff and Jasper without a car
• Driving the Icefields Parkway: The stops you can’t miss

Love from Steph

Save for later.

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2 thoughts on “how to plan an unforgettable 7 day oregon road trip”.

We wanted to let you know that we took your advice and did this road trip last month. We are a family of 4 from Boston and wanted to see someplace new. We had never explored the Pacific NW. I did a google search and came across your blog post. It looked amazing so I went with it. It was the most amazing trip. We were blown away by all the beauty in Oregon – from the coast to the forest to the desert and all the neat towns in between. What an amazing place! Thank you for all the great tips. We stayed in the hotels you recommended and hit most of your stops. It was so easy to plan – thank you! My family was very impressed by all we were able to see in a week. I never would have been able to plan such an adventure without you. Keep up the traveling and blogging! Where should we go next? All the best, Page

Hi Page, That means so much! Thanks for taking the time to let me know. I did a lot of research before we went as it was our first time exploring that area too so I’m really glad it helped you plan your own trip! I have a lot of guides coming out soon about Quebec and the Canadian Rockies so if you haven’t been there yet, I highly recommend both areas! Best wishes, Steph

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The Perfect 7 Day Oregon Road Trip Itinerary

There’s nothing more iconic than a US road trip and one of the best states to do so (I think) is in Oregon! There are endless Oregon road trip options. You have the rugged coast, lush forests, and torrid deserts—all in one state. Oregon kinda has it all, and unfortunately, you’ll quickly realize a week just isn’t enough. But better to have a taste than nothing at all, right?

There are plenty of adventurous things to do in Oregon to take on but here are some of my favorite areas to explore—so grab your backpack, your car keys, and head on out for this epic 7 day Oregon road trip itinerary.

Things to Know Before Your Oregon Road Trip

Shall I state the obvious? You’ll need a car for your Oregon road trip! If you have one, you’re good to go. Those visiting the USA, here are some things worth noting…

Campervanning the USA is like a religion and honestly, it’s an amazing way to experience the USA. Some well-known companies to rent from are Budget, Escape, Apollo, and Cruise America.

If you don’t want to campervan and just want to rent a car , that’s cool too! Although, do keep in mind that in high season you may want to prebook a hotel and that limits spontaneity on the road since you HAVE to drive to your hotel to sleep. A few popular car rental companies in the USA are: Hertz, Enterprise, and Alamo.

We recommend trying to find the best deal for a rental car by comparing prices and booking your rental car in advance with Expedia.

An alternative to the above is camping . If you want to just rent a car, you can keep costs down and spontaneity alive by camping along your Oregon road trip route. There are plenty of campgrounds in Oregon along the areas I have you going to below! Just bring a tent, sleeping bag, mat, and a cooler and you’re pretty set to go.

Keep in mind driving in the USA takes a long time and Oregon isn’t a small state. Your Oregon road trip itinerary below is pretty crammed because I want you to see A LOT but with that said, you’ll need to add on a couple of driving days, or at least, half days to actually tackle everything below.

Oregon Road Trip Day 1 – Columbia River Gorge

Please don’t skip this area when you’re doing an Oregon road trip! It’s an easy day trip from Portland and is teeming with stunning views and adventure activities.

The Columbia River Gorge is famous for Multnomah Falls , a famous waterfall that’s easily visited just a few steps from the parking lot, but I recommend you continue along the trail so the crowds start to thin and you’ll come across plenty more waterfalls to see.

Here is where there are tons of waterfall hikes near Portland, which makes for an amazing city escape. Make sure to visit the Vista House and maybe do some water sports on the Gorge as well.

Oregon Road Trip Day 2 – Mount Hood

The hikes in Mount Hood are amazing, my favorites are the Tom, Dick, and Harry hike and the hike to Tamanawas Falls.

Both the Columbia River Gorge and Mount Hood areas offer hundreds of miles of hikes near Portland! So if you’re planning on visiting the city, but are in need of a nature fix, there’s no shortage with these two spots just an hour east!

Oregon Road Trip Day 3 & 4 – Bend

There are so many things to do in Bend, it’s a struggle to recommend only a few.

Take a stroll around, or better yet, float the Deschutes River if you’re visiting in summer. It’s pretty much an initiation to the town. Drink all the craft beer at any one of the 30 or so breweries in town and watch the sunset at Pilot Butte.

While Bend is amazing itself, it’s made even better by its close proximity to tons of cool things. For your next day near Bend on your Oregon itinerary, you could do any number of things…

• Summit a mountain like South Sister.
• Play in one of the gorgeous Cascade Lakes—you can rent SUP boards or kayaks at Lava or Elk Lake.
• Visit Smith Rock State Park and go hiking. The popular trail here is Misery Ridge.
• Ride out to Paulina Peak, hike to the top, and then visit the hot spring by the lakes below.

You won’t have time for all of these things I’ve recommended for your time in Bend on your Oregon road trip, so I hope you’re planning your visit back already for Oregon road trip number 2!

Oregon Road Trip Day 5 – Crater Lake

If you only have one day on your Oregon road trip itinerary, I’ll recommend spending the full day at Crater Lake . Aside from it being the coolest lake in Oregon, it’s also the State’s only National Park.

The Watchman’s Peak Trail is less than a two-mile hike and offers great views. If you’re not into hiking, you can drive along the entire rim of the lake for incredible views too.

Oregon Road Trip Day 6 & 7 – Oregon Coast

The amount of incredible views you can get from hiking just a few miles is staggering. The rugged coast is what photographer dreams are made of and the shots here are probably some of the most popular photos you’ve seen of Oregon.

One of the best spots for Oregon photography is the Samuel H. Boardman area . If you’re heading back up north to Portland, stop at Bandon and Cannon Beach along the way to visit a few more iconic coastal towns.

Extra Time on Your Oregon Road Trip Itinerary?

If you have extra time on your Oregon road trip itinerary these are great additions!

Eastern Oregon is often overlooked when visitors come to Oregon. Most head to the coast or hang around Portland but Oregon’s eastern side is STUNNING.

I’m sure many of you think about moody skies, a rugged coast, and snow-capped mountains when you think of Oregon. But did you know there are deserts too?

If you have the time, I can’t hype the eastern side of Oregon enough, here’s a quick rundown on what you can add on to your Oregon road trip itinerary…

John Day Fossil Beds – There are three units here to experience, The Painted Hills are the most famous and deserve a day. The other two, Clarno and Sheep Rock, can be squeezed into another full-on day. Bizarre rock formations, short and sweet hikes with great rewards, and alien landscapes painted in rusty red, golden orange, and dusty yellow await you here.

Alvord Desert – A dried up salt flat that’s 12×7 miles. Here you can whip around a desert in your car, camp for free at night on the playa, and visit the Alvord Hot Springs! You can see the Steens Mountain from here as well that has a scenic drive at the peak as well as a couple of hikes. You could do a large chunk of this area within a full day.

The Wallowas – Deserving of at least two days, there are too many hikes to counque, snow capped peaks to gawk at, and lakes to play on.

Hart Mountain – An Antelope Refuge, desert scrub, and natural hot springs will keep you busy for a day here.

Best Time of Year for an Oregon Road Trip

You might be wondering when the best time to plan your epic Oregon road trip itinerary for.

Spring, summer and, fall are all great times and winter could be an option as well if you’re wanting some snowy adventures and have the right vehicle.

Summers will pose more crowds though, as it’s the most popular time to road trip and explore the state. To get a bit of relief from the masses, try coming around April, May and, October.

Those are just outside the busy months, so you may score cheaper deals on the rental car, and the weather will still be nice!

Oregon Road Trip Tips

You’re on a road trip, so remember to pack efficiently and only what you need so you don’t have a mess in the car.

If you’re looking to save money, camping in Oregon is really easy and very cheap – a great way to save money on your Oregon road trip.

Don’t forget driving around the State will take time. It’s best to start really early in the morning to get the most out of your day and journey on your Oregon road trip itinerary. You’ll struggle to see everything I laid out here in this post but I wanted to give you some options! 

You will have to add on a few days to complete this 7 day Oregon road trip itinerary above or slice off a day as the drive-in between spots will take a decent chunk out of each day.

Driving a night is discouraged . If you’re riding into the city past dark, that’s probably fine but if you’re pretty out there you risk getting in an accident with wildlife. They love to come out and play after dark so be on high alert if you’re caught out driving at night.

Many of Oregon’s parks require a pass. Crater Lake is a national park which requires its own pass, and the Northwest pass (used in Washington and Oregon) is used for most other areas. If you don’t get this pass, you’ll pay a $5 day fee but after a few of those, and if you’re continuing on to Washington, you mine as well pay for the year pass! See where you’re going and what makes the most sense to you.

For winter, you may need a snopark pass depending on where you go! Read up so you don’t get caught with a fine.

I hope this helped you plan your Oregon road trip around this amazing state!

About the Author

Oregon is for Adventure is ran by two Oregon lovers, one native (Garrett), the other, a convert from Florida (Nina). Both are full-time travelers but Oregon reels them back in each year for a visit. Oregon is for Adventure is an amazing resource for those visiting Oregon wanting real adventures and valuable advice from locals/experts on Oregon.

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Planning more travel around the PNW? Check out our incredible guides to Seattle including unique things to do in Seattle and amazing Seattle day trips ! And check out more awesome day trips from Portland for more ideas!

Enjoyed this guide on the perfect 7 day Oregon road trip itinerary or found it helpful? Bookmark for later or share the love below on Pinterest!

Megan loves cats, pizza, and finding cool themed bars and hotels in New York and on her travels!

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Home » North America » USA » Oregon

Epic Oregon Road Trip Travel Guide | Best Routes in 2024!

Going on a  road trip in Oregon  has to be one of the best ways to experience the state! With your own car and the freedom of the road, you’ll be able to go wherever you want and see whatever you like in this glorious state.

Oregon is a magical place full of beautiful landscapes, interesting people, and amazing food and drink. There are few other destinations in the world where you can surf and ski in the same day and, for that matter, drink some of the best beer of your life all the while.

There’s a lot to do in Oregon but, make no mistake, this is a big, wide-open state, one that requires plenty of time and patience to see.

Renting a car in a foreign state or country can be intimidating. Travelers may not know where to go or what to do. They may be worried about expenses or spending too much money pointlessly as well.

Don’t worry – we have the insider information you need for an EPIC Oregon road trip.

Written by a road-trip expert and local, this epic guide covers everything you need to know about visiting Oregon by car or campervan.

We’ll show you exactly how to stick to a budget, tell you about the best things in Oregon, and give you plenty of ideas and itineraries so you can easily plan out your entire trip!

So let’s start planning your dream Oregon road trip!

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Oregon Road Trips Costs

Best road trip in oregon.

• The Oregon Coast

The Cascades Itinerary

Eastern oregon road trip, the grand tour oregon itinerary, places to visit in oregon, oregon road trip tips, apartments and hotels in oregon, renting a car or campervan in oregon.

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Oregon is about average when it comes to the costs of living, though it is quickly becoming one of the more expensive states. A road trip in Oregon can be affordable or it could be expensive – it all depends on how you want to do it.

We at The Broke Backpacker always try to go on affordable adventures and are always looking for ways to travel cheap ! Even if we are unable to travel for $10/day, as we do in our favorite countries, we can at least help you reduce the prices of an Oregon road trip.

The average daily budget for an Oregon road trip is between $150-$200 – this includes gas, a rental car, lodging, food, drink, and entry into certain attractions. Make note of this number but please do not let it discourage you – we’re going to show how to reduce it to a more budget-friendly amount soon.

Gas will undoubtedly be your largest expense while on a road trip in Oregon. It’s sometimes hard to predict how much gas you will use but it is almost always is more than you expect. Do not take this expense lightly and do you everything you can to limit it.

Other than gas, the costs associated with a road trip in Oregon really come down to how you want to travel, eat, sleep, and drink. These run gamut from driving in a cheap economy car to a gas-guzzling SUV and eating out in expensive restaurants to cooking your own food at a campground.

If you are mostly cooking for yourself, camping, and exploring Oregon’s wild places, you can reduce that cost in half. Traveling with at least one other person will also keep costs much lower.

Think about what you want to do on your Oregon road trip route and then set a budget.

Below is a breakdown of the average costs of a road trip in Oregon.

The Broke Backpacker is supported by you . Clicking through our links may earn us a small affiliate commission, and that's what allows us to keep producing free content 🙂 Learn more .

Average Costs of an Oregon Road Trip

Rental car :  $30-$100

RV rental :  $100-$300

Gallon of gas:  $3.23

Private AirBnB home:  $80

Hotel room:  $120

Hostel:  $25-$30

Campground:  $5-$15 (sometimes free!)

Sandwich:  $6-$9

Beer at a bar:  $5-$7

Coffee:  $2-$3

Bottle of Whiskey from market:  $20

Dinner for two:  $30-$50

• The Oregon Coast – 4 days
• The Cascades – 7 days
• Eastern Oregon  – 10 days
• The Grand Tour Oregon – 14 days

Below is a list of sample Oregon road trip routes. Varying from 5 to 14 days in length, they cover many of the top destinations in Oregon. Each itinerary provides day-by-day highlights, which are meant to give you some good Oregon road trip ideas.

The USA is  blisteringly beautiful. It’s also blisteringly expensive! Visiting two national parks in day can run you $70+ in entry fees.

Orrrr… you kick those entry fees to the curb, buy an annual ‘America the Beautiful Pass’ for $79.99,  and get unlimited access to ALL 2000+ federally managed sites in the States totally FREE!

You do the math. 😉

The Oregon Coast is probably the most beloved road trip in the entire state and is a popular area for a holiday stay with both locals and out-of-towners. People flock here to get away from the rat race for a little while and tend to just laze about on the beach or in a local diner.

The Oregon Coast itself is not well-known for its warm weather or clear days, but rather its rugged beauty. Dramatic cliffs, tide pools, and sea stacks are the most notable landmarks here – palm trees are markedly absent.

The best part about a road trip on Oregon Highway 101 is that you’ll never be far away from the coast. This route hugs the near entirety of the shoreline and only deviates when passing through an epic forest. For 90% of the way, it’ll just be you and the ocean.

• Bandon by the Sea
• Samuel H Boardman Park
• Ecola State Park
• Cape Perpetua
• Florence Sand Dunes
• Pacific City Camping Resort Yurts
• Windermere on the Beach  (Bandon)
• Ecola Creek Lodge  (Cannon Beach)
• Norblad Hotel  (Astoria)
• McMenamins Gearhart Hotel  (Gearhart)
• Shucking fresh oysters
• Bonfires on the beach
• Surfing at Oswald West
• Whale watching

The entire way.

• Pelican Brewery (Cape Kiwanda)
• The Schooner (Netarts)
• Fort George Brewery (Astoria)
• Local Ocean Seafoods (Newport)
• Mattie’s (Brooking)
• Festival of the Dark Arts in Astoria (February)
• Goonies Day in Astoria (June)
• Newport Seafood and Wine Fest (February)
• South Coast Clambake and Jazz Fest (March)
• Southern Oregon Kite Festival (July)

Oregon’s Cascade Range is not the highest nor the most epic in the USA – these mountains are fairly gentle and draw attention only when there is a volcano around. Hidden in the lush fur of these slopes though are, hands-down, the best waterfalls in the country, not to mention some of the most beautiful lakes in the world. Better yet, some of Oregon’s best cabins and treehouses are found here, so book a stay amongst the forests for a once-in-a-lifetime experience!

Mt Hood and Crater Lake are the Cascade’s most famous landmarks and both are must see places in Oregon. In between these two are countless more treasures, including, but not limited to, Jefferson Park, Marion Falls, Clear Lake, and the Three Sisters Wilderness. I’m barely scratching the surface as well.

Following a road trip in the Cascades, you will also have the chance to drive up the Willamette Valley, which has some of the finest Pinot Noirs in the world. Nothing really beats a glass of wine or a B&B at a vineyard after spending a week in the mountains.

• Crater Lake
• Columbia River Gorge
• Willamette Valley vineyards
• Lots of waterfalls
• Maverick Inn  (Klamath Falls)
• Pacific Crest Trailhouse  (Cascade Locks)
• Eugene Whitaker House
• Bunk + Brews Historic Lucas House  (Bend)
• Hiking/skiing at Mt Hood
• Rock climbing at Smith Rock
• Swimming at Crater Lake
• Willamette Valley wine tours
• Waterfall photography
• Crater Lake Rim Road
• Highway 138
• Crux Fermentation Science (Bend)
• Sam Bond’s Garage (Eugene)
• Caspian Cafe (Eugene)
• The Painted Lady (McMinnville)
• Ritter’s Housemade Foods (Salem)
• Oregon Country Fair (July)
• International Pinot Noir Celebration (July)
• Wooden Shoe Tulip Festival (April/March)
• Tigard Festival of Balloons (June)
• Bend Brew Festival (August)

If you need more recommendations on where to stay on your road trip, check out these cottages in Oregon .

