best new england travel itinerary

New England Wanderlust

Connecticut , Fall , Maine , Massachusetts , New Hampshire , Rhode Island , Vermont  ·  June 7, 2023

The PERFECT New England Fall Road Trip Itinerary: 3, 5, 7, 10 & 12 Day Options! (2024)

There’s a reason why New England is world-famous for fall foliage, and if you’re looking to plan the most amazing New England fall road trip, you’ve come to the right place! I’ve been traveling throughout this region for over 15 years, and have done quite a few fall foliage road trips and even more fall getaways. It took me a while, but I’ve finally put together the perfect itinerary for you based on real experience.

This post details the best places to visit in New England during fall foliage season that are worth the hype, the best times to plan your road trip, and also, which places may not be worth your time. So, you can rest assured that you’re truly seeing the best of the best with my itinerary.

This itinerary is also geared toward first-timers and those looking to find the best foliage spots . If you’ve experienced New England in the fall season before, many of these locations and tips may already be familiar. However, I’ve also sprinkled in some insider tips, so it’s still definitely worth reading 😉

During this trip, prepare to see idyllic countryside landscapes, blazing fall color, beautiful covered bridges, charming towns, general stores, epic overlooks and hiking trails, and so much more. Basically, you’ll get your fill of New England charm right from the start, and it won’t stop until the trip is over. Sound good? Then let’s get started!

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Tips For Planning A Trip To New England In The Fall

There are some important things to know before you begin to plan your perfect New England fall road trip, so let’s get that out of the way first 😉

The first thing you need to know is that foliage will peak in the northern areas first, then peak in the southern areas later . For that reason, I recommend that you start in the north if you can, especially for a longer trip, but it’s not always necessary for shorter trips.

If you’re planning a bucket list 2-week adventure, starting in the north is a good call because peak foliage can begin to diminish quickly, depending on the season and climate patterns. However, if you’re traveling for closer to a week, this won’t be as important.

I go into peak foliage times in each region in a bit, so definitely be sure to read that through, too!

Another important thing to know is that you should anticipate all kinds of weather. I’ve done many fall road trips through this region, and have had warm, sunny days, and trips where it rained almost every single day. I’ll go more into what to pack for this trip at the end of the post to help you prepare, but this is a good thing to be aware of.

Also, book in advance . I can’t stress this enough. Hotels and accommodations book out well in advance for fall foliage season in prime areas, and these prime areas are where you’ll be heading! If possible, begin to book your hotels at least 6 months in advance, but even 8 months is better. For reference, while I began to plan my Vermont fall road trip for the 2023 season, my favorite place to stay in Stowe, VT was fully booked during peak foliage weeks – in FEBRUARY. Yep, February.

Offline Google Maps! I can’t tell you how important this is! Even as recent as a fall 2022 road trip, I barely had service through much of New Hampshire and Vermont. I spent a lot of time just driving around hoping my service would come back, or asking people for directions the old-fashioned way. I usually offline maps, but totally forgot that trip, and it was a harsh reminder that this is a must-do.

Lastly, prepare to pay . Yes, the sad truth is that peak foliage season in New England is expensive, and it won’t be your most budget-friendly trip ever. There are ways to keep costs down, and I’ll go more into that later in the post as well, but generally speaking, this is an expensive time to visit New England – at least, where the foliage is the best 😉

What Is The Best Time To Visit New England For Fall Color?

In a nutshell, the last week of September, or the first week of October. However, it does vary depending on where you’re heading.

As mentioned before, the colors will begin to change in the northern regions first, and then the southern regions will follow later. Most people will choose to visit Maine, New Hampshire and Vermont during their New England fall road trip (and spoiler alert: this is also where I’ll be suggesting you go!), so this timeframe works very well for these areas.

The central part of Vermont will often peak right around Indigenous People’s weekend in October, and for a getaway to popular towns like Stowe and Woodstock, this is the perfect weekend to plan your trip.

Massachusetts often peaks right around Indigenous People’s weekend as well, with southern MA peaking a week or so later.

The greater Boston area, and Connecticut will peak mid-late October, depending on the year.

How Many Days Do You Need In New England In The Fall?

The great thing about New England in the fall is that you can easily do a weekend getaway and still pack a lot in, or you can plan an epic 12 day road trip for the ultimate adventure. And either way, it’s going to be incredibly memorable.

If you’re coming in from a distance, especially if you’re flying in, I would say 10 days is a great option, 12 days is even better, and 7 days is also wonderful. Of course, with 12 days, you’ll be able to see so much or plan extra time in some places. But even with 7 days, you’ll get to see quite a bit.

If you’re local to New England, and don’t have 10 days, 7 days is again a nice sweet spot. 5 days will also work in this case. And, as mentioned, even a weekend away will allow you to experience some of the best this region has to offer in the fall season.

The great thing about the best places for fall foliage are located in some of the smallest states, so you can cover a lot of ground in a short amount of time.

Best Places To See On A New England Fall Road Trip

While every New England state has something special to offer during fall foliage season, for the purpose of seeing the absolute best spots, I recommend sticking to Maine , Massachusetts , New Hampshire and Vermont . And flying into Boston.

Because these areas offer the most spectacular displays of foliage, most picturesque scenery, tons of things to do, and they’re all reasonable close to one another, allowing you to maximize your time.

Here’s why I don’t necessarily recommend states like Connecticut or Rhode Island if you have less than 10 days – they’re further away from the best places to see in the fall.

I truly love every single New England state, and I do really enjoy Connecticut in the fall. However, it’s so far west that you’ll spend more time driving to get there, and possibly forgoing some really spectacular places in Maine, New Hampshire, Massachusetts, and Vermont.

If you have 10 days or more for a New England fall road trip, then I would highly suggest you consider adding in the Litchfield Hills regions of Connecticut , which you’ll see I included in my itinerary. It’s also very close to The Berkshires region, so you can combine it with that part of the trip, depending on how much time you have. However, with less than 10 days, I personally don’t feel like it’s worth it. Especially for first-timers.

If you’ve already seen some of the places I’m recommending in this post, then definitely try to swing over to Connecticut and experience a new area during the fall!

If you have less than 10 days, you may even want to focus all your time on Vermont and New Hampshire. The reason for this is because some of the best places for fall foliage in Maine are further north. I think places like Acadia National Park are very worth seeing (and you’ll see I’ve incorporated it into some of my itineraries!). However, if you prefer a slower pace and less driving, Vermont and New Hampshire are the absolute best places to see .

Some Things To Know About My Itineraries

They all begin in Boston , assuming that’s where most people will fly into if visiting from a distance. If you fly into a different airport, or are driving in, you can easily adjust your plans as needed.

They’re done in true road trip style , meaning there’s a lot of driving, and mostly 1-night stays. There are some places I recommend 2 nights in, but you can adjust this based on your preferences. If you want to stay longer in one place, definitely go for it!

I give you options! Of course, I stand by all my suggestions ☺️ However, I know everyone has different travel styles and speeds, so I encourage you to to tailor this to what you think you’ll enjoy the most. I’ve given you suggestions on how to adjust the itinerary based on your preferences.

10 Day New England Fall Road Trip Itinerary From Boston

Okay, let’s get into my perfect New England fall road trip itinerary options! We’re beginning with my suggestions for an incredible 10 day adventure.

10 Day Road Trip Overview

Day 1 : Arrival In Boston Day 2 : Explore Boston Or Take A Day Trip To Salem Day 3-4 : Bar Harbor/Acadia National Park + An Optional Stop In Salem Day 5 : Jackson, NH Day 6 : Franconia, NH (Driving The Famous Kancamagus Highway To Get There!) Days 7-8 : Stowe & Woodstock, VT Day 9 : The Berkshires and/or Litchfield, CT Day 10 : Back To Boston + A Stop In Sturbridge, MA or Litchfield, CT

Breakdown Of The 10 Day Itinerary Option

Day 1: Arrival In Boston Take this time to arrive, get settled, and maybe take in a few sites around the city! Have some time on your first night here? Jump down to Day 2 for some suggestions on what to do!

Where To Stay In Boston:

• Luxury : The Langham
• Splurge : Boston Harbor Hotel
• Moderate : Revere Boston Common

Pro Tip On Fall Foliage In Boston : Foliage peaks later than the rest of the places listed in this itinerary – usually mid-late October. So while you probably won’t see peak foliage in Boston if you plan your trip for peak foliage in Vermont, New Hampshire and Maine, it may catch a glimpse of it on your back if you’re planning a longer trip! Or, you can leave the airport to immediately begin your drive to Maine, and plan to stay a night or two in Boston before you have to fly out.

Day 2: Explore Boston

Boston during the fall season has so much to see and do, but here are some highlights to consider if it’s your first visit:

• Public Gardens (very scenic garden area with a beautiful pond and pedestrian bridge (also makes for lovely photos!). This is a good spot for fall foliage in the city, too.
• Newbury Street for shopping
• The North End for history and food
• Beacon Hill for charming cobblestoned streets at the famous Acorn Street
• Take a food tour if it works with your schedule. There’s incredible food to be had in Boston, and taking a tour with a local expert is a great way to sample lots of delicious things in a short amount of time!