A new country, a new contract, a new piece of plastic – booooring. Instead, buy an eSIM!

An eSIM works just like an app: you buy it, you download it, and BOOM! You’re connected the minute you land. It’s that easy.

Is your phone eSIM ready? Read about how e-Sims work or click below to see one of the top eSIM providers on the market and  ditch the plastic .

A visit to Eastern Oregon will be a wholly unique experience compared to the Western portion of the state. Deciduous rainforests and beaches are swapped for desert-scapes and hazy mountains. If you wanted to see a side of Oregon that few are even aware, this is the one.

There are lots of things to do in Eastern Oregon. Smith Rock offers some of the best climbing in the country while the Wallowas (AKA the Oregon Alps) offer some of the best skiing and hiking in Colorado . Steens Mountain and the Alvord Desert are two of the greatest hidden gems on the West Coast and are known only to adventurous Oregonians.

The culture is also distinct from the rest of the state. Cowboys, whiskey guzzlers, social pariahs; all of these are the types of people you’ll see in Eastern Oregon.

• Painted Hills
• Steens Mountains
• Hell’s Canyon
• Dreamer’s Lodge  (John Day)
• Eagle Cap Chalets  (Joseph)
• Rory and Ryan Inn  (Burns)
• Brewery tours in Bend
• Snowboarding at Mt Bachelor
• Hiking in Wallowas
• Desert scenery
• Cowboys in Pendleton
• Steens Mountain Road
• Scenic Lakes Byway
• Deschutes Brewing (Bend)
• McKay Cottage (Bend)
• Roosters Country Kitchen (Pendleton)
• Arrowhead Chocolates (Joseph)
• Sisters Folk Festival (September)
• Deschutes County Fair (August)
• Pendleton Whiskey Music Fest (July)

This the best road trip in Oregon – hands-down. Hell, this is one of the best drives in the USA ! You see everything and then some! The coast, the Cascades, the deserts of Eastern Oregon; all of these areas will be available to you with this itinerary.

In addition to the grand majority of the locations listed above, you will also have more time in Southern Oregon. This region is one of the most neglected parts of the state, which is unfair considering what it offers. The river rafting is epic, Ashland is one of the most charming cities you’ve never heard of, and the wine is arguably even better than that of the Willamette Valley.

So if you have time to kill and want to see the best of Oregon, look no further than this route. Oregon is beautiful and this is the best way to see it.

• Eastern Oregon
• Timberline Lodge
• Traveler’s House  (Portland)
• The Ashland Hostel
• Columbia Hotel  (Ashland)
• Everywhere else mentioned prior
• Skiing at Mt Hood
• Climbing at Smith Rock
• Rafting in Southern Oregon
• Chilling in Ashland
• Wine and beer tours
• Seafood on the coast
• Hiking in the Wallowas
• Growler’s Taproom (Portland)
• Shalom Y’all (Portland)
• Cartopia (Portland)
• Brother’s Restaurant (Ashland)
• Cafe Broder (Portland
• Everything else mentioned in this guide
• Ashland Shakespeare Festival (February)
• Portland Brewer’s Festival (July)
• Portland Rose Festival and Parade (May/June)
• Portland Waterfront Blue’s Festival (July)
• Pickathon (August)
• Portland MFNW (August)

Below is a list of the best road trip stops in Oregon. Study them well and decide which ones you like the most.

Want to save money on accommodation?

We got you. For reals.

Road Trip to Portland

The City of Roses. Little Beirut. Rip City. Bridgetown. Stumptown. Call it what you will but few names can actually capture the intangible flavor and uniqueness that Portland excludes in abundance.

For years, Portland was a city of obscurity, full of eccentrics and abject people. For residents, this anonymity was an ideal situation that allowed them to cultivate their weirdness. Portland has only been “discovered” in recent years by the rest of the world and has since developed into a full-on tourist destination.

Portland is not a big city by American standards. There are no large attractions in Portland like a Hollywood Sign or Liberty Bell. Life is simpler (and better) in Portland because people care mostly about good food, good beer, and good health (both physically and spiritually). For these reasons, the best things to do in Portland are to just eat, drink, and go for a walk.

The best districts in Portland to walk around are definitely the Alphabet District , the Pearl, Alberta Arts , Hawthorne , and Laurelhurst . Other neighborhoods like Belmont, Mississippi, Division, and Chinatown are also worth visiting. On either side of the Willamette River are the Eastbank Esplanade and Tom McCall Waterfront , which are both great places to wander around.

A hike through the lush Forest Park makes for a lovely day. Inside and on the outskirts of the large park are some of Portland’s best attractions like Pittock Mansion , the Rose Gardens , and Japanese Gardens .

If there were must-see landmarks in Portland then they’d probably the bridges. Portlandians are in love with their bridges and take great pride in them. St. John’s Bridge is a crowd favorite as is the iron Hawthorne Bridge.

I’d go into more detail on the city, and talk about the many restaurants and bars, but, unfortunately, there is not enough time and space available in this guide. That’s what the our Portland Budget Travel guide is for – blessings!

  And the  coolest places in Portland to go .

  Craft a killer  Portland travel itinerary .

  Read about the  coolest hostels in Portland .

  And book a killer  Airbnb Portland apartment .

Road Trip through the Columbia River Gorge

With endless outdoor opportunities, the much loved Columbia River Gorge is like a playground for adults! Those looking for the best hikes near Portland should head directly to this scenic area. Also, there are some excellent breweries nearby offering crucial post-hike beers.

Starting in Troutdale and driving along the  Historic Columbia River Highway , you’ll first arrive at the Portland Women’s Forum , which has one of the most iconic views of the Gorge. You’ll see the Vista House perched on the walls of the gorge in the distance as well as the Columbia River .

From there you can continue on to picturesque Laurotell Falls and Bridal Veil Falls (see if you can find the elusive Upper Bridal Veil Fall ). Nearby Angel’s Rest is a very popular sunset hike for locals as well.

The next stop is Multnomah Falls, which is arguably the most spectacular waterfall in Oregon. This near-perfect waterfall drops over 500 ft amidst verdant foliage and is one of the most photographed places in Oregon. In front of the falls is an equally photogenic bridge, which makes the scene look like Rivendell.

Beyond Multnomah Falls, you’ll pass by many other superlative portions of the Gorge, notably Oneonta Gorge and Eagle Creek . These are some of the most beautiful places in Oregon as well as the most crowded. Note that this part of the Gorge was damaged recently by a wildfire and that some trails may be closed.

Past Eagle Creek is Cascade Locks, home to the historical Bridge of the Gods, which is where the PCT crosses into Washington. Further along is the Hood River, which is one of the coolest towns in Oregon. Here are, hands-down, some of the best breweries in Oregon in addition to some killer windsurfing and gorgeous views of Mt Hood and Mt Adams.

Road Trip to Mt Hood

Oregon’s pride and joy, the image that most Oregonians can recall from their earliest memories, is Mt Hood. For outdoor enthusiasts and mountain lovers, Mt Hood will be the crowning achievement on their road trip in Oregon.

Getting to Mt Hood is very easy as one of the states main arteries ( Highway 26 ) runs literally right next to it. The drive is gorgeous and a little perilous if you’re visiting Mt Hood in the winter.

If your car is not able to drive in the snow, which is very common beyond December, you can still catch a local shuttle in Sandy to the main alpine settlements: Government Camp and Timberline , the latter of which is famous for appearing in Stanley Kubrik’s The Shining .

Along 26 are several stops that you should absolutely make time for. Trillium Lake and Mirror Lake are local favorites, however, it’s also one of the most famous hikes in the USA , so the trails can be quite crowded.

There are several awesome spots on the eastern and northern flanks of Mt Hood that can be accessed by several forest roads. Cloud Cap , Tamanawas Falls , and Lost Lake are great places to check out.

If you’re a skier, then Mt Hood is unquestionably one of the best places in Oregon to visit in the winter. The skiing here is world-class and runs come in many forms, from tended to the backcountry. If you’re visiting Oregon in the summer, no worries; Timberline Lodge has the longest ski season in the country and is open 365 days a year.

Mt Hood is one of the most climbed glaciated mountains on the planet, second only to Mt Fuji. It is a great introductory peak for beginners and requires only a long day to summit. You will still need the proper adventure equipment to climb in as well as current condition reports.

Oregon Coast Road Trip

The Oregon Coast is not the typical kind of beach getaway – it’s not warm, it’s not very comfortable, and it’s not at all like those tropical postcards.

oRainy, rugged, and utterly romantic, the Oregon Coast is a marvel in its own way. If you’re travelling the USA for the adventure and appreciate a harsher beauty(or possibly like to wear both sandals and sweaters at the same time), you will instantly fall in love with this place.

The Coast is long and nearly 100% accessible via the Oregon Coast Highway 101 . A road trip on this highway will give you tons of opportunities to experience the local attractions. The Oregon Coast can roughly be divided into three parts (North, Central, and South) and between the three, there are, honestly, too many things to see and do.

Starting north you have the top weekend getaways for Portlandians – Astoria, Seaside, Cannon Beach, and Manzanita. Astoria is mostly famous for being the setting for Steven Spielberg’s The Goonies.

Seaside is a cute town popular with families and is a bit touristy. Cannon Beach is equally as touristy but hosts the stunning Haystack Rock.

Manzanita is the most laidback of the bunch and is aw great base for day trips to Oswald West State Park and Neahkahnie Mountain , both of which offer some of the best Oregon Coast hikes.

Moving south we head past Tillamook , the cheese capital of Oregon, and past Cape Kiwanda, one of my favorite places in Oregon, before arriving in Newport , famous for the highly-regarded Oregon Coast Aquarium . Beyond Newport is ultra-rugged Cape Perpetua , home to the Devil’s Churn, Thor’s Well, and Sea Lion Caves.

After Perpetua, we drive to Florence and the epic Oregon Sand Dunes , which originally inspired Frank Herbert to write the sci-fi masterpiece, Dune . Quad biking on the dunes is one of the most popular things to do on the Oregon Coast, though there are plenty of other places to go for a nice walk.

Saving the best for last, we wrap our Oregon Coast road trip in the south. The stretch between Bandon and Brookings is superlative with state parks like Face Rock, Samuel H. Boardman, and Pistol River all providing amazing settings. Some of the best hikes on the Oregon Coast are also around Boardman.

Willamette Valley Road Trip

The Willamette Valley is the breadbasket of Oregon and the source of much of its delicious produce. It also hosts some of the most respected wineries in the USA, which produce some of the finest Pinots in the entire world, not to mention a number of interesting towns and natural attractions.

The Willamette Valley runs for about 150 miles from Portland south to Eugene . The largest highway in Oregon, Interstate 5 , runs through the Willamette Valley meaning you can travel by car to California .

I5 itself doesn’t really have a lot of great views and the drive itself is pretty boring. Deviate slightly from I5 and there’s lots more though.

There are over 500 wineries spread throughout the Willamette Valley. The greatest concentration of wineries is around Highway 18 near McMinnville, Salem, and Newberg . You could easily spend an entire day touring these vineyards and trying some of the best wine in the country but please remember to drive safely.

To the west of the Willamette Valley, you’ll the see the Cascade Range rising. The Cascades, running all the way from Washington to California, are like the geographic spine of the state and heavily influence the weather.

Hidden inside of the Cascades are some more great waterfalls, which make for great day hikes close to Portland.

Silver Falls State Park is one of the most popular places to visit in Oregon because it offers great scenery and easy trails. Nearby is the much more intimate albeit difficult Abiqua Falls , which has become a local favorite.

Penetrate even deeper into the Cascades and you’ll find hidden gems like Olallie Lake, Bagby Hot Springs, Jefferson Park, Marion Falls, and Three Fingered Jack.

Eugene is worth dropping by if you have a moment. Eugene was once considered the “hippie capital” of Oregon though it’s more gentrified now. You can still get a taste of the counterculture in the bluesy Whitaker District.

Road Trip to Bend

Located on the other side of the Cascades in the High Oregon Desert, Bend is, in a lot of ways, like a foil to Portland. Bend is smaller, more rural, more politically conservative, and even more laid back than “big city” Portland.

Bend still has that quintessential Oregon charm though and ultimately makes for an awesome stop on any Oregon road trip route.

You’ll have to cross the Cascades in order to arrive in Bend. You can cross the Cascades via several passes and each offers their own set of attractions. I personally enjoy driving along Highway 20/126 because I have a chance to visit some of my favorite places in Oregon including Koosah Falls, Clear Lake, Tamolitch Falls, Proxy Falls, and Linton Falls . Note that only the larger highways like 26 may be open in winter.

Bend mostly gets attention for the surrounding landscape, which you’ll be introduced to on the drive in. The city itself is really cool though and actually a really fun place in Oregon to hang in, so it’s definitely worth staying in Bend for a couple nights. If you need ideas for places to stay in Bend, consider checking out one of the incredible vacation rentals . The local breweries, like Deschutes and Crux , are some of the finest in the state and the food ain’t bad either.

People usually head outdoors immediately upon arriving in Bend. Around the city are some of the best mountain biking, skiing, climbing, and hiking in Oregon, making the area a paradise for outdoors people.

Nearby Mt Bachelor is one of the best places to visit in Oregon in winter as the snow is legendary. North of Bend is the holy Smith Rock , which is often considered the birthplace of American rock climbing. East is endless sagebrush.

I definitely suggest driving on the Cascades Lakes Byway in the summer. You can visit local favorites like Tumalo Falls and Sparks Lake , all the while being afforded views of the Three Sisters . South Sister is a popular and relatively easy climb.

Road Trip to Crater Lake

Oregon only has one national park but it is easily one of the most stunning parks in the USA . Crater Lake is a marvel, an enormous body of water held high in the air on top of a collapsed volcano. The water is one of the deepest shades of blue that you will ever see and, officially, some of the clearest. There’s simply nothing else like it in the world.

Crater Lake is located a couple hours south of Bend in the Cascade Mountains. There are several entrances to the park but only one, Munson Valley via Highway 62 , is open (sometimes) in the winter. You’ll have to pay to enter the park though rates change depending on the time of year (summer: $25 winter: $15).

There is a lot to do at Crater Lake, though most people just stand there and stare in awe at it. You can hike, climb to one of the many surrounding peaks, descend down to the lake’s edge for a very cold swim, or simply drive around the rim in the summer on the Rim Road.

Several times in the year the road is closed to vehicular traffic so that bikers and pedestrians may enjoy the park without being disturbed, which is a really nice touch.

Though there is more to do in the summer, the best time of year to visit Crater Lake is in the winter. During this time, there are very few people, tons of snow, and just a powerful stillness to the place. The silence in the winter is almost total and you’ll be shocked, maybe even scared at how serene it is.

You can, of course, camp at Crater Lake though campgrounds can fill really quick. If you strike out camping, the nearest large town is Klamath Falls and it has plenty of lodging.

An Eastern Oregon road trip is a must for anyone who wants to get the full Oregonian experience. Some of the USA’s most beautiful places are found in this part of the state and anyone interested in a more rugged adventure will enjoy Eastern Oregon very much.

A lot of people often imagine Oregon covered in trees and being rained on 24/7; few realize that almost two-thirds of the state is actually a mix of desert terrain and stark mountains.

Lying on the other side of the Cascades, Eastern Oregon is, contrary to the common image, arid, hot, and sometimes bitterly cold. This austere landscape is gorgeous though and only solidifies Oregon as one of the most geographically diverse states in the USA.

The most popular place in Eastern Oregon is probably the kaleidoscopic Painted Hills , located in the John Day Fossil Beds . These hills are a geologic wonder and famous for their bright colors.

Surrounding the John Day area are the Ochoco, Malheur, and Umatilla forests as well as the Blue Mountains and Strawberry Mountains . Fun fact: the Blue Mountains are home to the world’s largest organism – a 2400-year-old fungus that covers over 2,000 acres.

In the far northeastern corner of the state are the Wallowa Mountains aka “The Alps of Oregon.” The Wallowas are an outdoor wonderland that offer great skiing opportunities and some of the best hikes in Oregon.

Most of the Wallowa Mountains fall within the Eagle Cap Wilderness though local townships like Joseph and Enterprise are worth visiting as well.