Click here to check out my post on the best Boston food tours!

Day 2: Optional Day Trip To Salem

If you would prefer to take a day trip to Salem, rather than stopping on your way to Acadia National Park, this is a great option! And really, there’s no right or wrong choice here – it just comes down to which you prefer.

Salem is an easy day trip from Boston without a car because of this convenient ferry! Click here to check out the Boston → Salem Ferry!

Psst! I have some helpful guides including planning the perfect Salem, MA day trip , and the best time to visit Salem if you need more information 😉

Day 3: Drive To Bar Harbor & Acadia National Park

Acadia National Park is one of the best things to do in New England year-round, so this is definitely a must if you’ve never been. It also offers some really wonderful foliage, and fall is my personal favorite season to visit for this reason.

This drive from Boston to Bar Harbor takes about 5 hours without stops, which is why I usually suggest you make a pitstop to break up your journey. I actually have some posts on stops you can make along the drive, so be sure to check those out below.

But since Salem is really the ultimate fall destination in Massachusetts, I suggest you pick that as a stop on the drive 🙂

Bar Harbor is the town adjacent to Acadia National Park , and where most people will choose to stay when visiting. Once you arrive, take some time to get settled, and then head out into downtown Bar Harbor to explore this charming seaside town, visit the shops, and grab a great dinner!

Where To Stay In Bar Harbor:

• Bayview Hotel . An oceanfront boutique hotel with awesome views. Perfect for a splurge on your trip!
• Bar Harbor Villager Motel . Clean, updated and spacious. Also, walkable to everything in town.
• Little Fig Hotel . A cute, modern boutique hotel walkable to town.

Here are some posts that will help you further plan this portion of your trip:

• Best Stops To Make Driving Boston To Portland, Maine
• Best Stops To Make Driving Portland to Acadia National Park
• The Perfect Acadia National Park Itinerary (read this one for more information on Bar Harbor and things to do!)
• Best Time To Visit Acadia National Park

Day 4: Explore Acadia National Park

Even in just 1 day, you can visit some of the best places in the park, and also some really wonderful fall foliage spots. Here how I suggest you plan your day:

If you’re up for it , starting your day with sunrise at the top of Cadillac Mountain is always incredible! It’s one of the first places in the U.S. to see the sunrise, depending on the time of year, and starting October 7 through March, it’s the very first spot in the country to see the sun come up. This will be great for fall foliage, too. You can also choose to do this the following morning before leaving.

Next, head to the Jesup Path scenic walk , which is especially beautiful in the fall season.

Then, park at the Sand Beach parking lot , and walk the Ocean Path for incredible views . This is 1-mile each way, but offers some of the most iconic views in the park, including the Otter Cliffs and Thunder Hole. It’s also flat and easy, making it very relaxing. Have your camera ready for this one!

For a more advanced hike with awesome foliage views, you can do the Beehive Trail from Sand Beach lot, too.

Continue on Park Loop Road to Jordan Pond House for lunch , and enjoy the views of the pond and mountains. You can also choose to walk around the pond if you have time after lunch.

For more foliage views, hike the Bubble Rock Trail after lunch.

Day 5: Drive To Jackson, NH + Spend The Night

Without stops, this drive takes about 4 hours and 15 minutes.

One stop I suggest making on the way if you enjoy local craft beer is the Oxbow Beer Garden in Oxford , ME . It’s got a very cool outdoor setting, and they have fantastic craft beer.

I recommend spending the night in Jackson because it’s a longer drive from Bar Harbor, and there are some fun things to do in the area. Also, there’s a very scenic drive called The Kancamagus Highway that’s stunning in the fall season with foliage, and I want to make sure you have time to drive it. But more on that in Day 6 🙂

Here are some fun fall things to check out in Jackson:

• The Cog : This mountain railroad takes you to the summit of Mount Washington, the tallest peak in New England! It’s about 45 minutes from Jackson, but you’ll drive through Crawford Notch State Park , which is very scenic, and The Cog is simply incredible in the fall season. If you leave Bar Harbor early enough and have time to do this, I highly recommend it!
• Honeymoon Covered Bridge & Flossie’s General Store
• Glen Ellis Falls
• The cute town of North Conway

Where To Stay In Jackson:

• Christmas Farm Inn (this place is super cozy!)
• The Inn At Thorn Hill & Spa

Option To Stay In North Conway : North Conway is only about 12-15 minutes from Jackson, so you can really stay in either. I think Jackson has better hotel options, and it’s a bit closer to The Cog, which is why I suggested you stay there. But either town works for your New England fall road trip!

Here are some fun things to check out in North Conway if you choose to visit:

• Cathedral Ledge Distillery
• Ledge Brewing Company (between North Conway and Jackson, technically)
• The cute downtown area and Zeb’s General Store (one of my all-time favorite general stores!)
• North Conway Scenic Railroad

Day 6 – Drive The Kancamagus Highway To Franconia, NH

The Kancamagus Highway (Route 112) is a scenic drive that’s regarded as one of the best drives for fall foliage, so this is something you’ll definitely want to do on your New England fall road trip. It connects the towns of Woodstock and Conway, so you can easily start this drive just a few minutes from Jackson or North Conway.

For this day, I suggest you get up early to make sure you have time to explore Franconia Notch State Park after driving The Kanc.

Tips For Driving The Kanc:

• Remember earlier in the post when I said you’ll lose cell service in much of New Hampshire and Vermont? Well, this is one of those drives where there’s no service, so offline your maps before starting!
• There are no bathrooms or gas stations on the drive, so plan accordingly.
• The Kanc takes about 45 minutes one-way without stops, but you’ll want to budget about 2 hours to make some stops at the overlooks.
• During the fall season, especially on weekends, it’s possible traffic could slow down as people try to pull in and out of the parking areas. Plan for some slower traffic.

Pro Tip : Before hopping onto The Kanc, there’s a great little place called Cheese Louise just before the entrance to The Kanc, and this is an awesome place to grab some food before the drive! Especially on a chilly, fall day, a grilled cheese sandwich totally hits the spot, right? 😍

Stops To Make On The Kanc (in order from Conway to Woodstock):

• Albany Covered Bridge
• Rocky Gorge Scenic Area (parking can be found at 44.0016667175862, -71.27716637107925)
• Sabbaday Falls
• Sugar Hill Scenic Overlook
• CL Graham Wangan Overlook
• Hancock Overlook (this one is right at the famous hairpin turn – can’t miss it!)
• Lincoln Woods Trailhead – Scenic suspension bridge over the river that’s not far from the parking lot.

🍁 Before hopping on The Kanc, consider downloading this great audio tour to enhance your drive – Click here to check out this audio tour!

There are also tons of hiking trails along The Kanc , so if you’re looking to squeeze in a hike on the drive, this is something to consider. But if you don’t have extra time, I would suggest moving on to Franconia Notch State Park, and only doing hikes along The Kanc if you’re able to add an extra day in.

After The Kanc, your next stop is Franconia Notch State Park . And this is where most of the top things to do are , especially in the fall season .

Flume Gorge is one thing I recommend you do if you can only pick one attraction. Flume Gorge is a very fun 2-mile loop trail that takes you over 2 covered bridges, and through the granite gorge. Along the trail, you’ll have some really gorgeous spots to admire the fall foliage, too.

Not sure if this is right for your itinerary? Click here to check out my detailed post in if Flume Gorge is worth visiting , and everything you need to know to plan the perfect visit.

Pro Tip: Buy your Flume Gorge ticket online in advance to save a few bucks! On weekends in the fall season, it’s also possible that certain time slots will sell out. This is another reason to book in advance.

If you have time to explore more of Franconia Notch State Park, I also recommend these activities:

• Cannon Mountain Aerial Tramway
• Artist Bluff Trail (famous spot that ends overlooking Echo Lake – amazing during foliage season!)
• The views at Echo Lake Beach

Where To Stay Near Franconia:

• Sugar Hill Inn – 15 mins from Franconia Notch Park, and is rated as the best B&B in New Hampshire!
• Riverwalk Resort – 5-7 mins from the top attractions in Franconia.
• Woodstock Inn & Brewery – Cozy inn with a brewery.

Here are some posts to help you plan this portion of your trip:

• Fun Things To Do In Franconia, NH
• Fun Things To Do In Littleton, NH
• Fun Things To Do In Lincoln, NH
• Where To Stay In New Hampshire In The Fall
• Where To Stay In The White Mountains: Guide To The Towns

Day 7 – Drive To Stowe Or Woodstock, VT

Begin your day in New Hampshire with a country breakfast at Polly’s Pancake Parlor! This place is famous in New England, and truly has some of the most amazing pancakes I’ve ever had. It does get busy in the fall season, but man, it’s so worth it.

Then, on to Vermont you go! For the next 2 nights, you’ll want to choose between Stowe and Woodstock, VT as your home base. These towns are the absolute best to visit in Vermont during a New England fall road trip because of foliage views and small-town charm. They’re only 1 hour and 15 minutes from each other, so, you can choose where you want to stay, and then visit the other as a day trip.

The drive to both Stowe and Woodstock is 1 hour and 30 minutes from Franconia , and since this is a shorter drive, you can make some stops along the way, or drive straight there. Stowe and Woodstock both have a lot to do, even though they’re small towns, so it’s beneficial to drive straight there and make sure you have plenty of time to explore.

If you choose to stay in Woodstock, I suggest stopping at the King Arthur Baking Company campus on your way because it’s pretty much on the direct route. It’s a really fun place with fresh baked goods and breads, a café, and a fun shop where you can stock up on pantry staples and baking mixes.

Do I recommend you stay in Stowe or Woodstock? I honestly love both equally! There’s no wrong choice here.

The biggest difference between the two is that Woodstock feels a bit more upscale, and Stowe definitely has a very casual feel to it. But the difference is minor. Both have charming covered bridges, great shops, amazing restaurants, a quaint town feel, and plenty of things to do.

Where To Stay In Stowe :

• The Green Mountain Inn . It’s located right on Main Street, so you can walk to a lot of places.
• Spruce Peak Resort . Perfect for those wanting a resort feel, and it’s right off the scenic Smugglers Notch drive. There are rooms with gorgeous mountain views here, too.

Where To Stay In Woodstock :

• The Woodstock Inn & Resort . It’s referred to as Vermont’s most beautiful address, and it’s in the heart of Woodstock’s village. This is a luxury hotel that’s worth it!
• 506 Inn On The River . Located just outside of the village, this is a modern and cozy inn, well … right on the river 😉

Here are some posts that will help you plan your time in Stowe and Woodstock:

• Best Things To Do In Stowe
• Best Things To Do In Woodstock

Day 8 – Explore Stowe & Woodstock, VT

Depending on where you stay, you’ll want to take a day trip to the other town this day. Below are breakdowns of the can’t miss things to do in each town .

Best Things To Do In Stowe :

• Explore the cute shops along Main Street (don’t skip the Stowe Mercantile!)
• Drive Smugglers Notch for amazing foliage.
• Ride the gondola to the top of Mount Mansfield, the highest peak in Vermont (this is epic during the fall season!). This is located at the midway point along the Smugglers Notch drive.
• Visit Emily’s Covered Bridge, and learn about it’s spooky history.
• Sample the hard cider at Stowe Cider.
• Sip on craft brews at Alchemist Brewing (one of my favorites in New England).

Best Things To Do In Woodstock:

• Stroll through the charming downtown shops and eateries.
• Pop into Mon Vert Café for a warm drink.
• Snap a photo with Middle Covered Bridge in town.
• Drive over Taftsville Covered Bridge to visit Sugarbush Farms. You’ll be able to sample homemade cheese and fresh maple syrup here, and also take in amazing foliage views.
• Visit Billings Farm & Museum.
• Drive over to Sleepy Hollow Farm to see the famous farm landscape spot.

Day 9 – Drive To The Berkshires Or Litchfield, CT

Next up – The Berkshires or Connecticut! This choice is yours entirely. Let’s start with the option to drive to The Berkshires.

The Berkshires is an iconic region in Massachusetts that’s a really great one to visit for fall foliage. Here, you’ll find cute towns, loads of fall color, lots of scenic hikes and walks, and awesome dining options.

Depending on which town in Vermont you’re coming from, the northern region of The Berkshires area will be just over 2 hours from Woodstock, or just over 3 hours from Stowe .

The drive from either town to The Berkshires will pass through Rockingham, VT, and you’ll definitely want to stop here to visit the Vermont Country Store! There’s also the very cute Kissing Covered Bridge here that makes for a fun photo.

Once you arrive in The Berkshires, I suggest you start in Williamstown, and drive the scenic Route 7 down to Sheffield. This drive without stops takes about 1 hour and 15 minutes, but I would budget at least a few hours to make stops and enjoy some other fun activities. This route packs a lot into a perfect fall day, without a lot of driving.

During this drive, these are the best stops to make:

• The Mount Greylock Auto Road to the highest peak in Massachusetts (absolutely amazing in the fall season!).
• Make a detour off Route 7 to Bartlett’s Orchard in Richmond for the perfect fall farm experience.
• Continue with your short detour to Hilltop Orchards, which is 5 minutes from Bartlett’s, and where you can sip on artisanal craft ciders!
• Walk through the charming town of Lenox.
• Stroll through quaint Stockbridge, too!
• Snap photos with the covered bridge in Sheffield.

Where To Stay In The Berkshires:

• The Red Lion Inn . A historic and famous inn in the heart of Stockbridge.
• The Dewey . A cozy, traditional New England B&B in Lenox.

The other option is to drive to Litchfield, CT , which is south of The Berkshires. It’s a longer drive from Vermont, but you could also turn this into a fun road trip day by driving the same Route 7 itinerary as mentioned above through The Berkshires, and then continue on to the Litchfield Hills. I would probably only choose this option if you wanted to take your time exploring the awesome stops along Route 7 in The Berkshires, arrive in CT in the evening, and then explore this region of CT the next morning before your drive back to Boston.

How To Spend Your Time In Litchfield Hill, CT:

Since you’re likely coming down through the western border of Massachusetts, I would start in Kent, and work your way east. You probably won’t have time to do everything on this list, but pick and choose based on your preferences and schedule.

• Explore the cute town of Kent, and then visit Kent Falls State Park if you have time.
• Continue to follow Route 7 to New Milford. The drive is very scenic!
• Stop in New Milford to enjoy the quaint town, and then visit Lover’s Leap Bridge.
• Head over to Washington, and then continue on to Mount Tom State Park for awesome foliage.
• End in the charming town of Litchfield.

Where To Stay In The Litchfield Hills : Litchfield Inn . Refined and still very cozy, and one of the best in the area!

Should I do The Berkshires or Litchfield, CT? Personally, I would stay stick to The Berkshires since this will allow you a more relaxed itinerary. There’s so much to do, and plenty of foliage scenery to take in. If you do the Route 7 drive quicker than you were anticipating, you could always shoot down to the Litchfield Hills for an impromptu adventure 🙂

I would choose to add on the Litchfield Hills if you’re feeling adventurous, and really want to see as much of New England as possible.

Day 10 – Drive Back To Boston, Stopping In Sturbridge or Litchfield On The Way

If you have time to explore another cute town on your drive back to Boston, I would suggest either tacking on a quick drive through the Litchfield Hills, CT if you didn’t already, or a stop in Sturbridge, MA. Sturbridge is more on the way to Boston, and offers beautiful foliage.

How to spend your time in Sturbridge, MA :

• Visit Old Sturbridge Village for all the cozy fall New England vibes (this is a must if you have time!).
• Pop into Saw Dust Coffee & Dessert Bar for lunch and treats.
• Sip on craft beer at Altruist Brewing Company.

And of course, as mentioned in the previous day’s itinerary, the Litchfield Hills region has plenty to offer for foliage views, small towns, and beautiful scenery.

But, if you have a flight to catch, then don’t risk it, and head straight to the airport! 🙂

Optional Adjustments For The 10 Day Itinerary:

• You can easily cut out Acadia National Park, and head straight to New Hampshire, and choose to spend more time there. Acadia is out of the way, and further north, so I know it doesn’t suit everyone’s plans. This would allow you time to definitely ride The Cog, and have a more relaxed schedule.
• If you would rather have more time in Vermont, you can skip The Berkshires/CT. This is personal preference! Both areas are amazing for fall foliage, but nothing is quite like Vermont in the fall. This would allow you time to move at a slower pace. If you decide to skip The Berkshires/CT and stay in Vermont for a third night, see my 12 day itinerary, option 3 for suggestions on what to do!

12 Day Road Trip Itinerary Option

If you have 12 days (or more!), this is truly awesome. I would follow my 10 day itinerary, and then take one of these suggestions:

Option 1 : Add in 1 day to see Litchfield, CT after The Berkshires . Since you have the extra time, you can definitely see the Litchfield Hills region of Connecticut with this itinerary! I would recommend this option for those who really want to see as much of New England as possible, and make all the rounds.

Option 2 : Add an extra day to Littleton/Franconia. This region has so many great hikes and places to spot fall foliage. It’s well worth adding a day to this part of the trip if you have the extra time. This would allow you a half day to ride The Cog, and takes more scenic walks and hikes to enjoy the fall foliage.

Option 3 : Add an extra day to Vermont. On your extra day, you can take a day trip to Burlington and Shelburne, or spend the day driving the back roads .

Burlington & Shelburne, Vermont things to check out :

• First, the drive from both Stowe and Woodstock to Burlington on I-89 is beautiful in the fall. You’ll see lots of mountains ablaze with fall color.
• In Burlington, check out the waterfront area, and walk along Lake Champlain.
• Burlington also has an awesome craft brewery scene, and Foam Brewers is especially great.
• The American Flatbread restaurant in Burlington is a cozy place to stop for lunch.
• Church Street Marketplace in Burlington is a must!
• In Shelburne, you’ll want to spend most of your time walking around Shelburne Farms. This is a historic farm once owned by the Vanderbilt family, and has beautiful hiking trails, and you can also sample their homemade cheeses. Definitely do the Farm Trail, which takes you to an epic view of Lake Champlain.