Nearby to the Wallowas is the historically significant Snake River and Hell’s Canyon , the deepest canyon in the entire United States.

There are many more hidden parts in Eastern Oregon that are really out in the middle of nowhere. To learn more about some of these remote locations among others, refer to the section below where we talk about secret Oregon.

Wanna know how to pack like a pro? Well for a start you need the right gear….

These are packing cubes for the globetrotters and compression sacks for the  real adventurers – these babies are a traveller’s best kept secret. They organise yo’ packing and minimise volume too so you can pack MORE.

Or, y’know… you can stick to just chucking it all in your backpack…

Off The Beaten Path Oregon Road Trip Ideas

Oregon has so many hidden treasures for you to discover! To see something different, start with these relatively unknown locations, which are among the most uniques places to visit in Oregon.

1. Steens Mountains

The epitome of off-the-beaten-path in Oregon; these mountains are located in the far southeastern corner of the state and it takes a real journey to get here. Drive to the top of the mountains via the astounding Steens Mountain Road .

Be on the lookout for wild horses and, in the autumn, the golden aspens. On the other side of the Steens is the Alvord Desert – a surreal playa that is popular among both artists and off-roaders who like to go for joy rides.

2. Owyhee Canyonlands

One of the last untouched desert frontiers in America, full of hoodoos, stone towers, and delicate ravines. The Owyhee Canyonlands are often compared to the national parks and landscapes of Utah  albeit not as extensive.

Popular among hikers, rock climbers, and river rafters though not many people actually make it out this far due to rough and remote roads. Definitely one of the most beautiful and unique places to visit in Oregon.

3. Southern Oregon Road Trip

Though not exactly hidden, Southern Oregon often receives far less attention than the rest of the state. People usually visit to attend the famous Shakespeare Festival in charming Ashland or when passing through on a road trip from California, but there is a lot more happening than most are aware of.

The Rogue Valley has a burgeoning wine and beer scene that will soon rival the Willamette Valley. In terms of natural attractions, there is the Rogue River with its world-class rapids as well as the rugged Siskiyou Mountains and Oregon Caves , all of which make for great adventures.

Oregon Roadside Attractions

Americans have a weird affinity to the strange landmarks that are usually found out in the middle of nowhere. The roadside attractions in Oregon have become so admired that many people go on a trip just see them!

Below is a list of some of the most interesting roadside attractions in Oregon. Did we mention that a lot of these stops are among the best cheap things to do in Oregon as well?

• Peace Candle of the World (Scappoose) – A former silo that was filled with wax and painted red to resemble a giant candle. Promotes world peace.
• Enchanted Forest (Salem) – An amusement park filled with fairytale-themed rides and attractions. Whimsical and a little creepy.
• The Oregon Vortex (Gold Hill) – Place where the laws of physics are purportedly non-existent due to paranormal activity.
• Short Bridge Ghost Town (Short Bridge) – A seemingly derelict town that is actually a very well designed prop.
• Octopus Tree (Tillamook) – An old spruce tree that came to be shaped like an octopus by unknown means.
• Prehistoric Gardens (Port Orford) – A series of lifesize dinosaur recreations in the coastal rainforest. Intended to look like a prehistoric zoo.
• Peterson Rock Garden (Redmond) – An estate full intricate statues and structures made from rocks and stones.
• Oregon Corndog (Rockaway Beach) – Home to the world’s largest (artificial) corn dog. There’s also a bucking mechanical corn dog ride complete with a saddle.
• Evergreen Aviation and Space Museum (McMinnville) – Holy ground for anyone interest in aviation. Hosts a large collection of planes, most importantly the Spruce Goose, one of the largest planes ever designed.
• Oregon State Hospital Museum of Mental Health (Salem) – A real mental institution that was used for filming One Flew Over the Cuckoo’s Nest. Now displays important artifacts from the movie as well as archaic therapeutic techniques.

Oregon Scenic Drives

Everywhere you look in Oregon, there’s beauty; much of it can be seen from the seat of your car! Those who want a glimpse of the state’s splendor from behind the wheel should definitely check out these scenic drives in Oregon.

• Highway 101 – A road trip on Oregon Highway 101 is a great way to experience the best of the Oregon Coast. Most of the Oregon coast’s top attractions are within a stone’s throw from the highway as well. Highlights include the views from the slope of Neahkahnie Mountain, driving past the Oregon Dunes , and seeing the sea stacks of Bandon and/or Cannon Beach . This highway also makes for a natural transition when road tripping from California as the 101 runs all the way up the West Coast to Washington .
• Interstate 84 – Drive through one of Oregon’s greatest points of pride: the Columbia River Gorge. With high walls and dense woods, the Gorge is like something out of Scandinavia. Aside from being gorgeous by itself, the Gorge has lots of hiking opportunities as well as some of the best waterfalls in Oregon.
• Highway 138 – One of my favorite scenic drives in Oregon. Depart from Crater Lake and head northwest through the Cascade Range. Along the way, you’ll have the opportunity to visit some of the prettiest and most unique places in Oregon, including Mt. Thielsen (aka the Lightning Bolt) and Toketee Falls . 138 eventually enters the Umpqua River Valley, which is equally remarkable.
• Highway 26 – A great commute that affords road trippers glimpses of the tableau that is the Oregonian landscape. On this scenic drive through Oregon, you’ll have the chance to experience the state’s amazing geographic diversity. Start on the coast (Cannon Beach) and drive east through the city of Portland, the alpine forests at the base of Mt. Hood, and then down to the Oregon High Desert. 26 goes all the way to Boise, Idaho but the Painted Hills are a great place to stop.

Why Visit this Part of the World

Oregon is one of the brightest and quirkiest places in all of the USA. It is a spectacular state that provides everything that makes for an awesome road trip: great food, gorgeous natural attractions, engaging people, and best of all, an easygoing culture that loves to enjoy itself.

Due to its relative isolation, Oregon has always been a hideaway for the abject in society, which has shaped both its history and demographgics for better or worse .

In short, many people – the eccentric, unaccepted, burnt-out, adventurous sorts – who felt confined in conventional American life all fled to the farthest corner of the US, that is the Pacific Northwest . The result of this migration is now an established culture that champions the strange and alternative.

Oregonians are very proud of their eccentricities. You’ll often see people in the cities of Portland and Eugene doing, saying, and wearing whatever they want, sometimes to a bombastic level.

Libertarianism and separatism are very popular concepts in Oregon, both among urban and rural centers. Regardless of politics though, Oregonians are very outspoken people.

And why shouldn’t they be outspoken? Oregon has some of the most fantastic landscapes in the USA, a mostly forward-thinking society, and a people that really give a shit. Quality, ecologically-friendly products are of the utmost importance here and social progressivism is often at the forefront of people’s lives here.

There are very few places as interesting or as enthralling as Oregon. Between the hugely varied landscapes and the larger-than-life personalities, this is a state that grips you and doesn’t let go. It plants a seed and takes root in everyone’s mind and everyone has a hard time ending an Oregon road trip.

Getting Insured

Traveling without insurance would be risky so do consider getting good backpacker insurance sorted before you head off on an adventure.

ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing .

They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.

SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!

Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.

Top Tips for Broke Backpackers

Below is a list of Oregon road trip ideas for saving money. Try and practice these as much as possible.

• Rent an economy car: Prices can be as low as $25/day depending on the time of year and how far in advance you reserve. Economy cars are also more fuel efficient so you’ll save on fuel. Use apps like ViaMichelin to find cheap gas, which, seriously, always ends up being one of the most surprising and costly expenses on a road trip.
• Use vehicle relocation services: These brilliant services offer huge discounts to people on the condition they get a vehicle to a certain place at a certain time. No joke, you can rent a car sometimes for as low as $1/day! Availability is very limited though, so keep a watchful eye on the sites. Check immova and Cruise America to start with.
• Sleep overnight in an empty lot: Though not technically legal in Oregon, people sleep in parking lots all the time. Make sure the lot is safe by asking around. Walmarts are reportedly good places to park overnight as they allow overnight parking.
• Camp: Unless you want to fork out big bucks for a lodge, pack the car with your camping essentials . Campgrounds are way less expensive and sometimes even free.
• Cook your own food: Eating out can be very expensive in Oregon. Cook your own food as much as possible to save – I recommend bringing a portable backpacking stove. Otherwise, have a fancy night out at a food cart.
• Do free shit: There are lots of free things to do in Oregon! From hiking to laying on the beach to going to the local monuments; all of these things cost you nill. You can get started with this awesome guide to free activities in Portland from OregonLive. Be sure to keep your ear to the ground for all things free in Oregon.
• Pack a travel water bottle: It’s good for your wallet and the environment.

Sometimes you need a roof over your head and your own shower to clean all that grime away from camping. Luckily, there are a whole range of accommodation types in Oregon catered to all sorts of travelers.

It might be a good road trip idea in Oregon to stay at a lodge once or twice for a recharge. Sticking to a budget while not staying in a dump will still require a bit of research.

There are plenty of budget hotels and motels in Oregon but they suffer from a drab and uninspired design that is endemic to most cheap American lodging.

You can check into a cheap hotel in Oregon for a night, and will often have to, but don’t expect much. At more than $60/night minimum, staying in these cheap hotels can start to feel like a waste very quickly.

Although the USA’s hostel scene is lacking outside the major backpacking destinations, you can find hostels in Oregon that are affordable and fun.

AirBnBs in Oregon are often cheaper and far more intimate than generic hotels. There are some really crazy AirBnB rentals out there as well! I’ve seen yurts, teepees, tree houses, renovated barn houses, and much more listed for rent in Oregon.

These would certainly be among the best places to stay in Oregon when visiting.

To save the most money on your road trip through Oregon, consider sticking to hostels and campgrounds. Hostels in Oregon are quirky and full of character not to mention the most affordable form of accommodation.

If you’re feeling lucky, you could also try your hand at finding a host with Couchsurfing! Lots of people use this though so competition is quite high in Oregon.

Best Places to Stay in Oregon on a Budget

Camping in oregon.

Camping is absolutely one of the best ways to sleep on a road trip through Oregon because

• It’s cheap and…

There’s nothing better than a night outdoors with a car full of goodies, a roaring fire, and a good pint of camp whiskey. Americans love it, Oregonians especially love it, and so should you!

There are campgrounds everywhere in Oregon and in all sorts of varieties. There are standard sites, primitive sites, RV parks, glamping, something called “treetop camping” and many, many more types that just get more and more ridiculous. You can even stay the night in a fire lookout , which has to be one of the coolest places to stay in Oregon.

You can use this search engine to find a campground in Oregon . Be sure to keep your eye an AirBnB as well – there are lots of interesting private camps listed.

Campgrounds in Oregon offer a range of amenities and at a range of prices. Most facilities will require a small fee to be paid, which goes toward keeping the grounds tidy and clean.

You can sometimes pay online but most of the time there will be a form at the actual site that you need complete on your own. Even though registrations from these are not always checked, please be respectful and pay the nominal fee for your stay.

If you intend on staying at a campground near of the more famous attractions in Oregon, like the Painted Hills, Smith Rock or Crater Lake, then you definitely consider reserving a space ahead, especially in the summer months. Campsites can fill up very quickly in Oregon.

If there appears to be no space leftover at your prospective campsite, there may still be walk-up sites available. Get to the grounds as early as possible to snag these spaces.

Camping in Oregon – Gear Checklist

Camping is one of the best ways to experience the USA, and Oregon has some of the finest camping in the whole country. You could sleep in your car or an RV while road tripping in Oregon, but sleeping outside under the stars is way more fun.

Having a good-quality camping tent  will keep you comfortable on those chilly nights and give you lots of flexibility when it comes to finding a place to sleep.

Here are some other essentials that we recommend if you plan on camping out…

Travel Security Belt

This is a regular looking belt with a concealed pocket on the inside – you can hide up to twenty notes inside and wear it through airport scanners without it setting them off.

Microfiber Towel

Hostel towels are scummy and take forever to dry. Microfibre towels dry quickly, are compact, lightweight, and can be used as a blanket or yoga mat if need be.

Petzl Actik Core Headlamp

A decent head torch could save your life. If you want to explore caves, unlit temples, or simply find your way to the bathroom during a blackout, a headtorch is a must.

‘Monopoly Deal’

Forget about Poker! Monopoly Deal is the single best travel card game that we have ever played. Works with 2-5 players and guarantees happy days.

Hanging Laundry Bag

Trust us, this is an absolute game changer. Super compact, a hanging mesh laundry bag stops your dirty clothes from stinking, you don’t know how much you need one of these… so just get it, thank us later.

For plenty more inspiration on what to pack, check out my full road trip packing list .

Drink water from ANYWHERE. The Grayl Geopress is the worlds leading filtered water bottle protecting you from all manner of waterborne nasties.

Single-use plastic bottles are a MASSIVE threat to marine life. Be a part of the solution and travel with a filter water bottle. Save money and the environment!

We’ve tested the Geopress  rigorously  from the icy heights of Pakistan to the tropical jungles of Bali, and can confirm: it’s the best water bottle you’ll ever buy!

Free Camping in Oregon

Those on a road trip in Oregon should totally take advantage of the many free campgrounds spread throughout the state. Note that electricity, bathrooms, and running water are not guaranteed at any of these. Also be aware that many free campgrounds in Oregon may require a 4×4 vehicle to reach.

Refer below for a list of some of our favorite free campgrounds in Oregon or this website for a complete archive of free campgrounds.

Books to Read during your Oregon Road Trip

These are some of my favorite travel reads and books set in Oregon. Read one or two and you may have some great road trips ideas for Oregon…

• One Flew Over the Cuckoo’s Nest – One of Ken Kesey’s most famous novels, thanks in part to the film of the same name. Paints a picture of mental health and conformity through the lens of a man who’s just too full of life.
• Sometimes a Great Notion – Ken Kesey is a literary demigod in Oregon and this is arguably his greatest novel. A tale of a hardheaded logging family that goes on strike, leading the town to drama and tragedy.
• The River Why – A quintessential American coming-of-age tale, both for the protagonist and the nation the book represents. Set in Portland and the Oregon Coastal Range.
• Night Dogs – Vietnam War vet deals with violence in the streets and in himself. An excellent if not authentic crime novel.
• The Lathe of Heaven – A man wakes up one day to discover that his dreams can affect reality itself. A novel exploring human creation and destruction. Set in Portland, which was the ultimate home of the author, sci-fi legend Ursula K Guin.
• Dies the Fire – All electronics are rendered useless by a magnetic storm, resulting in humanity’s return to the Dark Ages. Brutality, desperation, and sword fights in Portland follow.
• Lonely Planet: Washington, Oregon, and the Pacific Northwest – It’s sometimes worth traveling with a guidebook.

Renting a car is the most popular way of getting around Oregon. There are a myriad of car rental agencies here that offer varying deals and varying models.

To find the best rental car deal in the USA, use search engines that compare the prices from individual companies. We personally like using rentalcars.com as they’ve never failed to give us a great price.

You can also rent an RV or campervan and travel by way of vanlife , which means you don’t have to worry about packing camping gear. You will have to empty and refill the various wascampete and water tanks though, which will require a visit to the proper facilities. RVs also cost more to rent, use more gas, and demand higher prices at campgrounds.

Make sure you also purchase a RentalCover.com policy to cover your rental vehicle against any common damages such as tires, windscreens, theft, and more at a fraction of the price you would pay at the rental desk.

We suggest booking a campervan with Outdoorsy as they usually have a good selection and good prices. Better yet, Broke Backpackers also get a $40 discount with Outdoorsy! Just use the coupon code “BACKPACKER” when checking out.

The roads in Oregon are generally very good and a sedan or economy car should deliver you to most of Oregon’s top destinations. Only in the most remote portions of the state and the Cascades, will the roads be so bad that you need 4×4 or at least high clearance.

If you’re on a road trip in Oregon during the winter and want to go to the mountains, you will definitely need all-wheel or 4-wheel drive.

Tips for Saving Money on Car Rentals in the US

• We mentioned before that you can reach out to vehicle relocation services, like immova and Cruise America , as a way of saving heaps of cash on rentals. Pursue these as best you can as they can save you a lot of money. Don’t get your hopes up too much though, as availability is always limited.
• Car insurance isn’t always mandatory in the USA but is highly encouraged. This being said, you don’t necessarily have to buy car insurance from the company you’re renting from. Purchase a RentalCover.com policy to cover your vehicle against any common damages such as tires, windscreens, theft, and more at a fraction of the price you would pay at the rental desk.
• Many credit card companies offer free car insurance if you book the car with the proper card. Call your credit card company for more information regarding terms and conditions.