Vermont back roads driving itinerary near Stowe :

This drive is easier to do from Stowe, but it’s also doable from Woodstock if you’re okay with a longer day. This itinerary is is order based on departing from Stowe, but you can also adjust based on which town you’re coming from 🙂

• The covered bridges in Montgomery, including Montgomery covered bridge (which is actually in Waterville), and Longley Covered Bridge.
• Barn Owl Bistro is a hidden gem nearby that’s a great little pitstop.
• The town of Cabot and the nearby AM Foster Covered Bridge are really beautiful areas to visit full of rustic Vermont charm.
• Peacham is a very small town with iconic landscapes and scenery.
• Bogie Farm in East Ryegate is a landscape that worthy of a postcard, and is especially beautiful in the fall.
• The drive between all these destinations will also be lovely and scenic, and packed with fall color.

1 Week (7 Day) New England Fall Road Trip Itinerary

If you have 7 days, welcome to your itinerary! This option is the same as the 10 day option, but eliminates Acadia National Park to save time.

7 Day Road Trip Overview

Day 1 : Arrival In Boston Day 2 : Drive To Jackson, NH + A Stop In Salem, MA Day 3 : Drive To Franconia Along The Kancamagus Highway Days 4-5 : Drive To Stowe or Woodstock, VT + Stay 2 Nights Day 6 : The Berkshires Day 7 : Return To Boston

For this itinerary, you can also eliminate The Berkshires, and stay an extra night in Jackson or Franconia.

5 Day New England Fall Road Trip Itinerary

With 5 days, you can go in a few different directions, and below, I break down my suggested options, and the benefits of each. This way, you can tailor it to your preferences.

Option 1 : Spend two nights in Boston with a day trip to Salem, then spend 3 nights in Stowe/Woodstock, VT.

Option 1 is perfect if you prefer staying in one place longer. This itinerary will allow you to stay in the same hotel in Boston for 2 nights, and take an easy day trip to Salem for the perfect fall day of Halloween fun and history! Then you can pick up your rental car (if you haven’t already), and drive to Stowe or Woodstock, VT for 3 days to explore both towns.

With 3 days in Vermont, you can easily see both Stowe and Woodstock, and maybe even plan a day of driving around the back roads. See the 12-day itinerary option for my suggestions on driving the back roads around Vermont during foliage season .

Option 2 : Spend 1 night in Boston, stop in Salem on your way to Franconia and spend 2 nights in Franconia. Then spend 2 nights in Stowe/Woodstock, VT, and then drive back to Boston.

Option 2 is perfect for those who still want to see as much as possible in 5 days. You’ll get to see a bit of New Hampshire and Vermont, while making a stop in Salem.

Note: For this itinerary, I would drive from Salem to Conway, and the drive The Kancamagus Highway on your way to Franconia so you get to experience the fall foliage along this route. But this itinerary option eliminates the stay in Jackson, as there are more fall things to do in Franconia.

Option 3 : Spend 1 night in Boston, 1 night in Salem, 3 nights in Stowe/Woodstock, VT, and then back to Boston.

Option 3 is perfect for those who really want to spend some time in Salem. This itinerary allows you to spend a whole night in Salem to really enjoy all the Halloween festivities and tours, and then you can spend 3 beautiful days in Vermont.

I excluded New Hampshire from this option because I felt like it would be too much to cram in when adding 1 night in Salem. But if you were feeling adventurous (I’ve been there, I get it! 😂), you can drive to Franconia, NH for 1 night after Salem, and then do 2 nights in Vermont instead of 3.

3 Day New England Fall Road Trip Itinerary

3 days in New England is the perfect long weekend getaway!

With 3 days, I suggest you stay in one location , and add day trips . If you’re flying into Boston, you can stay 1 night in Boston if needed, and then drive to Vermont or New Hampshire for 2 nights. If you’re not flying in, you can spend all 3 nights in Vermont or New Hampshire.

Stowe is very close to New Hampshire, and it’s only about 1.5 hours from Franconia. You can easily do a day trip from Stowe to New Hampshire, or vice versa, for this type of itinerary.

It would also be easy to work in a stop in Salem, MA, either on your way in or out of Boston.

Weekend New England Fall Road Trip Itinerary

For a weekend getaway in New England (essentially, 2 days), I would also recommend you stay in one place and take a day trip. For this itinerary, I almost always suggest Stowe or Woodstock. You can stay in either town, and spend 1 day exploring that town, and then the next day, exploring the other as a day trip.

Vermont Fall Road Trip Itinerary

Looking to just see Vermont? Excellent choice. It’s my personal favorite fall destination in New England (even though it’s a very close call 😉)

For a Vermont fall road trip , you can really do it in anywhere from 5-7 days. Of course, more is better to really see everything, but generally speaking, you can actually make it happen in a week or less. A popular route to take in Vermont is Route 100 , which runs the entire length of state, right through the middle. This allows you opportunities to veer off and see some other places as well.

For the purpose of this itinerary, I’m going to provide a week-long (7 day) itinerary, and you can adjust it to your own plans.

Day 1 : Bennington & Manchester Day 2 : Drive to Woodstock, stopping in Grafton and Weston on the way Day 3 : Spend the day in Woodstock Day 4 : Drive to Stowe, stopping in Montpelier if you’d like Day 5 : Spend the day in Stowe Day 6 : Staying in Stowe, take a day trip to Burlington & Shelburne Day 7 : Drive back

Day 1 Suggestions : Bennington and Manchester are pretty close to each other, so you can easily do both in one afternoon. There are some wonderful covered bridges in the area to see, and here are some more things to check out:

• The Bennington Battle Monument for fall foliage scenery.
• Downtown Bennington for shopping on Main Street (small, but cute!).
• Apple Barn is a few minutes from Main Street for a fun country store and bakery.
• Zoe’s in Manchester for lunch (great sandwiches!)
• Downtown Manchester for shopping in a cute town (don’t skip Northshire!)

Day 2 Suggestions : Grafton is a very small town, but it’s quintessential Vermont. It has a cute little cheese shop, and a nice little market/cafe called MKT Grafton, which is perfect for a quick bite. Also, swing by Weston to visit the Vermont Country Store.

For the rest of the itinerary, refer to the 10 day option for details 🙂

Click here to check out my post on a Vermont covered bridges road trip!

New Hampshire Fall Road Trip Itinerary

My second favorite fall foliage destination! Here’s my suggested itinerary for a New Hampshire-only fall road trip.

To just see New Hampshire , you can also spend anywhere from 4-7 days.

With 4 days, you can easily just stick to the White Mountains region, but I’m here to give you all my tips on even more awesome places to see in the fall season in New Hampshire ☺️ So, this itinerary will be 7 full days , but adjust as you need to!

Day 1 : Portsmouth Day 2 : Lake Winnipesaukee Days 3-4 : Littleton/Franconia Days 5-6 : North Conway/Jackson Day 7 : Drive back

Connecticut Fall Road Trip Itinerary Option

If you’ve seen all the “hot spots” around Vermont, New Hampshire, Massachusetts, and Maine, and you’re looking to explore a new part of New England in the fall, Connecticut should be next on your list!

As mentioned, my favorite place in Connecticut for fall foliage is the Litchfield Hills region. I always like to share that this region was what inspired Amy Sherman-Palladino’s creation of Stars Hollow, so Gilmore Girls fans will especially love this area.

The Litchfield Hills is very compact, and you can easily do a lot in a weekend here. However, 3-4 nights will allow you a nice, leisurely pace to explore all the amazing things this region has to offer in the fall.

The best towns to stay in in the Litchfield Hills region are:

• New Milford
• Washington/Washington Depot

Of all these towns, Litchfield probably has the most options when it comes to shopping and dining, however, they’re all very quaint and charming. I would pick whichever one has the best hotel for your plans.

If you have extra time for your Connecticut fall road trip, you can tack on places like Canaan to the north of the Litchfield Hills region, drive to Glastonbury, and then through the River Valley region, which includes the adorable towns of Chester and Essex. You can also choose to end your road trip in Mystic.

What To Pack For A New England Fall Road Trip

I always start every New England packing guide with the same thing, and this post is no different: begin to check the weather reports 5 days out from your trip to get an idea of what the weather will be like . And keep checking it until the day before you leave .

This is because weather in New England can change quickly, especially in the fall season. It’s not quite as dramatic as say … Iceland 😉 But, it can change and vary a bit. Generally speaking, fall will be chilly and a bit rainy. However, you could also have warm and sunny days. For longer trips, you’ll want to pack for both scenarios.

Here are some things I recommend you consider when packing for a fall road trip through New England:

Waterproof hiking boots . If you plan to do any hiking, or even nature walks, you’ll want a pair of sturdy boots that are waterproof. Even some attractions like Flume Gorge and other waterfalls in New Hampshire are pretty wet, so this is a good idea to stay dry and comfortable. I really like the Eddie Bauer K-6 Hiking boots. Find the women’s version here and the men’s version here . They’re a much less expensive version of the famous Danner hiking boots featured in the movie Wild !

Good hiking socks to keep your feet dry . An awesome brand to support is Tarn Tough Socks , which is a Vermont-based company. They’re an investment, but they’re also the best, and come with a lifetime guarantee!

Waterproof rain jacket to stay dry if it rains . You won’t want to let the rain slow you down, especially if there’s a lot in the forecast! So definitely pack one that’s completely water proof ( not water-resistant).

Layers . The best way to dress in the fall season is with layers. Under your rain gear, flannels, sweaters, and lightweight t-shirts (both short-sleeved or long-sleeved) work great.

Jeans . These work really well for most days. Fall in New England is pretty casual.

Hiking clothing . For any hikes you want to do, pack whatever clothes you typically wear and feel comfortable in 🙂

Comfortable sneakers or boots . When it’s not raining, a good pair of comfortable sneakers or cute boots work perfectly, depending on your plans. Since I drive from New York, I don’t usually have to worry too much about weight limits on a suitcase, so I’ll throw a pair of sneakers, flat boots/booties, and my hiking boots into the car. This is usually all I ever need.

Dinner outfits . New England is home to incredible places for farm-to-table dining, some of which are a bit more fancy. If you plan to go out for a nice dinner or two, you’ll want to pack accordingly. New England isn’t super fancy, so women can do a casual dress/jeans and a nice top with booties in the fall, and men can easily do dark-wash jeans and a button down top.

Reusable water bottle . You’ll need to stay hydrated while out exploring!

Day pack . If you plan to do any hiking, you’ll want to bring a day pack with you to carry your essentials. If you don’t plan to do any hikes, you can probably skip this, as you can keep most everything you need in your car or room.

Does It Snow In New England In The Fall?

Here’s the thing – it might if you’re up in the mountains. However, it doesn’t usually snow during peak foliage times. Usually, New England gets its first snow of the year later in October or early November. So, I wouldn’t worry about packing any snow gear or winter boots for your fall road trip.

How Do To A New England Fall Trip On A Budget

So, first thing’s first, you’ll unfortunately have to rethink what “budget” means in New England, especially during peak season in the fall. It’s generally more expensive than other areas of the country regardless of the reason, so during prime foliage times, prices will go up significantly.

Especially in the past, I never had the money to spend on several nights at hotels during this time of the year, so I have learned to do it on more of a budget. Not necessarily cheap, but not as tough on the wallet 😉 Here are my tips:

• Stay in motels. I love a good hotel splurge, and do it more now than I did in my 20s and early 30s. But for most of my road trips when the focus in exploring outdoors, I stay in motels with efficiency kitchens . You can find some really nice ones, and while they’re likely to be outdated, they’re usually clean and cozy.
• Efficiency kitchens allow you to make some meals at home. For a road trip style trip, this may be more challenging, as it’s hard to bring perishable items with you to store in a fridge. But I usually try to make my own breakfasts to save money, and pack snacks to have for lunch.
• Stay outside of town. If you’re really on a tight budget, you can stay outside of the towns you’re visiting. Places like Franconia, Stowe, and Woodstock charge premium rates for peak season, so you’re likely to find deals a town or two away.
• Go camping! If you’re really adventurous, you can go camping! There are camp sites all over New England, and this will definitely be more affordable. One thing to keep in mind is the colder weather, and for this reason, some camp sites may close down after Indigenous People’s weekend in October. But many remain open, and offer Yurt-style camping, too.

Is Fall In New England Worth It?

A resounding yes! I truly believe this is such a magical time to visit – if not the most magical time. Despite the crowds and the cost, it’s more than worth it. Many of the landscapes you’ll see are actual stock photos and postcards, and since so many people equate the fall season to all things cozy, there’s really no cozier place to be than in New England during foliage season.

More posts you may enjoy:

• Fall In New England: The Best Things To See & Do
• Vermont In The Fall: Festive Things To Do!
• Fall In New Hampshire: The Best Things To Do
• Fall In Massachusetts Ultimate Guide: All The Best Things To Do & Foliage Spots!
• The Best 7 Day New England Road Trip Itinerary For Any Season
• Best Stops To Make On A Boston To Stowe, VT Road Trip
• Vermont vs. New Hampshire In The Fall
• Maine In October: Best Towns For Foliage & Things To Do!
• Best Vermont Pumpkin Patches & Farm Stands To Visit In The Fall
• Awesome Corn Mazes In Vermont
• Best Time To Visit New England
• Best Time To Visit Vermont

That’s A Wrap On The Best New England Fall Road Trip Itinerary

And there you have it! All my tips and expert advice on planning the most epic New England fall road trip during foliage season! This truly is such a wonderful, once-in-a-lifetime experience that everyone should do at least once, and hopefully, you’re now well on your way to planning your own foliage adventure through New England!

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Road-Tripping New England: My Suggested Itinerary

I’ve said it before and I’ll say it again: The United States is made for road trips . With its bustling cities, rugged national parks, and delicious eats, the sheer size and diversity of this country never cease to amaze me.

I’ve road-tripped the USA five times, spending a cumulative year exploring its cities, towns, and parks. To me, a road trip is the best way to explore the US. By driving the back roads and getting out of the cities, you really get to see the diversity and natural beauty of the country.

One region in particular that I love to drive around is New England.

Having grown up in Boston and gone to college in Western Massachusetts, I’ve spent a lot of my life in this part of the country. I’ve also road tripped around the region.

During a recent summer, I explored parts of Maine , Cape Cod, and upstate New York that I had never seen before.

And yeah, I’m biased because I grew up here, but I really do think New England is one of the most special areas of the country. It offers delicious seafood, friendly and welcoming people, incredible natural beauty, charm, and plenty of history.

If you’re thinking of visiting, here’s a suggested road trip around New England to help you get a feel for the region:

Table of Contents

Days 1-3: Boston, MA

Days 4-5: portland, me, days 6-8: bar harbor, me, day 9: bangor, me, days 10-12: moosehead lake, me, days 13-14: mount washington, nh, days 15-17: burlington, vt, days 18-19: green mountain national forest, vt, days 20-22: the berkshires, ma, day 23: amherst, ma, day 24: back to boston, bonus destination: cape cod, ma.

These are some of my favorite things to do in Boston:

• Walk the Freedom Trail – This 2.5-mile (4km) route takes you through colonial Boston. Starting in the Boston Common and winding past Faneuil Hall, the Old State House, and Bunker Hill, this historical walk teaches you about life in colonial and revolutionary times. If you’d prefer a guided tour, Boston History Company runs daily tours for $31 USD that offer excellent insight into the area’s important past.
• See the Museum of Fine Arts – This museum has over 450,000 pieces of fine art, from the pre-Columbian era to Italian Impressionism. It’s one of the best collections in the country. Admission is $27 USD.
• Visit Bunker Hill Monument – The Battle of Bunker Hill in 1775 was one of the first major clashes of the Revolutionary War. While the redcoats won, the Americans wore British forces down more than was expected. The monument stands 221 feet tall; you can climb to the top to enjoy the view (it’s the best view of Boston).
• Lounge in Boston Common – This is the oldest city park in the US, dating to 1634. It was once used as communal pasture land by Puritan settlers (they also executed some “witches” here as well). Today, it’s a great place to relax, people-watch, and picnic.
• Visit Harvard – Harvard University is the first and oldest university in the country (founded in 1636, far predating the United States). The campus offers free one-hour tours through the grounds and buildings. Afterward, grab a coffee and people-watch in the alternative and artsy Harvard Square.
• Catch a game at Fenway Park – This is one of the oldest baseball parks in the country (it opened in 1912). Bostonians are die-hard Sox fans, so even if you don’t like baseball, go for the cultural experience. Tickets start around $29 USD for standing room or bleacher seats, and $39 USD for the grandstand. Guided tours of the stadium are offered year-round as well. There are various tour options, but the standard guided tour lasts 90 minutes and costs $25 USD per person.

For more suggestions on what to do in the city (and there’s plenty), check out my free guide to Boston .

Where to Stay

• HI Boston – This is my favorite hostel in the city. It’s clean, spacious, and social, and the staff are super friendly and helpful.

For more suggestions, here is my list of the best places to stay in Boston .  