Best Time to Visit Oregon

The best time to visit Oregon really depends on what you want to do. With lots of activities year round, you could go on a road trip in Oregon and always have something to do. Drinking beer is, of course, something that happens 365 days of the year.

There are several different climates in Oregon. Generally speaking, everything west of the Cascade Mountains is maritime e.g. there’s a lot more rain and mild temperatures. East of the Cascades is much drier and prone to extreme temperature shifts, which is a characteristic of the high desert.

Precipitation occurs almost always in the winter months regardless of location.

• Summer is a great time to visit Oregon because the skies are almost always clear and rainfall is sporadic. There are lots of festivals during this time of the year and most Oregonians spend their free time outdoors. What little rain does fall in the summer is usually the result of occasional storms, which sometimes come in the form of thunderstorms. Thunderstorms often cause forest fires, which have become more common in recent years due to increasing summer temperatures and decreasing rainfall.
• Spring and autumn are lovely seasons to visit Oregon but are somewhat brief. Summer usually goes into September and winter often feels very long (November-March).
• Winters in Western Oregon are notoriously dreary as rain falls almost every day and the skies are almost always overcast. Being the tortured souls that they are, Oregonians love to be homebodies and stay warm with a beer at this time.

Luckily, the Cascades and parts of Eastern Oregon receive plenty of snowfall in the winter, giving winter athletes plenty of opportunities. In fact, Oregon has some of the best slopes on the West Coast.

Things go wrong on the road ALL THE TIME. Be prepared for what life throws at you.

Buy an AMK Travel Medical Kit before you head out on your next adventure – don’t be daft!

Food in Oregon

Oregon is often ranked as one of the top foodie states in the country by several major publications; more often than naught, it’s #1. Thanks to a thriving farm-to-table scene and a population with a real culinary passion, Oregon has, seriously, some of the best food that you’ll ever eat.

Nearly every part of Oregon offers some amazing local product. To the east is grade-A cattle; to the west are the sublime bounties of the sea; and in the middle is the Willamette Valley, a hugely prosperous agricultural area.

When on a road trip in Oregon, there are so many ways to satiate your appetite. You can visit one of the many authentic farmers’ markets, swing by a roadside diner, book a table at a eclectic restaurant or eat at a food cart.

For those on a budget road trip in Oregon, I highly recommend eating at the small hole-in-the-wall joints and food trucks to save to money.

Hands down, the best food is found at the many food carts , for which Oregon is famous for. The food here is affordable, inventive, sometimes revolutionary, and always delicious.

Food carts are often labors of love, which means the food is extraordinarily cared for. If given the choice, I will always choose a food cart over a restaurant.

Like the anonymous food carts, the mom-and-pop restaurants found in bumfuck nowhere are also among the best things in Oregon. Simple as they may be in offerings, the ambiance and loving meals they provide are one of a kind.

I can think of many places that are so good they warrant road trips themselves. The gigantic burgers of Helvetia Tavern or the soothing ice cream of K & R Drive In are certainly worthy, if not sweet memories for me.

Get your Buzz On

Whether it’s because of the demand for alcohol during those depressing winter months or because the region produces some of the finest hops, grapes, and other botanicals for making beverages, makes no difference; Oregon loves to produce and consume booze in all of its forms.

Oregon makes some of the best wine, beer, and spirits in the USA and that is a fact that locals will defend with a fiery passion. (Go Pinot Noir, not California Cab.)

Agricultural epicenters like Hood River, the Willamette Valley, McMinnville, and Medford consistently produce the best booze in the state. Amongst these regions are dozens if not hundreds of wineries, distilleries, and breweries that offer countless alcoholic varieties.

Throw in the fact that many of these sites are located in gorgeous, bucolic settings and you have some of the most fun places to stay in Oregon.

If you had to choose one place to sample local wares or go party for that matter, it’d definitely be Portland. You cannot throw a rock in this city and not hit a bar; they’re simply everywhere.

Nearly every type of bar as well: dives, speakeasies, country haunts, beer halls, urban wineries, clubs, and many more. Strip clubs are particularly well represented in Portland, so much so that the city actually has the highest concentration per capita in the country beating out both Orlando and Las Vegas.

No piece about getting buzzed in Oregon would be complete without talking about the marijuana, which is 100% legal in the state. Like alcohol consumption, you must simply be over a certain age (21) and only smoke it in certain places like on your property or away from businesses. You can buy weed a local dispensary , which only requires you to bring an ID and cash.

Being a Responsible Backpacker in Oregon

Remember to be a respectful camper while on your Oregon road trip. Depart from the grounds at a decent hour, follow leave no trace principles, and be very, very aware of fire bans. Forest fires are an enormous problem in Oregon and are often caused by reckless campers.

Oregonians are also very conscious of the environment and like to take care of it, as should you.

Reduce your plastic footprint: Perhaps the best thing you can do for our planet is to make sure you do NOT add to the plastic problem all over the world. Don’t buy one-use water bottles, the plastic ends up in a landfill or in the ocean.

I know it can be hard, but do your best to use the least amount of plastic water bottles that you can. Refill the ones that you do buy! Use a Grayl Geopress . Refill at your hostel/guest house! There are plenty of ways to reduce plastic!!!

Pack a  tough and cool travel water bottle . You’ll use it every single day whether you are traveling or not! Help save the planet, and pick up a water bottle here.

Check out our post on how to be a responsible backpacker.

Make Money Online Whilst Traveling in Oregon

Want to stay in the USA longer? Worried that you don’t have enough cash for a longer Oregon road trip? One idea is to make money while traveling!

Teaching English online is a great way to earn a consistent income—from anywhere in the world with a good internet connection. Depending on your qualifications (or your motivation to obtain qualifications like a TEFL certificate) you can teach English remotely from your laptop, save some cash for your next adventure, and make a positive impact on the world by improving another person’s language skills!

It’s a win-win! Check out this detailed article for everything you need to know to start  teaching English online .

In addition to giving you the qualifications to teach English online, TEFL courses open up a huge range of opportunities and you can find teaching work all over the world. To find out more about TEFL courses and how you can teach English around the world, read my in-depth report on teaching English abroad .

Broke Backpacker readers get a 50% discount on TEFL courses with MyTEFL (simply enter the code PACK50), to find out more, please read my in-depth report on teaching English abroad.

Whether you are keen to teach English online or looking to take your teaching game a step further by finding a job teaching English in a foreign country, getting your TEFL certificate is absolutely a step in the right direction.

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A couple of you lovely readers suggested we set up a tip jar for direct support as an alternative to booking through our links. So we created one!

You can now buy The Broke Backpacker a coffee . If you like and use our content to plan your trips, it’s a much appreciated way to show appreciation 🙂

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The Ultimate Oregon Road Trip: Itinerary Inspiration and Must-See Stops

last Updated: May 17, 2021 bend cannon beach crater lake mt hood oregon portland road trip

FYI: Affiliate links may be sprinkled throughout the awesome, free content you see below. I’ll receive a small commission when you purchase from my links (at no extra cost to you), which I’ll totally blow on adult things like boba tea and avocado toast. As always, thanks for the support.

Are you ready to be blown away by shimmering lakes, snowy mountain tops, and enough craft beer to last a lifetime? Get ready for an Oregon road trip, my Pacific-Northwest-craving friends. Sharing tons of details below to get you started planning your trip to the Oregon coast and beyond!

Just last year I had never visited Oregon before. Yeah, yeah, shame on me (I kiiinda recently moved to the west coast so you’ll cut me some slack, yea?) ;p I visited for the first time last year, and let’s just say I’m a tad obsessed. I had heard Portland was kinda cool, and after one look at Crater Lake I knew I had to make it there sooner than later. Alas, my first few trips to Oregon were planned, and I’ve now found myself in the state 3 times within a ~6 month period (something that just NEVER happens).

So without further ado, I’m sharing my ideal Oregon road trip, from the quirkiness that is Portland south to the dazzling still water of Crater Lake and west to the allure that is the stunning Oregon coast.

Oregon Road Trip Itinerary Overview

• Stop 1: Portland (2-3 days)
• Stop 2: Columbia River Gorge/Multnomah Falls (1 day)
• Stop 3: Mt. Hood (1 day)
• Stop 4:  Silver Falls State Park (1 day)
• Stop 5: Smith Rock State Park (½-1 day) 
• Stop 6:  Painted Hills (½ day)
• Stop 7: Bend (1-2 days)
• Stop 8: Crater Lake (1-2 days)
• Stop 9: Ashland (1 day)
• Stop 10: Coos Bay / Southern Oregon Coast (1 day)
• Stop 11: Newport, Tillamook, and Cannon Beach (1-2 days)
• END: Portland

Over the course of the road trip, expect to drive approximately 24 hours (round trip) and around 1000 miles. You’ll notice on the map below that I haven’t included the drive from Portland to Silver Falls State Park (that’ll add another 2 hours or so to the time listed on the map), as well as the 1.5 hour drive back to Portland from Cannon Beach (limits of technology). In order to complete this Oregon road trip in a timely manner (a week to 10 days or so), you’ll be driving almost every day, with some being longer driving days than others. Plan accordingly and bring snacks! The time in the car doesn’t have to be absolutely horrible. :p

→ Read next: Top Tips for Long Car Trips // Long Road Trip Essentials

When to Visit Oregon

Like the rest of the Pacific Northwest, Oregon experiences four seasons. To be completely transparent (and as noted above), I visited these different spots in the state on a few different occasions. I visited Portland in early June, Crater Lake in early September, and Bend in the snowy winter months. Oregon is spectacular year round, but if you’re on the hunt for some sunshine and minimal precipitation, I’d recommend planning your Oregon road trip between the months of April and September.

The best month for visiting the Oregon Coast is typically September, as the summer months are usually pretty foggy. It’ll be the wettest throughout the state between November and March, and the warmest between June and September. The roads around Crater Lake typically don’t fully open to cars until July, so keep this in mind if you’re visiting prior!

If you have the luxury of picking exactly when to take your Oregon road trip, choose September! The weather is glorious – little to no rain, clear coastlines, and warm weather. Just like my home state of California, Oregon typically experiences an Indian Summer, which lasts until early-mid October.

Getting to Oregon (and Portland in particular)

First things first, if you’re not a resident of Oregon, you’ll of course need to get yourself there! Since PDX is a major international airport, it’s wise to start your Oregon road trip in Portland, as you’ll be able to find decently priced tickets from throughout the US, highly dependent on the airport you’re departing from. For reference, from SFO (San Francisco), I commonly see round trip tickets to PDX (Portland) for under $200, and many times under $150.

New Yorkers can fly to Portland for roughly $300 if bought far enough in advance. I swear by Skyscanner and Google Flights whenever searching for tickets, and more often times than not, find the cheapest prices on one of them. The ability to track prices (and get email notifications when the price drops) is top notch and one of my favorite features. Take advantage of Skyscanner , you guys, they’re seriously the best.

quirky coffee shops everywhere you go in Portland – this one’s in a converted school bus!

If you’ll be following this complete Oregon road trip itinerary you’ll be doing a full loop from Portland, hence the need for round trip tickets from PDX. If you’re coming from Northern California and don’t mind doing a bit of extra driving, you can start this road trip from wherever you see fit (Crater Lake is roughly 7-8 hours from San Francisco, and the southern Oregon Coast – Coos Bay – is about 9 hours). Just remember that you’ll need to head back to your original destination. 🙂

Since this is in fact a road trip , you’ll need a vehicle to get you from place to place! Worth mentioning so you don’t forget to account for the cost of a rental car when following this Oregon road trip! And since you’ll be returning the car in the same place you picked it up, no need for pesky extra drop-off fees. I commonly use this booking site when searching for low-cost car rental options, and like Skyscanner , frequently find great deals on there!

I like to search  via this site in order to compare rental companies to see who has the best price.

How Long Should This Oregon Road Trip Take?

In all honesty, that’s a kinda hard question to answer, as the duration of the trip highly depends on your interests and how long you wanna stay in each place. I’d say a week if you’re picking and choosing a few stops to 2 and a half weeks if you wanna see and do mostly everything on this Oregon itinerary at a leisurely pace.

Now let’s get this Oregon road trip under way!

The Complete Oregon Road Trip Itinerary

Stop #1: start in portland (2-3 days).

Portland, Oregon is best known for its delectable donuts, snobby coffee culture, orgasmic food, and, of course, for being weird. It is in their slogan after all! Two to three days in the city will give you enough time to see all the highlights, as well as eat to your heart’s content. It’s the best place to start your Oregon road trip since renting a car will be easy peasy if you’re flying into PDX.

With two days in Portland, you can easily fit in these activities:

• Pittock Mansion: Looking for spectacular views of the entire city? You’ll find those here at Pittock Mansion. Note that while the view is free to admire, a ticket is required to tour the mansion grounds.

• International Rose Test Garden (located within Washington Park): What’s better than rows and rows of sweet-smelling roses? Hint: not much. The garden boasts over 10,000 of the pretty things, in every color combination imaginable (over 650 varieties)! Wander around for a half hour or so, and be sure to actually stop and smell the roses (yes, pun intended). Make sure you visit when the roses are in bloom (April through October, although June is the peak season). FYI – Entrance to the garden is free, but you’ll need to pay a few bucks for parking.

• Powell’s City of Books: Book lovers, rejoice! You can easily spend hours (and hours) exploring Powell’s flagship store – you’ll even need a map (which they happily supply). Be warned: this place is HUGE huge (like, multiple floors with rooms opening into rooms opening into rooms, etc etc). It actually takes up an entire city block and then some. If you can’t find what you’re looking for, you’re just not looking hard enough – they have EVERYTHING imaginable and then some (new, used, rare, and even out-of-print books). I was like a kid in a candy store…

• Keep Portland Weird Sign: Right across from Voodoo Donuts you’ll find this quick photo spot → don’t miss this iconic mural! The sign itself is just a wall in a parking lot, but just go, be weird, and take your picture. The actual address is 350 W Burnside St in case you can’t find it (it’s right behind Dante’s).

• Tilikum Crossing: Have more time and looking for a scenic leisurely walk over the river? Head to Tilikum Crossing, also known as the “bridge of the people”, a .35 mile pedestrian, bike, and light rail bridge with unparalleled views of the Willamette River. Smart, right? Why don’t more cities have this (bridges that ban cars that is)? You can easily do this walk back and forth in under an hour. I reckon it’d be even more dramatic and scenic at night with all the city lights shining down on the river! Be sure to look out for the submarine near OSMI!

→ Read Next: 3 Perfect Days in Portland

Where (and what) to eat in Portland (my favorites):

• Pok Pok: order the Vietnamese fish sauce wings
• Blue Star Donuts: just do it, more than once (calories don’t count on vacation)
• Coffee at Stumptown: grab some at the airport if you don’t have time
• Salt and Straw ice cream: try some of their wacky flavors, changing all the time!
• Abyssinian Kitchen: some of the tastiest Ethiopian food around
• Katchka (Russian): try the herring under a fur coat, Siberian dumplings, lamb with rice, and cauliflower schnitzel (all super tasty)
• Pine State Biscuits: I’m drooling just thinking about my breakfast
• Fried Egg, I’m in Love: the best egg sandwiches in Portland, in my opinion
• Tov Coffee: located in a converted school bus; get “the mint thing”, it’s orgasmic
• Voodoo Donut: a Portland must-stop, even if everyone says Blue Star is better

Sleep: Portland (I’ve been lucky enough to stay with friends/family when visiting the area, but I’ve heard fantastic things about Ace Hotel Portland , Jupiter Hotel , Kimpton Hotel Monaco , and Stay Pineapple at Hotel Rose . Browse all hotels in Portland here .

Stop #2: Multnomah Falls and the Columbia River Gorge (1 day)

Distance: 30 miles to Multnomah Falls | Driving time: 45 minutes + driving through the Gorge

It’s time to grab those wheels (hint: car rental) and make our way towards our first official stop on this Oregon road trip, Multnomah Falls!

Being the tallest waterfall in all of Oregon state, a stop at Multnomah Falls really should be on any Oregon road trip itinerary, no matter how long or short. Looking up at the 600+ foot tall roaring cascade of icy water is awe-inspiring to say the least! It’s actually the most visited natural recreation site in the Pacific Northwest (whoaaa Nelly), so be prepared to share the views with 34,534 of your closest Portland-loving friends if you come after 10am. Visit before 9am and you’ll have the place almost to yourselves, season dependent.