• Visit Peaks Island – This small island is home to around a thousand people. Located just 20 minutes off the coast, it’s a laid-back place to eat, lounge, and check out the quaint shops. There’s also a small World War II museum here, as well as a neat umbrella cover museum (it’s more interesting than it sounds!).
• Try a Holy Donut – Holy Donuts are made from Maine potatoes (which sounds weird, but they are incredibly tasty), so they are at least somewhat healthier than your standard donut. There’s always a line, so try to get there early!
• See the lighthouses – There are several historic lighthouses worth seeing nearby, including the Portland Breakwater (which was designed to look like a Greek monument), Spring Point Ledge (which was built in 1897 and is open for tours on weekends), and Portland Head Light (which was built in 1791).
• Wander Victoria Mansion – This ornate mansion-turned-museum, built in 1860 and declared a National Historic Landmark in 1971, boasts a brownstone exterior and elaborate interior furnishings. It’s incredibly lavish, shedding light on what life was like for the well-to-do in the late 19th century. Admission is $19.25 USD.

While you’re in Portland, be sure to check out some of the city’s best restaurants, including Duckfat (get the fries), Eventide Oyster Co. (best oysters in the city), and Bite into Maine (best lobster roll in the city). For drinks, head to Rising Tide Brewery.

• Black Elephant Hostel – This hostel has a cool, colorful interior and social atmosphere, and is perfectly located near lots of restaurants and shopping.

Moreover, on the way up from Portland, take Route 1 and stop for food along the way in any one of the numerous historic fishing towns. If you like oysters, stop at Glidden Point Oyster Farm.

Here are some things to see and do in and near Bar Harbor:

• Explore Acadia National Park – This gorgeous national park encompasses forests, lakes, and mountains, and covers a large swath of the Atlantic coastline. It’s incredibly popular in the summer for hiking, biking, camping, kayaking, and more. You could easily spend a couple of days just exploring the park. A 7-day vehicle pass is $35 USD and camping starts at $22 USD per night.
• Visit Abbe Museum – This museum showcases the area’s indigenous history and culture. It’s very informative and sheds important light on a history often overlooked. It’s part of the Smithsonian, so you know it’s going to be good! Admission is $10 USD.

Like the rest of Maine, Bar Harbor has some wonderful places to eat. My favorites were the Travelin Lobster (best lobster roll in the area), Havana (upscale dining), and Rosalie’s (delicious food all around).

• Bar Harbor Manor – This is a cozy hotel right outside Acadia National Park with lots of outdoor space to relax in, free Wi-Fi, and an indoor parlor with a fireplace.

My favorite places to eat are Fiddleheads (delicious food all around) and Judy’s (best diner breakfast). For a drink, head to Mason’s Brewing.

Where to Stay Bangor is a small town, so you’ll want to compare prices on Booking.com and Airbnb to see what best suits your budget.  

Spend a couple of days here relaxing away from the crowds, hiking the plethora of trails, spotting moose, or taking part in all the lake activities on offer.

For dinner or drinks, head to the Stress Free Moose Pub in Greenville.

• Leisure Life – This accommodation is basic, but it’s in a great location (in Greenville), and the staff are super helpful.

Some of the best day hikes up the mountain are Tuckerman Ravine Trail (4.2 miles, strenuous), Lion’s Head Trail (4.2 miles, strenuous), and Jewell Trail (5.2 miles, moderate).

Where to Stay You can stay in nearby Gorham or Littleton. Check Booking.com and Airbnb to see what best suits your budget.  

Some of my favorite things to do here are the following:

• Wander Church Street – This pedestrian-only thoroughfare is the heart of the city. Café-hop, browse the bookstores and other shops, and take in the slow pace of life.
• Get out on the water – Spend some time out on the water and soak up the sun. Boat rentals, cruises, paddle boarding, kayaking — you can do it all here. There are also several beaches you can lounge on, with North Beach being the most popular.
• Visit Ben & Jerry’s – This is where the global ice cream brand originated. If you have more time, you can visit the nearby factory in Waterbury and see the “ice cream graveyard,” where Ben & Jerry’s commemorates its obsolete flavors.
• Indulge in craft beer – Burlington is a craft beer mecca, home to over a dozen breweries. Go bar- or brewery-hopping to taste the best the city has to offer. Local favorites include Foam Brewers, Zero Gravity, Fiddlehead Brewing Company, and the Burlington Beer Company.

Where to Stay There are no hostels here, so compare prices on Booking.com and Airbnb to see what best suits your budget.  

Highlights include Thundering Falls (a 140-foot waterfall), the Long Trail (a 272-mile hike and the oldest long-distance trail in the country), and the panoramic view from the 4,000-foot Camel Hump summit.

Since it’s a national forest, camping here is free (unless signs advise otherwise).  

Here are some things to see and do:

• Hike Mount Greylock – Standing 3,491 feet tall and located in a state park encompassing over 12,000 acres, Mount Greylock is the highest peak in Massachusetts. There are several trails that lead to the summit (including a portion of the Appalachian Trail). The hike takes around 90 minutes, and the views from the top are absolutely breathtaking — you can see for miles!
• Visit the Norman Rockwell Museum – Norman Rockwell, the prolific American painter and illustrator, spent much of his life in Stockbridge. A museum was established there to showcase his life and works, highlighting the evolution and impact of his art. Admission is $20 USD.
• Explore Natural Bridge State Park – Located in North Adams, this park is home to a natural bridge of white marble (which is over 550 million years old) as well as an old marble quarry. There’s an easy trail around the bridge and quarry, and plenty of relaxing fields and meadows to picnic in. Parking is $20 USD for out-of-state residents.

Be sure to tour the Emily Dickinson Museum, which commemorates the poet (she was born in Amherst in 1830). The house where she was born and grew up, now converted into a museum, includes artwork, artifacts, clothing, and poetry from Dickinson’s life. There are often events and poetry readings here, so check the website to see what’s on during your visit. Guided tours last 60 minutes and cost $16 USD.

As for food, Antonio’s Pizza is a must (they have some really inventive toppings). I ate a lot of it during college! I’m also a big fan of Black Sheep for sandwiches and House of Teriyaki for Japanese food.

It’s just a short two-hour drive back to Boston, so feel free to stop along the way to stretch your legs. There are plenty of places to stop along the way or just do more things in Boston!  

Here are some things to see and do during your stay:

• Go whale watching – From April to October, you can see finback, minke, and humpback whales, as well as dolphins and seals. Tours cost around $67 USD.
• Hike or bike the National Seashore – Created in 1961 by JFK, this park spans over 43,000 acres. There are 11 hiking trails, as well as half a dozen cycling trials. All of them are well marked so it’s an easy way to stretch your legs and take in the beautiful landscape.
• Visit some lighthouses – There are dozens of picturesque lighthouses around Cape Cod, some of which are open to the public. Don’t miss Nauset, Nobska, and Highland lighthouses.

New England is one of the most beautiful parts of the United States. Its size makes it perfect for road trips, offering a nice mix of cities, small towns, and stunning natural beauty. It also has some of the best seafood in the country, lots of hiking and biking opportunities, and some of the friendliest people in the country. I’m proud to have grown up in this region and encourage you to explore my backyard!

Book Your Trip to the United States: Logistical Tips and Tricks

Book Your Flight Use Skyscanner to find a cheap flight. They are my favorite search engine because they search websites and airlines around the globe, so you always know no stone is being left unturned.

Book Your Accommodation You can book your hostel with Hostelworld as it has the biggest inventory and best deals. If you want to stay somewhere other than a hostel, use Booking.com as it consistently returns the cheapest rates for guesthouses and hotels.

Don’t Forget Travel Insurance Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it, as I’ve had to use it many times in the past. My favorite companies that offer the best service and value are:

• Safety Wing (best for everyone)
• Insure My Trip (for those 70 and over)
• Medjet (for additional evacuation coverage)

Looking for the Best Companies to Save Money With? Check out my resource page for the best companies to use when you travel. I list all the ones I use to save money when I’m on the road, and I’m sure they will do the same for you.

Need an Affordable RV for Your Road Trip? RVshare lets you rent RVs from private individuals all around the country, saving you tons of money in the process. It’s like Airbnb for RVs.

Want More Information on the United States? Be sure to visit our robust destination guide on the USA for even more planning tips!

Got a comment on this article? Join the conversation on Facebook , Instagram , or Twitter and share your thoughts!

Disclosure: Please note that some of the links above may be affiliate links, and at no additional cost to you, I earn a commission if you make a purchase. I recommend only products and companies I use and the income goes to keeping the site community supported and ad free.

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Home » North America » USA » New England

EPIC New England Road Trip Itineraries (2024)

Going on a New England road trip  has to be one of the best ways to experience the region! With your own vehicle, you’ll be able to go wherever you want, stay where you like, and see whatever you fancy.

New England has been charming visitors for a long time. Of all of the regions in the USA, New England has some the richest history (being the birthplace of the nation and all), some of the most exciting locals, and best seafood, period.

And the fall foliage in New England? What more can be said about this phenomenon that hasn’t be said by dozens of movies – it’s simply one of the most romantic sights in the USA.

New England is by no means cheap nor easy to travel without some guidance. In order to see the best of New England, and not drop a fortune while doing so, you’re going to need a little assistance.

Don’t worry – we have the insider information you need for an EPIC journey. So what are we waiting for?! Let’s get the ball rolling on your New England road trip itinerary!

Best Time of Year to Road Trip New England

Best new england road trip itineraries, places to visit in new england, off the beaten path new england road trip ideas, new england road trips costs, final thoughts about new england road trips.

With something always going on, a road trip to New England is possible at any time of the year! In New England, summers are for beach trips, fall is for the foliage, winter is for skiing, and spring is for festivals.

If you can stand the occasional poor weather – the blinding snow and sometimes uncomfortable humidity – then you’ll do just fine in New England.

The climate in New England isn’t always agreeable, a fact that many residents will remind you of when you’re there. Winters are long and can be bitter cold and summers feel unfairly humid and short.

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 .

The weather in New England has a habit of being bipolar as well, appearing beautiful one moment only to turn to shit in a moment.

This doesn’t stop New Englanders from having a good time though as they seem to have something to do 365 days of the year. They take the weather with a grain of salt, as they should, and simply say, “if the weather’s no good, just wait 15 minutes (and it’ll be better).”

Outside of the mountainous regions, which can have Arctic qualities, there are no huge climatic swings in New England. Overall, temperatures are relatively cool and precipitation is spread throughout the year.

What makes New England feel so cold is the Canadian winds that come down and wreak havoc. These winds penetrate to the bone and can really ruin your day.

A thermometer may read 30 Fahrenheit but with the wind chill, it could feel like 0. Be sure to bring lots of layers and a windbreaker in the winter.

Fall in New England means changing foliage, the astounding beauty of which attracts every Joe Schmoe and his family to visit. If you’re on a road trip during this time, expect much higher prices and much less availability. Having said that, it’s one of the best places in the world to visit in September and October, so it’s worth it!

Get 15% OFF when you book through our link — and support the site you love so dearly 😉

Booking.com is quickly becoming our go-to for accommodation. From cheap hostels to stylish homestays and nice hotels, they’ve got it all!

Below is a list of sample New England road trip routes, from East Coast budget adventures to more comprehensive trips that cost a bit more. Varying from 4 to 14 days in length, they cover many of the top destinations in New England. Each itinerary provides day-by-day highlights, which are meant to give you some good New England 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. 😉

4-Day New England Road Trip Itinerary: Boston and the Cape

4 Days: Boston and the Cape

Arrive in Boston via Logan International Airport or by other means. Once you’re checked into your lodge and settled in, get ready to see the town!

Our  Boston itinerary  includes a visit to downtown Boston to see:

• Fenway Park
• The Freedom Trail
• Acorn Street
• Trinity Church
• Boston Commons

After that, head to bed because the next day we start again!

Today you’ll be getting off the beaten path in Boston.

• Southend for an authentic Bostonian experience
• Cambridge for Harvard and MIT
• East Boston for good food and views
• Walden Pond for transcendental fans
• Bunker Hill for history

Today we’re officially starting the drive, so have your car organized for a road trip to Cape Cod. Start driving on Highway 6 and then transfer to Highway 3 prior to the Cape Cod Canal. Once you’ve arrived, find your Cape Cod lodge/campsite and get set up.

Next, we’ll explore the Cape. Activities include:

• Lighthouses
• Charming settlements
• Trinket shopping
• Historical landmarks
• Biking and hiking
• Cape Cod Rail Trail

This is the last day of your short road trip from Boston. You can opt for a few different choices today.

Either consider visiting Nantucket Island or Martha’s Vineyard via the ferry. If not though, you can continue exploring the island and seeing what’s around.

When all is said and done, pack your things for a late flight in the evening or a flight the next day.

7 Day New England Road Trip Itinerary: New England’s Best Fall Foliage

7 Days: New England’s Best Fall Foliage

• Arrive at Logan International and organize your car; skip this if you’re coming by road from elsewhere.
• Hit the road immediately and head west on the I-90 and I-84 for Hartford, CT.
• Pass Hartford and continue onto the Litchfield Hills in West Connecticut.
• Spend the night in Kent, Cromwell or elsewhere.
• Admire the foliage.
• Depart from your lodge and head north on I-7 through the Housatonic Valley; red and gold foliage in abundance.
• Arrive at the junction between I-7 and Highway 2 near Williamstown.
• Highway 2 is colloquially referred to the Mohawk Trail, which offers some of the best of New England as well as excellent fall colors.
• Stay nearby and drive along the 2 to your heart’s desire.
• Drive on the Mohawk Trail if you haven’t already.
• When ready, head for Green Mountain National Forest of Vermont via I-7 again.
• Drive through the Green Mountains until Burlington.
• Grab a beer and chill for the night.

Today is a long but rewarding day.

• Depart from Burlington and head for Cambridge, VT.
• Hit the 108 and Smuggler’s Notch for excellent mountain views and foliage.
• Make your way east towards Bath, New Hampshire.
• Turn onto Highway 112 before Bath, which is the beginning of the Kancamagus Highway.
• Continue onto Lincoln, admiring the scenery along the way.
• Find a Lincoln Airbnb or stay in North Conway or elsewhere in the White Mountains.
• Finish the Kancamagus Highway (112), which terminates at Conway.
• Head north upon reaching Conway on Highway 16.
• Enjoy Mt Washington and White Mountain National Forest, which is particularly fantastic in fall.
• Turn onto I-2 and then again onto 113 to reach Evans Notch.
• Finish up and head south towards Portland for the night.
• Drive to Acadia National Park , which is one of the best places for fall foliage in New England.
• Make a tour around Mt Desert Island and get a full dose of autumn splendor and coastline.
• Spend the night around Acadia or back in Portland.
• Consider spending the night in Camden as there is excellent foliage here.
• Pack up and head back to Boston.
• Spend the day exploring the city.
• Get ready to depart that evening or the next day.

14-Day New England Road Trip Itinerary: Ultimate New England

14 Days: Ultimate New England Road Trip

Follow the first East Coast itinerary listed here  except  instead of returning to Boston at the end of day 4, relax and stay the night in Cape Cod. We’ll be moving on from there the next day…

• Depart from Cape Cod and hit I-6, which will take you all the way to Providence, Rhode Island.
• Explore the city and its architecture.
• Be sure to drop by one of the many breweries and brewpubs.
• Spend the night in or around Providence.
• Wake up and head directly for Newport via Highway 114.
• Spend the day exploring the opulent town.
• Be sure to visit the many mansions and estates as well as Fort Adams in the south.
• Depart when you’re ready.
• Drop by Narragansett for some beach time if you have time.
• Stop in Old Saybrook for the night or continue onto New Haven.
• Depart from your lodge and make your way north.
• Head to the state capital Hartford.
• Wadsworth Falls
• Buttermilk Falls
• Settle in Hartford for some culture and good partying or…
• Head to Litchfield Hills for a quieter night.
• Make your way up Knowledge Corridor or Housatonic Valley towards Vermont.
• Be sure to drop by the Mohawk Trail in Northwest Massachusetts for some scenery and history.
• Hit highway 7 and make the long drive to Burlington.
• Reward your hard work today with a beer.
• Spend the day exploring the Green Mountains of Vermont.
• Climbing the  Camel’s Hump .
• Hiking around  Mt Mansfield .
• Check out  Smuggler’s Notch .
• Rafting on the  Mad River .
• Spend the night in Burlington again.
• Depart from Burlington and head east towards Lincoln, New Hampshire via I-89.
• Arrive in the White Mountains and settle into whatever lodge/campground you have booked.
• Spend the remainder of the day in the mountains.
• Flume Gorge
• Mt Washington
• Franconia Notch
• Arethusa Falls
• Lonesome Lake
• If you arrived early enough, considering overnighting in a backcountry campsite.
• Wake up and knock off any remaining activities.
• Consider doing the full-day Presidential Traverse but, full-warning, it’s quite arduous.
• Lay your head down for the night, preferably around a campfire with a drink.
• Depart from the White Mountains and travel on Highway 302 to Portland, Maine.
• If you stay in Portland, visit the many maritime landmarks, trinket shops, and breweries.
• Spend the day exploring Acadia National Park.
• Taking a road trip around  Mt Desert Island .
• Climbing  Cadillac Mountain .
• Visiting  Jordan Pond .
• Relaxing on  Sand Beach .
• Walking around  Bar Harbor .
• Head to your lodge for the night.

Below is a list of the best road trip destinations in New England. Study them well and decide which ones you like the most.

Road Trip to Boston

Boston is the largest city in New England and, honestly, one of the coolest cities in the entire United States. With gorgeous architecture, some of America’s most important history, and hugely diverse demographics, there’s little chance you’ll run out of things to do in Boston .

Downtown Boston – the area with all the skyscrapers – is where you’ll find the majority of the city’s attractions. Notable points of interest in Boston Downtown include Fenway Park , the Trinity Church, Boston Commons, Acorn Hill , and the North End. You could easily hit all of these places in a few hours by walking.

North across the Charles River is Cambridge , home to the famously exclusive Harvard College and MIT . Both campuses are worth visiting – the former for traditional architecture and the latter for ultra-modern. The whole of Cambridge is pretty affluent, being inhabited by students and leaders in tech, but thankfully doesn’t suffer from too much snootiness.