Once Multnomah Falls is outta the way (and as noted earlier, head here early due to the crowds that arrive by 9/10am), continue on your waterfall-finding journey – there’s dozens upon dozens (!!!) of them in the Columbia River Gorge. The Gorge is essentially a canyon of the Columbia River, stretching more than 80 miles and up to 4,000 feet deep, and is kinda a divide between Washington and Oregon. With stunning vistas and enough waterfalls to last a lifetime, you’ll want to carve out at least half a day to explore.

Note that trails close on occasion due to wildfires, so you’ll want to make sure access is available before you set off on any hike. I’ve heard Horsetail Falls, Latourell Falls (it’s a few minutes before Multnomah, but go afterwards to beat the rush at Multnomah), and Wahkeena Falls are spectacular – but all were closed during my June 2018 visit due to the horrific fire in 2017.   Check for possible trail closures here .

Note that it’s about 45 minutes from Multnomah Falls to the town of Hood River, which is a good place to base yourself for the night. If you’re exploring other waterfalls in the Gorge, you’ll be even closer to Hood River.

Sleep: Hood River (Check out the Hampton Inn & Suites Hood River and the Best Western Plus Hood River – both great options). Browse all hotels near Hood River here.

Stop #3: Hood River and Mt. Hood (1 day)

Psst – if you’re really pressed for time you can combine stop #2 and #3 into one long day. It’s definitely doable, it’ll just be a little rushed. Do note that if you plan on doing some hiking, you’ll probably wanna split up the days, but your call! I visited everything in one day, but wasn’t able to do all the hiking I wanted due to the trail closures as mentioned above.

Distance: 47 miles to Timberline Lodge | Driving time: 1hr

Next up, Hood River, but first, a short pit stop at Rowena Crest . Sure, it’s about 25 minutes outta the way, but most definitely worth it for that instashot (I’m sure you’ve seen it somewhere – haha)! So what is it about this place that makes it rather popular?! Yes, it’s technically just a bend in the road but the surrounding scenery makes it a worthwhile stop.

This iconic horseshoe curve is actually one of the most photographed roads in all of Oregon! It does get pretty windy up here, so if you’re planning on taking that insta-photo, please be extra extra careful! Note that you’ll need to hoist yourself up and over the railing if you want more than just shoes in your shot (I was too much of a chicken to do so).

On your way to Mt. Hood, you’ll most likely wanna stop in Hood River for some lunch. My suggestion – Solstice Wood Fire Cafe for, you guessed it, some wood-fired pizza. Stretch those legs and go for a walk along the Hood River Waterfront for some great views of the area as well!

Additional pit stop: Hood River Lavender Farm ! An absolute must-stop for anyone who’s even a little bit lavender obsessed. Not only can you wander around the whole place smelling the sweet smells, but for $5, you can pick your own lavender to tie up and bring home! The place was smaller than I had expected, but there’s tons and tons of lavender bushes so it doesn’t even matter. Be extra careful when picking, as there’s lots of bees!

Be sure to look inside the gift shop for lavender jams/jellies, soaps, etc. If you come on a clear day you can even see Mt. Hood in the distance! FYI: Lavender picking season is from April/May to November, with peak bloom being July-August.

Wanna brag to your friends about finding the best views of Mt. Hood? Head to Trillium Lake , where the mountain literally reflects in the water and creates the most peaceful setting. What’s better than a mountain reflection in a jazzy blue lake? Not much! On a clear day, you’ll find Mt. Hood perfectly reflected in the water. Worth the short photo stop for sure! You can also walk around the lake for additional views as well, but we wanted to make it back by dinner so skipped the almost-2-mile loop trail. I want to visit during sunrise or sunset next time!

End this long day at Timberline , a mountain lodge right at the base of Mt. Hood, where you can watch the skiers summer ski and grab a bite to eat (if you’re so inclined). You of course can spend the night here if you’re planning on actually using the mountain for skiing or snowboarding (be sure to make reservations in advance), but we were just observers for the day.

Sleep in Mt Hood : Timberline Lodge if you’re feelin’ fancy, or check out Best Western Mt. Hood Inn or Collins Lake Resort for budget options in the area.

Stop #4 ( optional ): Silver Falls State Park (1 day)

(adds an extra 2-3 hours of driving time)

Distance : 94 miles to Silver Falls State Park | Driving time : 2hr plus traffic

→ Note that it’s more than possible to visit Silver Falls State Park as a day trip from Portland, so if you wanna do that and tack on a day to your Portland stop, feel free! → That’s what I did! It’s actually only about 1 hour, 15 minutes south of Portland, so if you prefer staying in the city and switching hotels one less time, a day trip to Silver Falls from Portland may be your best bet!

If the waterfall at Multnomah wasn’t enough for you, or you’re just a waterfall fanatic like myself, make the 2-3 hour detour to Silver Falls State Park. (Psst – I actually found the waterfall at Silver Falls State Park even more spectacular than those on the Columbia River Gorge). There are numerous trails available, with the easiest of them leading to the most impressive waterfall in the park – South Falls. You can even go behind some of them! Definitely reminded me of the some of the waterfalls I saw in Iceland!

If you’re looking for a longer hike, trek the entire 9 miles and you’ll be rewarded with 10 waterfalls (yes, 10!). Where else can you see 10 waterfalls on one hike?! We hiked about 3 miles or so and saw two waterfalls.

People actually call it the “crown jewel” of the Oregon State Parks system – you’ll quickly understand why after your first visit! I mean, who doesn’t appreciate a leisurely walk the rainforest (Oregon’s only one actually!)

Sleep : Browse all hotels near Silver Falls State Park here.

Stop #5: Smith Rock State Park (½ – 1 day)

Drive: 3 hours to Smith Rock State Park from Silver Falls State Park -or- 2 hours from Timberline

Located roughly 30 minutes north of Bend (next up on this Oregon road trip itinerary) in central Oregon’s High Desert (riiiight off the highway I might add), this is a spot you’d be absolutely mistaken to miss, no matter the weather. With scenic views of deep river canyons and ample hiking opportunities, Smith Rock is any outdoor-lovers dream. If you’re up for a workout on tons of switchbacks, head up to Misery Ridge for dramatic views of the entire canyon and nearby rock formations. This spot is a mecca for rock climbers, and even if you don’t subject yourself to Misery Ridge (it is called Misery Ridge for a reason), you can still spot them from the canyon floor.

we visited in winter, hence the reason we’re bundling up (obv)

Psst: if you’re an alpaca fanatic like I am (guilty!), be sure to check out Crescent Moon Ranch located in Terrebonne (right near Smith Rock State Park). make sure to head into the visitor’s lounge to pick up some alpaca food to feed the little guys and check out all the goods made from their soft, luxurious fleece. Wool sweaters, wool socks, wool stuffed animals, and oh so much more – it’s all there.

Sleep: near Smith Rock ( Sleep Inn & Suites Redmond and Best Western Plus Rama Inn are viable options) or in the areas of Mitchell / Prineville near the Painted Hills (depends if you wanna do more driving today)

Stop #6 ( optional ): Painted Hills and surrounding areas (1 day)

This minor detour to Painted Hills will take you roughly an hour and 45 minutes outta the way, but hey, you might as well see a lot of the state on this Oregon road trip. And plus, it’s one of the Seven Wonders of Oregon, so you kinda gotta see it.

The Painted Hills are just that – full of hills of a whole myriad of different colored soils, including yellows, golds, blacks, and reds. Top Tip: these different colors are best viewed in the late afternoon (the claystones appear different dependent on light and moisture).

But don’t leave just yet – the Painted Hills are just one of three units that make up the John Day Fossil Beds. You’ll find mars-like landscapes at the Clarno Unit, and fossils of plants and animals at the Sheep Rock Unit (which make up 55 million years of evolution with a giant collection of 40,000 fossils). And no, I didn’t exaggerate those numbers. It’s the real deal over in these parts! All of these three units have short trails to dramatic viewpoints of colorful rock formations – you could easily spend all day here. Note that the three units are roughly 1 hour away from each other, so you’ll need to account for some extra driving should you want to visit two or all three.

→ Important: If you’re staying after dark to watch the sunset (highly recommended), be extra careful when driving to your accommodations at night. There’s lots of wildlife out and about near the roads (deer, elk, etc).

Note that today’s kinda a lot of driving if you decide to see Smith Rock and the Painted Hills in one day, so you may want to consider sleeping in Mitchell near the Painted Hills (30 min drive) and driving to Bend the next morning. If you wanna get a head start the drive to Bend, sleep in Prineville (roughly 1 hr, 15 minutes from the Painted Hills and on the way to Bend).

Sleep : Bend at LOGE Entrada Bend (where I stayed and brand spankin-new) or The Oxford Hotel (another top-notch option recommended by a couple we met on our Craft Beverage Tour).   Browse all hotels in Bend here . (or Mitchell / Prineville near the Painted Hills)

Stop #7: Bend (2-3 days)

Drive: 2 hours to Bend from the Painted Hills

Located between the snow-covered peaks of the Cascade Mountains and the high desert plateaus of Central Oregon, Bend really has it all, and then some. Because of its prime location for outdoor activities (think hiking, biking, river sports, etc), you’ll find a ton of sporty enthusiasts living the rugged lifestyle.

Bend is basically an adults playground. And the town is super cute, too, with a whole slew of mouthwatering restaurants and cafes to indulge in!

As noted above, we visited Bend in it’s snowy winter months , and have yet to experience the area in all it’s warm-weather summer-glory. We fully enjoyed our time in Bend covered in snow, and went snowshoeing, took a craft beverage tour, and ate everything in sight (for real).

However, since I have a feeling you’ll be planning this Oregon road trip for a warmer month, I’ve compiled some of the best things to do in Bend sans piles and piles of snow. I have a few friends and cousins who frequent the area quite often (they’re Bend-obsessed), so I got some recommendations from them for you to enjoy.

Since Bend is sooo well known for its craft beers, you can’t leave town without taking part in the fun for at least a little while. The city is actually known as Beer Town USA, and has more breweries per capita than any other city in Oregon. Craft beverage tours like the Bend Ale Trail or the Local Pour Tour with Wanderlust Tours are especially popular to sample local sips.

We loved the mixture of the Local Pour Tour, visiting a local cidery, kombucha tap room, a whisky distillery, and of course a brewery. There’s even a non-alcoholic beer brewed for pups! Crazy, right?! They do love their beer over in Bend! If you’re a beer fanatic as well, you may want to schedule your trip to Bend during one of it’s many annual beer celebrations, including Central Oregon Beer Week, Bend BrewFest, or Bend Oktoberfest (among many, many more).

Alternatively, simply wander around the Old Mill District and Downtown Bend, which have tons of places to eat, stroll, or shop.

Outdoor lovers will also find tons to do here. During the summer, book a kayaking or canoeing expedition on the Cascade Lakes or the Deschutes River with Wanderlust Tours, who we actually went snowshoeing with in the winter and LOVED!

You can also enjoy the outdoors on foot or by bike, and you’ll see tons of people out on the trails on warm, sunny days. The Pilot Butte Trail is a popular hiking trail in Bend that takes you to the top of an extinct volcano (yup, I said volcano alright), with thrilling views of the surrounding Cascade Mountains nearby. It’s a beautiful, scenic trail for beginners and seasoned hikers alike. For bikers, you can’t beat the Deschutes River Trail, which extends over 12 miles and borders the Deschutes River, winding through canyons and beautiful green forests along the way.

what you can expect Bend to look like in the winter (that snow, swoon)

And if you’re looking to amp up your photography skills, book yourself a private lesson with Toni from Bend Photo Tours. She was oh so patient with me and answered all my silly (and quite embarrassing) questions without batting an eye. Next time I’m there I’m hoping the weather conditions are sufficient for some night-sky photography!

→ Read Next: A Snowy Weekend Trip to Bend, Oregon

Sleep: Bend at LOGE Entrada Bend (where I stayed and brand spankin-new) or The Oxford Hotel (another top-notch option recommended by a couple we met on our Craft Beverage Tour).   Browse all hotels in Bend here .

Stop #8: Crater Lake National Park (2 days)

Drive: 2 hours, 30 minutes to Crater Lake National Park from Bend

Crater Lake National Park has got to be one of the most mesmerizing places I’ve been to date, and thankfully, it’s up next on this Oregon road trip. With its calm dazzling blue waters, scenic highways, and super starry night skies, you can be sure you’ll never forget your visit to Crater Lake. And that’s a promise!

Some quick facts:

• Crater Lake is currently the 10th-deepest lake in the world, with a maximum depth of almost 600 meters (1,949 feet). It’s also the deepest lake in the USA!
• The magnificent intense blue color of Crater Lake is primarily due to it’s great, great depth, and remarkable clarity. The waters stay so clear since the lake has no other bodies of water flowing into it, meaning little-to-no pollution!  

We spent most of our time hiking, but there’s lot more to do at the National Park if hiking isn’t your jam. Revel in the views from Rim Drive’s multitude of lookout points, get some fancy drinks and/or a dessert at Crater Lake Lodge, take a boat cruise to Wizard Island, and even go for a swim (if you dare to step foot in the chilly waters)!

Although the park is open every single day of the year, many of the park’s roads, trails, and facilities are closed seasonally due to snow, which usually do not reopen until summer (June/July). If you want to ensure you’ll be able to drive around the perimeter of the lake (Rim Drive), schedule your trip for late July, August, or September. These also happen to be the most popular times to visit Crater Lake, but don’t fret – the park is rather large so you’ll still be able to find your own spots of peace and solitude.  

Sleep : Melita’s Crater Lake Lodge nearby Crater Lake (or you can head right to Ashland if you prefer). Browse all hotels near Crater Lake National Park here.

Stop #9: Ashland (1 day) – OPTIONAL

Drive: 2 hours to Ashland from Crater Lake National Park

Get one last look at Crater Lake, then hit the road; it’s time to make our way to Ashland, one of southern Oregon’s hot spots and loved by all.

Ashland is a classic Pacific Northwest hippie town with a love for nature, beer, and admittedly, all things weird. Here, you can find a very alternative vibe, with tons of green, vegan health shops, locally-brewed beers, and tons of places where you can get in touch with the quirky and downright strange personality of the place.

It’s not everywhere that you can watch Shakespeare, drink Sriracha flavored beer, and go to a paranormal activity hotspot in just one day. But in Ashland, you can do all this and more! Told you it was weird.

Speaking of Shakespeare, The Oregon Shakespeare Festival (OSF) is a must-see here, with regular shows at the Green Show, a performance venue and courtyard that’s frequented by visitors and locals alike. But if you’re not a fan of Shakespeare himself (say what?!), you can see other productions the group puts on, like Hairspray and Alice in Wonderland. The OSF shows usually happen during the summer, and if you choose to go to a classic Shakespeare show, don’t miss the ones at the Allen Elizabethan Theatre.

Aside from Shakespeare, there are tons of other weird and wacky things to do in Ashland. Beer lovers can find the strangest and most unique beers at the Caldera Brewing Tap House, a local favorite that made waves with its Sriracha Stout beer. You can also visit the Oregon Vortex, which is a weirdly spiritual spot known for paranormal activity and other strange happenings located about 30 minutes from town. And of course, don’t forget to enjoy the beautiful nature in the area, especially in the fall, when the leaves turn all kinds of beautiful colors.

Technically , if you wanna save a bit of driving and don’t have all the time in the world, you may choose to cut Ashland out of your Oregon itinerary. Your call, but I think it’s worth at least a day or so.

Sleep: Bard’s Inn Ashland . Browse all hotels in Ashland here.

Stop #10: Coos Bay // Southern Oregon Coast (1-2 days)

Drive: 3 hours, 15 minutes from Ashland to Coos Bay

It’s finally time to get this Oregon coast road trip itinerary underway! The drive from Ashland and Crater Lake will essentially take the same amount of time, so there’s no absolute NEED to visit Ashland if you’re pressed on time.  If you’re coming from either one, you have two options – the long way (~5 hour drive with more exploration of the southern Oregon coast), or the shorter way (3 and a half hours cutting straight to Coos Bay from Ashland/Crater Lake). I suggest opting for the short route as in my opinion, you won’t be missing out on too much by skipping the southern coast below (as Coos Bay is one of most scenic areas on the Oregon Coast)– but obviously, your choice!

Coos Bay is home to the Cape Arago Beach Loop, which is where I’d spend the rest of the day.

On this driving/exploring/sightseeing loop, you’ll venture into three Oregon State Parks, watch a ton of seals and sea lions play, as well as stop at numerous breathtaking vantage points. The drive is not super long, but you’ll definitely want the better portion of the day to stop and soak it all in!

A few must-see stops: 1) Bastendorff Beach (say goodbye to crowds and hello to oh so much natural beauty), 2) Sunset Bay State Park (those towering sea cliffs sure are something, especially with the beautiful sandy beaches and amazing tide pool explorations), 3) Cape Arago Lighthouse Viewpoint (you unfortunately can’t view the inside but you can get fantastic views from here), 4) Shore Acres State Park and Botanical Gardens (tons and tons of blooms), 5) Simpson Beach (look out for the migrating whales and hundreds of seals and sea lions), 6) Shell Island (breeding and rest areas for seabirds and Marine mammals), and finally 7) Cape Arago State Park.

Sleep in Coos Bay : Browse all hotels near Coos Bay here.

Stop #11: Newport, Tillamook, and Cannon Beach (2 days)

Next up on this Oregon coast road trip → making the way back up north to Cannon Beach!

Prepare yourself as today’s primarily a driving day, but don’t worry, there’s tons of scenic stops along the way. Think scenic seaside towns, sand dunes, spectacular lighthouses, and cheese! Yes, cheese! Because who isn’t fascinated by cheese?

Sure, California’s Highway One surely steals the show when it comes to coastal road trips, but Oregon’s coast is one for the bucket list as well! With quiet seaside coves, bustling beach towns, and secluded hideaways, you won’t want to miss the beauty that is Oregon.

A few recommended stops between Coos Bay and Cannon Beach, where we’ll be ending the drive today. If you’re not pressed on time you can easily spread these activities/stops out over two days.

• Oregon Dunes National Recreation Area: Wind-sculpted sand dunes for days (literally, miles and miles and miles). This NRA is actually one of the largest expanses of temperate coastal sand dunes in the world, so yea, I wasn’t kidding when I said Oregon’s coastline is on par with California’s .  You can even take a buggy or ATV tour of the dunes!
• Haceta Head Lighthouse : The first of numerous lighthouses on our list, and this one just happens to be the brightest light on the Oregon coast and most photographed in the whole state. To say it’s simply stunning is a huge understatement.
• Cape Perpetua: Don’t miss the Spouting Horn, an exploding salt water geyser, and Thor’s Well, a gaping pit with violent waves crashing in every direction that ultimately fall into a hole, just as weird and wonderful as it sounds.
• Nye Beach: The perfect stop for a late lunch, depending on how much exploring/sand-duning you did earlier. This is also a great place to spend the night if you’ll be splitting the drive from Coos Bay to Cannon Beach into two days.
• Yaquina Head Light: Being the tallest lighthouse on the Oregon Coast, you can’t miss this towering beauty
• Devils Punchbowl State Reserve: This is a popular whale watching site and displays an intriguing geology. Also, as the name suggests, there’s a hollow rock formation shaped like a huge punch bowl. Better yet, go at sunset if you want to see something spectacular.
• Tillamook Cheese Factory: Who could resist some fine, fine creamy cheese samples? Not I, that’s for sure! If you’re not familiar with the brand, Tillamook is a leading cheese provider in the area, who aims to connect farmers with everyday food lovers (hi!) with cheese and ice cream. Don’t miss the tour.
• Cannon Beach: Phew, made it (finally)! HAYSTACK ROCK, enough said.

Finally, the last official stop on this Oregon coast road trip, the one and only Cannon Beach. Here at Cannon Beach, you’ll find the famous and ever-so-popular Haystack Rock (it’s a sight to be seen).

No matter where you stand, you’ll see it (I promise), as it towers 235 feet over the beach. If you can, plan your visit during low tide so you’re able to walk right up to Haystack Rock to search for sea creatures (crabs, sea anemone, mussels, and snails). Check here to see when the tide is at its lowest. Check out Pelican Brewing Company should you get hungry (the fish tacos were absolutely bomb).

Sleep: Hallmark Resort and Spa Cannon Beach or Surfsand Resort if you’re feeling fancy, or Hidden Villa Cottages for a less expensive room. Note that many of the hotels are quite expensive in Cannon Beach, so expect to pay at least $250 a night or so.

Thankfully, you’ve only got about an hour and a half drive west back to the city of Portland to complete this full Oregon road trip. Choose to drive back after your first night in Cannon Beach, or the morning after your second.

End: Portland → Phew, you made it back! Grab some Stumptown Coffee on your way home!

Are you visiting the state soon? What are you most excited about on this Oregon road trip itinerary!?

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April 5, 2024 at 8:41 am

Sharp photos! Bend is definitely vibrant in the summer. You should make the trip. Be sure to check out Galveston and the oldmill district =)

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The Perfect 4 Day Oregon Road Trip Itinerary

Oregon may be one of the most underrated states in the US! While it has gained popularity in recent years it is still overshadowed by Washington to the North and California to the South. Oregon is a land of raging waterfalls, towering mountains, and stunning coastline, that should be on everyone’s travel list! The perfect way to see the most of Oregon is a road trip throughout the state! While a 7-day road trip may be ideal, there is still so much you can see with only 4 days in Oregon. Starting in Portland , travel to Multnomah Falls, Mount Hood, Bend, Crater Lake , and up the Oregon Coast on this perfect 4-day Oregon road trip itinerary.

Map of 4-Day Oregon Road Trip

The Oregon road trip map above begins in Portland Oregon and travels to the major scenic sites in Oregon. Travel from Portland to Bend on your first day, stopping in the Columbia River Gorge and Mount Hood . On the second day, explore Bend and travel to Crater Lake National Park . Day three check out another stunning Oregon waterfall before venturing over to the Oregon Coast. Day 4 see the best Oregon Coast stops including Thor’s Well, Cannon Beach, and many more before heading back to Portland.

This 4-day trip takes around 830 miles and 18 hours of driving with an average of 4 hours of driving each day. This is interspersed with many scenic spots, and there are opportunities to cut out spots if you prefer less driving. Rent a car from Portland to give yourself as much flexibility as possible.

4 Day Oregon Road Trip Packing List

Disclosure: Some of the links below are affiliate links. This means that, at zero cost to you, I will earn an affiliate commission if you click through the link and finalize a purchase.

• Raincoat-  You don’t want to visit Oregon without a rain jacket. This also works as a windbreaker-   My Favorite Rain Jacket
• Fleece-  A fleece or mid-layer is great to have when hiking so you can easily take it off to cool down-  Soft REI Fleece
• Day Pack – If you plan on doing a decent amount of hiking a day pack is always great to bring-  Recommended Osprey Day Pack
• Beanie or Hat-  You never know when the wind may pick up, so it is a good idea to always hike with a hat-  Warm Beanie
• Waterproof Boots – Trails near the coast and waterfalls are often muddy. Make sure to bring waterproof boots-  My Favorite Hiking Boots
• Moisture-Wicking Pants – While they do not need to be waterproof, you will likely want either moisture-wicking or quick-drying pants if the forecast calls for rain-  Comfortable Women’s Hiking Pants
• Sandals – If visiting in the summer and you plan on spending a long time at the beach, bring a pair of sandals to change into-  Teva Sandals
• Water Bottle – If hiking, bring a water bottle to hydrate-  Water Bottle
• Sunscreen – Make sure to wear sunscreen outdoors-  SPF 50 Sunscreen
• Camera-  Bring a camera to capture your memories!-   Beginner Travel Camera

4 Day Oregon Road Trip Itinerary

Day 1: Portland to Mount Hood and Bend

• Portland to Bend Distance: 211 miles
• Portland to Bend Driving Time: 4 hours 38 minutes

You will likely start your Oregon road trip in Portland if you are flying in. This makes a great starting point, as it gives you easy access to the Columbia River Gorge and the Historic Columbia River Scenic Highway. Take the scenic route from Portland to Bend , by driving through the Gorge, stopping at a few waterfalls and overlooks. This adds a bit over an hour of driving than if you were to drive straight to Bend, but it is well worth it to see some of the best waterfalls in Oregon.

Upon reaching Hood River , continue South around Mount Hood, and then on US-26 and US-97 the remaining way to Bend. A few must-see stops are Trillium Lake or the Timberline Lodge for a view of Mount Hood, and Smith Rock State Park near Bend!

Columbia River Gorge

The Columbia River Gorge Scenic Area ranges from just East of Portland out to Hood River. There are many viewpoints and stops on the way, so make sure to choose a few on your trip down the Gorge!

Vista House is one of the best spots to view the Columbia River Gorge. It is over 100 years old and is open from 9 AM to 5 PM. This is also a great spot to view sunrise near Portland. Another great viewpoint is Beacon Rock Trail which is only 1.5 miles and one of the best hikes in the Columbia River Gorge !

Best Waterfalls in the Columbia River Gorge

A trip to the Columbia River Gorge is not complete without visiting some waterfalls! The Columbia River Gorge has some of the best waterfalls in all of Oregon, accessible by trails ranging from easy to difficult.

• Multnomah Falls- Multnomah Falls is the most popular and tallest waterfall in Oregon. It can be accessed by a short walk from the parking lot, or you can do a more difficult hike up to the top of the falls.
• Wahclella Falls- 1.9 miles, 223 feet, Easy – Wahclella Falls is an easy 2-mile hike to one of the best waterfalls in the Columbia River Gorge
• Latourell Falls – 3 miles, 728 feet, Moderate – It is only a quarter of a mile to Latourell Falls, or you can do a loop hike up to Upper Latourell Falls as well.
• Horsetail Falls- Horsetail Falls is a short walk from the parking lot and accessible to everyone.
• Bridal Veil Falls –  0.5 miles, 78 feet, Easy – Many wouldn’t consider this a true hike, but nevertheless, it is well worth your time. Bridal Veil Falls is only a quarter of a mile from the parking lot, and the overlook gives a spectacular view of the two-tiered, over 100-foot waterfall.

Read More: Best Waterfall Hikes Near Portland

After driving through the Gorge you will reach the picturesque town of Hood River. In the Spring this is a great time to see wildflowers , or you can make a stop to pick fruit or try wine at one of the many orchards and vineyards on the Fruit Loop in Hood River! The  Gorge White House  is a popular family-owned spot that serves fresh fruit, wine, and cider out of a historic 1906 house.

Read More: Wildflower Hikes in Oregon & Washington

Next, you will drive up by Mount Hood before continuing on to Bend. While you may not have time for a long hike, consider a short stop at a viewpoint to see the majestic Mount Hood!

Mount Hood Viewpoints:

• Trillium Lake
• White River West Sno-Park
• Timberline Trail

Smith Rock State Park

Your last stop of the day will be at Smith Rock State Park . Smith Rock is located about 30 minutes from Bend, Oregon, and is the perfect spot to view the sunset! You can walk a short distance to see the iconic view of the Crooked River Trail snaking by the steep rock walls. If you have more time, hike along the river and admire the beautiful State Park.

Where to Stay Near Bend

Hotels near bend.

• Campfire Hotel – This cute hotel is perfectly nature themed for your Oregon road trip
• McMenamins Old St. Francis School – McMenamins is a staple throughout Oregon and offers unique accommodations and restaurants. This converted school even has hot soaking pools you can enjoy.
• Bunk & Brew Historic Lucas House Hostel – If you’re more on a budget there is a hostel with both private and shared rooms in a historic brick house.

Rentals Near Bend

• Riverfront Retreat –  A larger home on the river is perfect for a group trip or family get together
• Cabin Near Bend – This adorable cabin was perfect to be near Bend but still in nature
• Ranch Guesthouse Near Bend – If you’re looking for something a little more remote. This cozy guesthouse is about 15 minutes from Bend.

Day 2: Bend and Crater Lake

• Bend to Crater Lake Distance: 161 miles
• Bend to Crater Lake Driving Time: 3 hours 18 minutes

Spend the morning in Bend and the evening in Crater Lake for the perfect day 2 of your Oregon road trip. There are not many stops in between, so spend some time enjoying Bend’s famous site s before heading off.

The route to Crater Lake is very easy to follow- just take US-97 south to Chiloquin before venturing up on OR-422 and OR-62 to Crater Lake National Park.

Bend is a unique outdoorsy town at the foot of the Cascade Mountains. Spend the morning exploring Bend and the surrounding area before continuing on. Below is a summary of some of the best things you can do in Bend.

Also don’t forget to pick up breakfast at one of the many coffee roasteries based in Bend. Bend is well known for its coffee so you really can’t go wrong! Bend also had a thriving brewery scene, so after a morning outdoor activity cool off at one of the local breweries such as Deschutes Brewery or Crux Fermentation Project .

Best Things to Do Near Bend

Bend has so much to do it is hard to choose! Below are just a few of the activities you could pick from to squeeze in for a half day in Bend.

• See the city and mountains from Pilot Butte
• Go on a guided climb in Smith Rock State Park
• Rent a paddleboard and float down the Deschutes River
• Take an ATV Tour   through the desert
• Chase waterfalls like Tumalo Falls
• Stop by the Last Blockbuster
• Visit the High Desert Museum  
• Go hiking at Newberry National Monument

Read More: Weekend Itinerary in Bend, Oregon

Crater Lake National Park

After having your fill in Bend, drive the 90 miles down to Crater Lake National Park . Crater Lake is a beautiful National Park and easy to see in half a day! I would recommend picking a sunset hike such as The Watchman Peak Trail to admire the stunning lake. Depending on the time of year you can also drive or bike around the rim and stop at the viewpoints!

Where to Stay Near Crater Lake

Hotels near crater lake.

• Crater Lake Lodge – This is the only hotel inside the National Park! Like most National Park’s lodges, this is not the cheapest option, but you can’t beat the location.
• Crater Lake Resort – This is about 30 minutes outside of the National Park and has both tent sites and cabins for rent.
• Sleep Inn in Chiloquin – A standard hotel about 45 minutes outside the park.

Rentals Near Crater Lake

• Cabin on Umpqua River – This Cabin is a bit further North of Crater Lake but is right on the way to the locations on Day 3 of your Oregon road trip.
• Tiny Home Near Crater Lake – This ranch tiny home is just 19 miles from Crater Lake National Park.
• Cabin on the River – This cabin on a river is about 30 minutes from Crater Lake.

Day 3: Crater Lake to the Oregon Coast

• Crater Lake to the Oregon Coast Distance: 201 miles
• Crater Lake to the Oregon Coast Driving Time: 4 hours 16 minutes

Day 3 of your Oregon road trip itinerary will take you from the mountains to the coast! First, head up from Crater Lake with a quick stop at Toketee Falls ! Then continue taking OR-138 all the way out to the coast. From there you will turn onto the scenic 101.

Most of the rest of the trip will be spent driving up the 101 along the coast. Don’t be afraid to stop at the many pull-offs and take in the views! Some key stops on this day include the Oregon Dunes, Sea Lion Caves, and Heceta Head Lighthouse.

Toketee Falls

Toketee Falls   is a quick stop on the way toward the Oregon Coast in  Umpqua National Forest . It is only half a mile each way to an overlook of the 113-foot-tall waterfall. This is one of the most famous waterfalls in Oregon, iconic for the basalt columns that surround it.

The Oregon Dunes

Below are a  few great hikes near the Oregon Dunes . When searching for hikes on the Oregon Dunes, be sure to check if the trail is hiking only. Many trails in this area are also ATV trails.

• John Dellenback Trail – 5.5 miles, 308 feet, Moderate – If you hike the entire trail it will lead you to the beach. You can also hike just part of the trail to experience walking on the dunes! Please note that dogs are not allowed from March through September.
• Threemile Lake Trail – 6.1 miles, 997 miles, Moderate – This trail leads to a lake near the shore and leads you through both sand dunes and lush forests.
• Hall Lake Loop – 1.6 miles, 154 feet, Easy – This is a shorter trail in the sand around Hall Lake, and features a waterfall during certain times of the year.

If you have more time, you can also rent an ATV from somewhere like Spinreel Dune Buggy and ATV Rental and explore the dunes with 4 wheels.

Heceta Head Lighthouse & Sea Lion Caves

Stop by  Heceta Head Lighthouse and the  Sea Lion Caves . These two spots are right next to each other, so it is easy to see both.

Sea Lion Caves

The Sea Lion Caves cost $14 per person to descend into the caves and see the wildlife up close. The sea lions are not always present, so you can call ahead to confirm, or stop by and ask before purchasing a ticket.

Right past the caves is the Lighthouse and Sea Lion Beach Vantage Point . This is a free pull-off that gives a good photo opportunity of Heceta Head Lighthouse and Cape Cove.

Heceta Head Lighthouse

For a small fee, you can park in the day-use area and walk closer to the lighthouse. It is only 0.5 miles to the lighthouse. For a longer hike, continue on the  Heceta Head Lighthouse Trail to Hobbit Beach , a   3.6-mile round-trip walk.

There are not many places to stay here, so you will likely want to continue on to Yachats, Oregon for the night.

Where to Stay Near Yachats

Hotels near yachats.

• Heceta Lighthouse Bed & Breakfast – You can stay in the Heceta Head lightkeepers house turned bed & breakfast!
• Adobe Resort – This is a 3-star hotel with a beautiful sea view in Yachats!
• Overleaf Lodge & Spa – For a slightly nicer stay, relax at the Overleaf Lodge and Spa in Yachats

Rentals Near Yachats

• Cottage with Hot Tub – This little cottage is close to the Ocean in Yachats.
• Earthworks Art House – This stay is adjacent to the Earthworks Gallery and a rhododendron preserve
• Cozy Beach Cottage – This little cottage is dog friendly and within an easy walk to the beach

Day 4: Road Trip up the Oregon Coast

• Oregon Coast back to Portland Distance: 262 miles
• Oregon Coast back to Portland Driving Time: 5 hours 50 minutes

This is the longest driving day on your 4-Day Oregon coast road trip itinerary but it is interspersed with lots of quick stops! You can also cut down on the driving time by staying the night in Astoria or Cannon Beach or cutting out Astoria entirely and heading straight to Portland from Cannon Beach.

The majority of the driving is done along the 101 which has scenic ocean views almost the whole way! Some must-see stops are listed below including Thor’s Well, Yaquina Lighthouse, Cannon Beach , and Astoria . If you want to see even more here is a list of the best things to see on the Oregon Coast.

Thor’s Well

Thor’s Well is a quick stop, but a must-see on the Oregon Coast. This unique rock formation forms a hole in the coastline. At low tide, it is fun to watch the waves crash against the rock and soar up through the hole before being sucked back out to sea. However, it is high tide where Thor’s Well really shines.

High tide is the  best time to see and photograph Thor’s Well . The ocean covers the hole, meaning the water drains right through, looking like a hole in the ocean! To time your visit right, check a tide chart and visit at high or close to high tide.

There is a short dirt path to get closer to a lookout of the well. This should be accessible for most people. The tide will depend on how close you can get to the well. Always be careful of high waves that can reach further than you may expect. If you can’t hike closer to the well, it is also visible right off the road.

Yaquina Lighthouse

Lighthouses are always a must-see on the coast The  Yaquina Lighthouse  in the  Yaquina Bay State Recreation Site  is one of the best because it will let you walk inside! You can check the lighthouse website for up-to-date information on if the lighthouse is open. 

From the same parking area as the lighthouse, you can walk down to  Cobble Beach . Cobble Beach is a small beach with interesting black spherical rocks and many tide pools.

Oswald West State Park

Oswald West is one of the best State Parks in Oregon. There are hikes ranging from a short walk to several miles, and it has spectacular views of the coast!

Best Hikes in Oswald West State Park

Pick a short or longer hike in Oswald West State Park depending on the time you have. If nothing else, I would highly recommend taking the short walk to Short Sand Beach .

• Short Sand Beach – 0.6 miles, Easy – Short Sand Beach is more of a quick walk than a hike and is the best option if you are short on time. Explore this beach cove before heading up the coastline!
• Cape Falcon Trail –  4.6 miles, 623 feet elevation, Moderate – This trail starts from the same trail that leads to Short Sand Beach or an alternative trailhead. The end goal of this hike leads to a viewpoint of Cape Falcon.
• Neahkahnie Mountain –  2.8 miles, 866 feet, Difficult – This is the more maintained of two trails up Neahkahnie Mountain. This trail has amazing views of the coastline from the mountaintop

Cannon Beach

Cannon Beach  is a must-see when visiting Oregon. It is one of the most popular beaches due to its proximity to Portland, and the impressive 235-foot-tall  Haystack Rock  that dominates the view. This beach is huge, so there is plenty of room to wander or have a picnic!

Depending on the time of day you visit, Cannon Beach is a great place to stop for lunch! The seafood here cannot be beaten, and like much of Oregon, there are plenty of breweries to choose from.  Pelican Brewing  and  Public Coast Brewing  are two popular breweries in Cannon Beach.    Ecola Seafood Restaurant and Market   has a laid-back atmosphere and classic seafood options including Oregon’s famous Dungeness Crab. Dine in or take some to go, and enjoy your food with an ocean view!

Astoria is the most Northern Oregon coastal town, but well worth the visit! You may recognize many spots there as filming locations for popular movies like The Goonies.

This is the last spot on your itinerary, so fill in any remaining time you have exploring the town and nearby coast before making your way back to Portland!

Things To Do in Astoria

Like many towns on this list, Astoria has more to do than can be fit in the day, but you can see one or two of the highlights, depending on your preferences while in this coastal town! Below are just some of the best things to do nearby.

• Cathedral Tree Trail   is a short hike in downtown Astoria
• Ride the Historic Trolley along the riverfront
• See the Astoria-Megler Bridge
• Photograph the Peter Iredale Shipwreck
• Go hiking in Cape Disappointment State Park
• Visit the   Columbia River Maritime Museum

Read More: Things to Do in Astoria

Alternative Itinerary- 4 Day Oregon Coast Road Trip

If you would rather explore one area of Oregon more in-depth in your 4 days, I would recommend instead doing a  road trip of the Oregon coast . Start at  Astoria  and make your way down to  Brookings, Oregon.  You will be able to see many of the coastal places listed above as well as  Samuel H Boardman State Park, Devil’s Punchbowl, Ecola State Park, Cape Kiwanda , and many other stops.

If you have extra time you can continue on down to spend a day in the Redwoods and fly out of San Francisco.

• Day 1: Astoria and Cannon Beach
• Day 2: Cannon Beach to Lincoln City
• Day 3: Lincoln City to Florence
• Day 4: Florence to Brookings

Tips for Planning an Oregon Road Trip

• Check the weather for each area.  Oregon has a diverse landscape and the weather on the coast is likely very different from the Oregon desert! The weather will also be colder at higher elevations and many mountains do not clear of snow until late July or early August.
• Know tire chain requirements. In the Fall-Spring many mountain passes and the Columbia River Gorge requires tire chains. Check if they are required during your visit. You can also check mountain pass road conditions on the Oregon webcams.
• Buy an Oregon State Park pass. This itinerary includes a lot of state parks! You will likely save money and time by buying a 12-month day-use parking permit for $30 instead of paying the day fee in each park.
• Download your maps  ahead of time or print them off. The mountains and coast of Oregon often don’t get service.
• Make your reservations ahead of time – This is especially true if you want to camp in Summer. Campgrounds get very competitive in the Pacific Northwest
• Leave No Trace!   This is essential when hiking in any wilderness area. Don’t pick wildflowers (it’s illegal in Oregon!), don’t feed or pet wild animals, and take all trash with you. Stay on the trail when hiking, wandering off-trail destroys the environment and ruins the experience for others.

How Many Days for an Oregon Road Trip?

You may be wondering- how many days should I plan for an Oregon road trip?

I would recommend  7-10 days  to see as much as possible.  4 days  are enough to  hit the highlights , but you will likely walk away feeling as though there was still so much more to see. However, if 4 days are all you have, it is definitely worth it to make the trip and experience Oregon!

When to Road Trip Oregon?

Late Spring through Early Fall is the best time to visit Oregon . Summer will give you the most flexibility in things to do with warm weather all over the state. Keep in mind places like Crater Lake do not entirely lose their snow until into July. My personal recommendation would be to visit in mid to late September when the snow has likely not yet begun, but peak summer crowds have left. The itinerary above assumes that Crater Lake’s road is open to go out the North side.

As you can see above, the weather varies across Oregon. The coast remains mild throughout the year, rarely getting snow. Meanwhile, the mountains near Bend get coated every winter. If you are taking a Winter trip to Oregon, you’re itinerary and activities may need to look a little different to take advantage of the skiing and snowshoeing opportunities.

You May Also Like

• Scenic Day Trips from Portland
• Guide to Silver Falls State Park
• Mount Rainier in One Day

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The Best Oregon Road Trip: complete loop itinerary

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Summary: Best Oregon road trip, complete road trip itinerary, sunrise and sunset locations. *I use affiliate links and may receive a small commission on purchases. Thanks for your support!

Oregon was my first taste of the Pacific Northwest, and I’ve been smitten ever since. Most of these places I’ve learned about over the years or from passing through. I wish I would have done all of these in one epic Oregon road trip, so here ya go!

I recommend this road trip in the Summer time or the Fall, but it is possible to do during the Winter and Spring. Just be sure to check road closures and park closures when snow is a possibility!

The Route to the Best Oregon Road Trip!

I recommend Portland, Oregon as your starting and stopping point. This also makes it very convenient to fly into the Portland airport and start your adventure! I will link more information about where to stay in detailed blog posts about each spot.

Need to condense your trip? A lot of these spots are close enough where you can cover multiple locations in one day. As a photographer, I typically go to a new spot for sunrise and sunset!

Let’s Hit the Road!

1. multnomah falls.

Oregon has 238 waterfalls, and this is the tallest at 620 feet. Pretty mind blowing. View the Forest Service website HERE for latest updates. This spot does require reservations during the busy season! Check out more information on that and 15 other waterfalls on my Oregon Waterfall Guide!

2. Rowena Crest

This drive-up spot is pretty breathtaking. To the left of this horse-shoe road view is a view of the Columbia River Gorge. We went just before sunset as we were running from the rain!

3. Painted Hills

The drive in to the Painted Hills is, in my opinion, more beautiful than this little walkway. The striations of colors in the hills is stunning around golden hour and I imagine the same at sunrise!

This photo was taken at the Painted Cove Trail , maybe 30 seconds away from the parking lot. The entire trail is only .3 miles. See more details on AllTrails.

4. Smith Rock

Smith Rock State Park makes me believe dinosaurs once existed. This place feels very random, jutting out of the land with nothing else like it around. This is a climber and hikers haven! Check out my full blog post on what hikes to do and nearby camping: SMITH ROCK: A COMPLETE GUIDE TO VIEWING THIS OREGON WONDER

5. Tamolitch Falls Blue Pool

Tamolitch Falls, or more famously known as Blue Pool, is a short hike through a douglas fir forest and old lava flows. The end reveals an incredibly blue basin of frigid water. Read all about how it was formed, nearby camping and cabins, and photo tips for this spot in my blog: FAMOUS TAMOLITCH BLUE POOL IN OREGON: AN ANCIENT TURQUOISE GEM

6. Sparks Lake

This is a favorite of mine! There is something incredibly special about sunrise here, and I recommend sunrise because of the crowds. This is a drive up spot and is just outside of Bend, Oregon. Read all of my photo tips, camping advice and more on blog: SPARKS LAKE PHOTOGRAPHY GUIDE: FREE CAMPING & SUNRISE

7. Umpqua Hot Springs

I mean, who doesn’t love a hot springs trip! This is a very crowded and fragile spot, so I STRONGLY recommend you read my entire blog post about it have the best visit possible. Blog: UMPQUA HOT SPRINGS IN OREGON: WHAT YOU NEED TO KNOW

8. Toketee Falls

On the same road as Umpqua hot springs, this is a stunning waterfall featuring Basalt cliffs and blue water. The trail is .9 miles round trip. Get more details at AllTrails .

9. Crater Lake National Park

My visit to Crater Lake was brief, but this view was worth the stop. Did you know Crater Lake is the deepest lake in the USA at 1,943 ft ?! Drive up to the Crater Lake Lodge and hang out near the fire. Just down the parking lot is this view!

Shop My Road Trip Essentials!

10. Samuel H. Boardman State Scenic Corridor

There are so many incredible places to see along this scenic stretch. Natural Bridges, Secret Beach and Whaleshead beach are among my favorites. Check out my full blog for all the details: 6 BEST PHOTO SPOTS ON THE SOUTHERN OREGON COAST

11. Sharkfin Rock at Gold Beach

This place was a happy accident for me. It was sunset, so I pulled off to the nearest beach access to watch the sun go down, and this spot was stunning. I love the rock formations on the Oregon Coast. This location is linked in the blog post 6 BEST PHOTO SPOTS ON THE SOUTHERN OREGON COAST

12. Face Rock State Scenic Beach

Speaking of weird rock formations, this place wins in my opinion. Get a view from up top, or take the stairs down to the beach to see all of the wild rock formations. Detailed information in my blog 6 BEST PHOTO SPOTS ON THE SOUTHERN OREGON COAST

13. Oregon Dunes National Recreation Area

Running down dunes takes me back to my childhood. The Oregon dunes are one of the largest areas of coastal sand dunes in the world! Get more details on my Blog post: 5 THINGS TO DO IN BANDON, OREGON FOR A WEEKEND

14. Oswald West State Park

I LOVE the dramatic cliffs on this coastal spot. Use AllTrails to find some incredible places to explore for the day.

15. Cannon Beach

Cannon Beach is classic, and an awesome way to end your epic Oregon Road trip. I definitely recommend viewing Haystack rock as seen in the picture and relaxing with a picnic on the beach.

More Nearby Destinations!

If you’re looking for more Pacific Northwest Adventures check out these other guides:

Conclusion:

I hope this gives you some road trip inspiration! There are endless places to explore in Oregon. This road trip itinerary requires a decent amount of time, but really allows you to see the most of Oregon. If you’re looking for shorter trips, check out some of my guides linked above or in the Oregon section of the Destinations Tab!

What’s on your Oregon Bucketlist?

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I love a good road trip article, especially a USA one. After reading your post, I really want to go to Oregon and see some of that beautiful scenery. i’ve pinned this for some future travel planning.

Thanks so much! Oregon is one of my favorite states to explore in the USA!

I use to live in PDX…. and let me just say that I hope anyone who’s looking for the ultimate Oregon road trip find your blog! I was so happy to see Umpqua on the list, the place is just magical.

Ahh that means so much!! There are endless things to explore in Oregon!

I’m planning a trip to Oregon for my 50th birthday. Approximately how long is this road trip? I’m starting in Washington and driving down the Oregon coast.

It can definitely be flexible. If you were to hit ALL of these spots I’d recommend a bit over a week. But it can absolutely be squished down.

Thanks for your blog about the road trip to Oregon. We have 7 days next week July 7- 14th vacation. We plan to take highway 5 from Sacramento to Oregon and 101 coastal route back. Do you think it is doable? What town do you recommend to stay overnight? We already book a cabin for our 1st night at Manzanita lake of Lassen National Park. Our bucket list has Mt Shasta, some falls, Crater Lake, Klamath Falls, Redwood National state parks, Redwood sky Walk, Astoria. Thank you very much!

Hey!! I hope your trip is starting off good! Astoria will make for a lot of driving, but it is beautiful! It may be tricky to do the coast and cut inland for the falls on that timeline. Let me know if you make that happen!

Wowza! My husband has been trying to sell a trip to Oregon to me for the longest time and I never took it seriously BUT I will now! The waterfalls and seaside cliffs look like something I have to see in real life! Thank you! My husband will be very happy, you converted me with your stunning photos

I love that!!! Well I hope if you go, you have the best time!

OMG! This is the perfect itinerary for Oregon! I only managed to visit Eugene and Portland during a quick 2 day trip there. I’ve always been meaning to go back.

I hope you get the chance to!! There’s an absurd amount of places to explore in Oregon!

Melissa, can you tell me what towns you would suggest we stay in without staying every night. I prefer a two night stay as a base camp and then go out and hit these places on your itinerary.

Hi, how many days would you recommend to complete this loop?

Hello! If you did sunrise and sunset per spot it would be about a week minimum. That’s what I did with this loop. But it could easily be expanded to 2 weeks!

How many days did this take you? Sorry if it was mentioned, I did not see it. Thanks in advance!

Hello! Great question. I did this at a VERY fast pace of sunrise at one location and sunset at the next. I’d say a week is a great place to start at a faster pace. But you could absolutely trim down some of the spots that are a bit more out of the way. I think 2 weeks would be the most ideal to really get to enjoy everything for longer periods of time

Would you recommend this trip to do as female solo trip?

Great post, as I just started planning our Oregon road trip! This is bookmark and I shall be returning for more tips!

You should really go over to Eastern Oregon, that is the best part of our state honestly. It’s STUNNING over there. The gorge, Wallowas, John Day, etc.

I so wish I had a list like this last time I was in Oregon in 2005, granted I had to finish up my fathers affairs so it wasn’t exactly a pleasure trip where I could just go wherever in the week I was there, but I’ve always made it a point to do a mini road trip anytime I’m up there to explore what I can’t usually enjoy (being I live in Texas!). I will definitely keep this for whenever I am finally able to get back up there so I have a new path to take compared to my past trips. Thank you so much for putting this together!

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Oregon , USA · May 4, 2020

Our 7 Day Oregon Road Trip Itinerary

Part of our heart with forever belong to the state of Oregon. Oregon is by far one of the perfect places to road trip. It is home to some of the most amazing mountains, hot springs, lakes, coastline, and waterfalls in the United States.

To help you explore this incredible state, we have put together a comprehensive 7 day Oregon road trip itinerary that includes must see places and camping tips!

Things to Know before you go!

Best Time to Visit Oregon: Summer and Early Fall is the best time to visit Oregon and is considered peak season. Spring, late Fall and Winter may hinder your ability to visit some areas due to snow!

Let’s get started!

Need accommodation ideas for your PNW Road Trip? Check out our blog post on the most amazing Airbnbs in the Pacific North West!

• Day 1: Arrive in Portland/ Cannon Beach/ South Beach State Park
• Day 2: Bandon Beach/ Samuel H Boardman Scenic Corridor/ Brookings
• Day 3: Crater Lake/ Toketee Falls
• Day 4: Umpqua Hot Springs/ Bend
• Day 5: Abiqua Falls/ Silver Falls State Park
• Day 6: Trillium Lake/ Mount Hood/ Lavender Field
• Day 7: Lost Lake/ Rowena Crest Viewpoint/ Multnomah Falls/ Portland

Oregon Road Trip Day 1

First stop: cannon beach..

Cannon Beach is 90 minutes North West of Portland on the Coast of Oregon. This beach is famous for the Haystack Rock formation. The little town is filled with tons of quaint shops and family owned restaurants to explore! This is the perfect way to start your epic road trip!

This is a popular beach for Hollywood films. You might recognize it from Twilight and The Goonies.

Second Stop: Devil’s Punch Bowl.

During low tide in the summer you can follow the coastal trail and actually walk inside of it. However during the fall and winter months the water level rises and this isn’t possible. It was still incredible to see from an aerial view!

Day 1 Accommodation Options:

• South Beach State Park: This incredible state park offers a range of camping options with clean washroom and shower facilities.
• Rent a local Airbnb: We love staying in Airbnb’s when we travel! If you have never rented an Airbnb before, use our code to get $$ of your stay!

Oregon Road Trip Day Two

First stop: bandon beach ..

This is an incredible spot with some of the most unique rock formations that we have ever seen! We

Second Stop: Samuel H Boardman Scenic Corrido r

This is a 12 mile stretch along the coastline and was one of our favorite parts of our entire trip. You could honestly spend a few days here and still have so much to explore.

Below we put together a list of the most popular stops in this corridor and the approximate mile markers associated with them!

Make sure to write these down before you head here. Some of the stops we listed aren’t mentioned on roadside signs!

Mile Markers for the Samuel H Boardman Corridor

• Arch Rock (Mile 344.8)
• Spruce Island (Mile 345.0)
• Thunder Rock Cove (Mile 345.8)
• Natural Bridges (Mile 346.0)
• North Island (Mile 347.4)
• Thomas Creek Bridge (Mile 347.8)
• Indian Sands (Mile 348.6)
• Whaleshead Viewpoint (Mile 349.3)
• House Rock Viewpoint (Mile 351.2)
• Cape Ferrelo Viewpoint (Mile 352)
• Lone Ranch Picnic Area (Mile 352.6)

Third Stop: Brookings

Brooking’s is a small town with a lot of mom and pop style shops and local restaurants. It was also a great place to stock up on some essential items at the Fred Myer (grocery store)!

We ate dinner at Oxenfre Public House in Brookings. Its currently rated the #2 restaurant in this little town and was the Trip Advisor’s Traveler’s Choice in 2020.

Day 2 Accommodation Options :

Harris State Beach Park: This campground was one of our favorites during our entire trip in Oregon. We watched once of the most incredible sunsets on the beach that this campground sits on. They have a wide variety of camping options and clean washrooms with showers. For more information on booking here, check out this link!

Oregon Road Trip Day 3

This day was the most action packed day of our entire trip!

Start by taking Highway 199 Scenic Byway which leads you through one of the most scenic drives in the USA.

This highway passes through the Jedediah Smith Redwoods State Park . This is an incredible opportunity to see some of the most beautiful trees in the world.

First Stop: Crater Lake

Crater Lake National Park is a bucket list place for many. The water of the lake is an incredible color of blue. There are so many things to do here, we have listed some of our favorites below!

Things to do at Crater Lake:

• This hike is one of the most popular hikes in the park. It leads to a fire lookout. This trail takes about 1 hour round-trip and is the best place to catch the Sunset.
• This trail is 2 miles in length and traces the rim of Crater Lake. This trail is relatively easy to do and offers some incredible perspectives on the lake.
• A hike down to Cleetwood Cove with lead you to the only spot at the lake that you can swim! The water temperature ranges from ranges from 0°C to 19°C so on a hot day it will be refreshing!

Stop Two: Toketee Falls .

There is a small parking lot at the trailhead. The 0.8 mile hike to the main lookout point was very easy and incredibly rewarding. To get to the viewpoint in our photo below, you have to climb down from the main path to the

Day 3 Accommodation Options:

• Toketee Lake Campground : This is a rustic campground with very basic amenities. This campground does not have running drinking water, so make sure to bring plenty with you! They also only have outhouses and they do not have showers.
• Luxury Glamping Tent: This Airbnb is a glamping resort located just a short drive away from Toketee Falls and Crater Lake. There are fire rings, washrooms and showers available here! Check out their link here!

Oregon Road Trip Day 4

F irst stop: umpqua hot springs.

Located only a few minute drive from Toketee Campground, this is the perfect way to start the morning.

Tips for visiting Umpqua Hot Springs:

• Arrive early in the morning to avoid any crowds. We got there at 7:30 and we had to all to ourselves for over an hour!
• It is a 0.8 mile hike to the Hot Springs from the parking lot. Make sure to wear running shoes as it is a moderately difficult trail.
• There are bathrooms at the trailhead but there are none once you reach The Hot Springs themselves.
• Nudity is acceptable at Umpqua so be prepared and be respectful when taking photos.

Second Stop: Bend

The city of Bend is an outdoor lover’s paradise and a craft brewery mecca. There are over 22 breweries in Bend! Bend has a beautiful downtown filled with local shops and restaurants right along the river.

Some of our favorite places in Bend were:

• Get here early as it fills up fast. This is possibly the best breakfast you will ever have.
• Located along the river, they have indoor and outdoor seating as well as lawn games!
• Cascade Lakes Brewery
• Dudley’s Bookstore and Cafe
• The Bend River Wave
• People from around the world travel here for skiing in the winter and mountain biking in the summer!

Accommodation Options Bend:

• Stay at the Loge: This hotel was completely renovated and is one of the most popular spots in Bend. All rooms come equipped with hiking and camping gear that is free to use during your stay! They also have free city bikes that we used to explore Bend, as well as fire tables and a cafe!
• Dome Airbnb: This Airbnb is seriously so unique and is in a great location! Check out their link here!

Oregon Road Trip Day 5

First stop: abiqua falls.

We left Bend very early in the morning as it is approximately a 3 hour drive to the Abiqua Falls Trailhead. This trail is a 5.3 mile out and back from the trailhead itself.

Reaching the trailhead can be tricky as the road can be washed out at times, leaving large potholes that are difficult to navigate around. We drove as far as we could down the road (considering we were in a rented campervan) and then decided to walk the rest of the way.

This trail is rated as difficult as it is very muddy and requires the use of ropes to navigate in some sections. This hike was incredible and Abiqua Falls is unlike anything we have ever seen before. You HAVE to hike this.

Second Stop: Silver Falls State Park

We hiked the Trail of 10 Falls, which is a 7.6 mile loop trail that features 10 incredible waterfalls and is the most famous trail in the park.

Day 5 Accommodation:

Silver Falls State Park: The campground here is beautiful and the facilities are well kept. This was the perfect place to spend the night! It is also close to all of the hiking trails which makes exploring this State Park very easy.

Oregon Road Trip Day 6

First stop: mount hood area.

Things to Do in the Mount Hood area:

• A beautiful lake with the stunning backdrop of Mount Hood
• If you are visiting Mount Hood in the winter time, this is an incredible and bustling Alpine Village.
• This is the famous hotel featured in the movie The Shinning
• This Lavender Farm offers some of the most picturesque views of Mount Hood
• Make sure to check their Facebook Page for their hours and operating months.

We then attempted to visit the Lavender Valley close by but unfortunately it was closed… so we took this photo across the street from the Lavender Field!

Day 6 Accommodations

Lost Lake Campground: This campground is set on the shores of Lost Lake, and offers some incredible adventures and beautiful views of Mount Hood. They have Yurts, Lodge Rooms and campsites available making this an experience for everyone! Check out their website here.

Oregon Road Trip Day 7

Stop one: lost lake campground.

We decided to rent a paddle boat right after sunrise and we took in some incredible views of Mount Hood from the lake.

After our morning on the lake, we decided to head back towards Portland where we stayed the night before flying back home!

Second Stop: Rowena Crest Viewpoint

This is one of the most photographed roads in the state of Oregon and offers incredible views of Columbia River and the State of Washington.

Third Stop: Multonomah Falls

This is one of the most photographed places in the State of Oregon. We recommend getting here early in the morning prior to the tour buses as this place can get busy quick.

Fourth Stop: Mississipi Ave, Portland

This street was SO MUCH FUN! Tons of local restaurants, outdoor and indoor bars and little locally owned shops. We spent the entire afternoon and evening exploring this street and all it had to offer. We highly recommend this spot if you are looking to stay out of downtown Portland.

Things To Add To Your Oregon Road Trip

As we said earlier, we only had 7 days to pack in as much activity as we possibly could. That being said, there are so many things left that we didn’t get to see. When we return we want to visit the Painted Hills, Smith Rock State Park, more amazing hot springs, more waterfalls and explore more of the Columbia River Gorge.

Final Thoughts

We love Oregon. We will be returning to continue exploring all of its incredible magic someday. If Oregon is not on your bucketlist, it needs to placed on there immediately. This state is unlike any place you will ever visit in your life. It has such a unique set of landscapes. From gorgeous coast lines, hundreds of powerful waterfalls, vast desert and tall mountains, this place really has it all!

We hope that you found this blog post helpful! Let us know in the comments below if you have been to Oregon and what your favorite places were!

Happy Travels 🙂

Jake and Kaylee

before you leave…

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May 6, 2020 at 3:43 pm

We love this! We have been planning a road trip through here and we’re making a list. This was super helpful! Thank you for sharing

The Lovers Passport

May 6, 2020 at 9:31 pm

Thank you so much for the comment! We love hearing that what we write is helpful. We hope you guys have an epic adventure through Oregon! Keep in touch and let us know where you went!

– Jake + Kaylee xo

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Marin Olivia

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8 Days in Oregon – The Perfect Road Trip Itinerary

September 13, 2022 · In: Travel , Travel Guides

If Oregon has been on your bucket list of travel destinations but you don’t know where to start, look no further because I spent hours researching before executing the perfect road trip itinerary. We packed a lot into our one-week (8-day) trip and I’ve outlined all of the travel itinerary details below.

Oregon Road Trip

Travel itinerary.

• Beaverton / Willamette Valley
• Willamette Valley
• Oregon Coast
• Crater Lake / Bend
• Hood River / Portland

Road Trip Day 1 – Portland

Our first day was a travel day but we were fortunate enough to have an early flight that allowed us almost a full day of exploring. Step one for our Oregon road trip was to get a rental car but step two was definitely to get some of the incredible food and drinks Portland has to offer.

What to eat and drink:

• Tusk – This is number one for a reason! A must go if you love Mediterranean food.
• Screen Door Pearl District
• Multnomah Whiskey Library – The Green Room
• Deschutes Brewery – Portland Public House

Where to stay:

• The Bidwell Marriott Portland

What to do:

• Visit Powell’s Books
• Explore the city! There are so many great shops and a bonus of no sales tax.

Road Trip Day 2 – Beaverton / Willamette Valley

I organized the Oregon road trip itinerary counterclockwise so the next stop in the loop was to head towards Willamette Valley. On our way there we stopped in Beaverton to see a friend.

• Tom’s Pancake House (Beaverton)
• Central Station Taps (Beaverton)
• Red Hills Market (Dundee)
• The Setting Inn (Willamette Valley)
• Tour Nike Headquarters (Beaverton) – If you’re lucky enough to know an employee I highly recommend.
• See a movie (Newberg)
• Wine tasting! – More on this in Day 3.

Road Trip Day 3 – Willamette Valley

I definitely recommend allowing at least one full day to enjoy wine country. We were able to fit in two wine tastings + lunch and dinner which I felt was a good amount to fit in one day without feeling rushed. Plus, now we have an excuse to come back again to try more.

• Field + Stream (Dundee)
• Trellis (Dundee)
• Penner Ash 60 min tasting
• L’Angolo 90 min tasting

Road Trip Day 4 – Oregon Coast

There’s just nothing quite like driving down the Oregon Coast! Our goal was to hit some of the major scenic viewpoints as we made our way south and the views did not disappoint.

• Pelican Brewing Pacific City Brewpub (Pacific City)
• Ben and Jeff’s Burgers and Tacos (Pacific City)
• The Drift Inn and Restaurant (Yachats)
• Bay Point Landing (Coos Bay)
• Cape Kiwanda (Pacific City)
• Devils Punchbowl (Otter Rock)
• Yaquina Head Lighthouse (Otter Rock)
• Thor’s Well (Yachats)
• Cape Perpetua (Yachats)

Road Trip Day 5 – Oregon Coast (Coos Bay)

We had an extra day on the coast scheduled in our Oregon road trip so we explored some of the state parks clustered within the Coos Bay area. The rock formations were incredible and the Pacific Ocean is gorgeous.

• The Grounds Cafe (Coos Bay)
• 7 Devils Waterfront Alehouse (Coos Bay)
• Shark Bites Cafe (Coos Bay)
• Oregon Dunes National Recreation Area , John Dellenback Trail
• Shores Acres State Park
• Cape Arago State Park
• Sunset Bay State Park

Road Trip Day 6 – Crater Lake / Bend

Get your podcasts ready because this day was the longest day of driving. Throughout my Oregon road trip research I was wavering between whether or not Crater Lake was worth the drive, but after seeing it in person I can say it is 100% worth it. Photos do not do it justice.

• Drive through The Grounds Cafe (Coos Bay) before hitting the road
• Lunch on the road (we found a Subway) or Crater Lake Rim Village Cafe
• Dinner at Wild Rose (Bend) – This deserves its own blog post it is that good!
• We were lucky to be visiting and staying with a friend but if we didn’t I would look into Marriott SpringHill Suites Bend .
• Drive around the lake
• Stop at Vidae Falls

Road Trip Day 7 – Bend

Bend was probably my favorite stop on the trip and we spent most the day paddle boarding on Elk Lake. It was a perfect day and I can’t wait to go back to explore all that Bend has to offer.

• Bo’s Falafel Bar
• Boss Rambler Beer Club
• Wild Rose – Again, worth repeating it is so good.
• The Bob Bend (food cart)
• Nancy P’s Cafe and Bakery
• Deschutes River
• Drake Park – There was a Munch & Music going on when we visited
• Paddle board on Elk Lake

Road Trip Day 8 – Mt. Hood / Hood River

For the last full day or our Oregon road trip itinerary we made our way up to Mt. Hood, Hood River, and then traveled through Columbia River Gorge back to Portland. You could spend full days at all of those locations so definitely keep in mind that we only barely scraped the surface on this day.

• PFriem (Hood River)
• Sugarpine Drive-in – We wanted to stop here on our way from Columbia River Gorge to Portland but it was unfortunately closed.
• We ended our epic Oregon road trip itinerary back in Portland and stayed at the Moxy Portland Downtown for a quick drive to the airport in the morning.
• Trillium Lake (Mt. Hood)
• Timberline Lodge (Mt. Hood)
• Hood River Lavender Farms (Hood River)
• Multnomah Falls (Columbia River Gorge)

That’s a wrap for our Oregon road trip itinerary! Please let me know in the comments if you have any questions. Any recommendations I missed?

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My name is Marin and I am a twenty-something living in Milwaukee. My day job is as an advertising Account Supervisor managing my portfolio of clients’ plans and business goals. In my free time I am growing and pursuing my passion for content creation, training and loving my pup, Jarvis, and planning my next adventure.

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