South Boston is the home of the “southies” aka those people that sound like Matt Damon from Good Will Hunting . Aside from the impressive JFK Library, there isn’t a whole lot to do here besides people watch, which is, admittedly, awesome.

Finally, across the Boston Channel and next to Logan International is East Boston, which is where most of the immigrants live. These means this is one of the best places in Boston to grab food! The views ain’t bad either.

While you’re travelling around Boston , be sure to also get outside of the city of as well! The historical city of Concord , as well as the hallowed Walden Pond , are both worth a day trip.

Road Trip to Cape Cod and the Islands

Cape Cod is a large, prominent peninsula located south of Boston. It is an immensely popular getaway destination due in part to its extensive coastline and profuseness of quaint coastal towns.

Combined with the ever-enchanting Martha’s Vineyard and Nantucket Island , both located nearby, and you have an assembly of some of the best of New England.

Cape Cod is a very large region, surprisingly so, and is broken into several districts. Because of its size, history, and prosperity, Cape Codians are very proud of their home and consider it more than just a tourist destination. There are loads of great places to stay in Cape Cod , if you fancy extending your trip!

There are several charming towns on Cape Cod that are worth visiting. Hyannis is most notable for the Kennedy Compound , which served as the holiday home for JFK and his family, as well the enormous Beech Tree on Main Street .

Fans of Kurt Vonnegut may also be interested in nearby Barnstable as it was his home for several decades. Affluent Chatham has one of the best lighthouses and local baseball teams on the Cape (Cape Codians are crazy for the sport).

Finally, Provincetown is famous for its artsy and expressive LGBT community.

Most everyone comes to Cape Cod to play in the sea as the peninsula has some of the best beaches in New England. Make no mistake, there are a lot of them too.

Stunning stretches of sand can be found at Nauset Beach, Lighthouse Beach, Sandy Neck Beach, Mayflower Beach, and pretty anywhere else along the Cape Cod National Shoreline Park . You may get lucky and even see a migrating humpback whale!

No road trip to Cape Cod is complete without a trip to Nantucket Island or Martha’s Vineyard – both are among the most desirable places to visit in New England, during summer especially so.

Martha’s Vineyard is full of grand residences for the rich as well as picturesque beaches. Nantucket is similar to Martha’s Vineyard but smaller and quieter. You can catch a ferry to either at Hyannis.

Road Trip to Rhode Island

Rhode Island has a little bit of everything. The largest city, Providence , is often considered a good alternative to Boston, and the surrounding state offers quintessential scenery including rugged coastline, quaint townships, and, of course, the fall foliage New England is so beloved for.

Providence is the third largest city in New England. For a long time, Providence had a bad reputation for being sketchy, crime-ridden, and corrupt but, following massive economic pushes, is currently undergoing an urban renaissance. It’s now a very appealing city thanks to its history with a bustling college scene, solid nightlife, and heaps of stuff to do .

Providence is a small city so getting around on a foot is a very reasonable task. Walk around and take note of the diverse architecture. Be sure to see the State House, the eclectic Brown University, the restored Arcade, and the First Baptist Church , among others, for a lesson in American architectural history.

For a languid afternoon, try visiting one of the many museums and/or parks in Providence. Certain neighborhoods, like Federal Hill, College Hill, and Downcity all offer nice urban panoramas as well. End your day at one of the many breweries in the city.

Rhode Island’s other noteworthy city is Newport . An opulent town, full of mansions and elegant avenues, Newport is a prime example of New England decadence. Rosecliff estate served as a setting in the recent Great Gatsby film and its neighbors – The Beakers and Marble House – are equally grandiose.

There is a thriving art scene in Newport and jazz, in particular, is praised here. There is an awesome jazz festival at Fort Adams. Festival or not, Fort Adams is worth seeing because it is one of the most important historical structures in New England.

Newport has many beautiful city beaches including Bailey’s, Easton, and Gooseberry. To see some real contenders for “best beaches in New England,” head across the Jamestown Verrazano Bridge to Narragansett . If you’re ever wondering where to stay in Newport, you should definitely consider staying in one of the more historic bed and breakfasts in Rhode Island there.

Coastal Connecticut Road Trip

Connecticut is an eclectic state visited often by both New Englanders and New Yorkers, the latter of which only live a short train ride away. It is a popular getaway for city folk who need a break from the grind and some time in rural New England.

With a lovely coastline, romantic countryside, and a number of dynamic cities, Connecticut is a great stop along any New England road trip route USA.

Connecticut can be broken down roughly into three parts: the coast, the “Knowledge Corridor,” and the countryside. This section will cover coastal Connecticut , which is a part of Southern New England.

Driving west along Highway 95 from Rhode Island, you’ll pass by some of the most beautiful beach towns in New England. Stonington is a good place to learn about the maritime history of the state – particularly at the Old Lighthouse Museum .

Old Saybrook is one of the prettiest coastal towns in Connecticut and is also a stone’s throw away from Gillette Castle . On the way to New Haven is Hammonasset Beach , which is the longest and busiest beach in the state. Make sure to stay in one of the stunning cabins in Connecticut to make the most out of all this natural scenery.

New Haven marks the beginning of a long stretch of urban development that spans all the way to New York state.

New Haven is most famous for Yale University , which is arguably the top attraction in the city. Being a college town, New Haven has a great art scene and nightlife. The pizza is also particularly good in this town.

As we continue further west along 95, we’ll pass by many more beautiful New England towns. There’s quiet Milford , which has a great beach called Silver Sands .

Next, you’ll pass through industrial Bridgeport . After that is upscale Stamford , glorified dockyard for millionaires from New York (there are some good beaches as well).

Finally, you’ll end up in Greenwich , which is one of the most admired towns in New England, due in part to its beauty and close proximity to New York.

There are a ton of awesome B&Bs in Connecticut where you can stay in a historical building and enjoy that welcoming East Coast hospitality.

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Road Trip through Connecticut and Massachusetts

The interior of Connecticut is dominated by the Knowledge Corridor , which hosts one of the densest collections of higher learning institutions, not to mention one of the largest populations in New England.

Travel outside this packed area and you’ll find some of some of the best of New England pastoralism including traditional townships, rolling hills, and a distinctive tranquility. Visiting either on a New England road trip provides excellent insight into the region.

Let’s start with the quieter section – the western part of Connecticut referred to as the Litchfield Hills. This part of the state is very rural with few inhabitants and even fewer visitors.

There are a number of beautiful New England towns here, including Kent , Cornwall , and New Milford , as well some lovely natural attractions like Kent Falls, Burr Pond, Candlewood Lake, and Mohawk Mountain . These are also some of the best places to visit in New England in the fall.

Moving along to our main destination, we first make for Hartford , Connecticut’s state capital and the beginning of the Knowledge Corridor. Hartford is considered one of the great culture capitals of the region.

There are several libraries and art collections dedicated to various historical figures, including Mark Twain, spread throughout the city. Reportedly, West Hartford also has a fairly active nightlife.

Outside of Hartford are a number of parks worth visiting. Examples include Enders State Forest/Falls, Buttermilk Falls , and Wadsworth Falls .

We continue our New England road trip north on Highway 91 through the Connecticut River Valley. This is the heart of the Knowledge Corridor, a title that refers to the huge concentration of colleges and universities in the area. This corridor runs all the way into Massachusetts and terminates in Springfield.

Springfield is a great city full of Victorian architecture and some of the coolest museums in New England. Be sure to visit the NBA Hall of Fame , if you’re interested in sports, as well as the Dr. Seuss Sculpture Museum , if you had a childhood.

Vermont Road Trip

True to its nickname, Vermont aka The Green Mountain State is a wild wonderland and a favorite playground for New England outdoors people. With some awesome skiing and hiking in addition to several fall foliage drives, which are among the best in New England, Vermont is a great escape from the more developed CT, MA, and RI. Here is the best opportunity to stay in a cabin in Vermont for a truly off-the-grid experience.

Starting in the south of Vermont, you’ll first arrive at the mountains from which the state gets its name, the Green Mountains . A subrange of the Appalachia, the Green Mountains are home to the state’s highest peaks as well as the best mountain activities.

Some of the best ski resorts in Vermont are Sugarbush, Stowe Mountain, Killington, Mount Snow , and Jay Peak. Though the slopes aren’t as epic as say those in Colorado or Oregon, they still get dumped on with snow and have decent runs.

If skiing isn’t your bag, why not try portions of the Green Mountain Long Trail ? This extension of the Appalachian Trail is noteworthy for hitting all the range’s highest peaks but is, for this reason, difficult at times.

Casual hikers and campers can also take advantage of the many free backcountry campsites and quaint bed and breakfasts in Vermont .

Other natural attractions worth visiting in Vermont are the Mad River, Quechee Gorge, Camel’s Hump , and the many gorgeous lakes – most notably Lake Willoughby and Lake Champlain.

Montpellier is the state capital of Vermont though Burlington is the largest and most exciting in the state.

Burlington is famous for being a hippy town as well as drop dead gorgeous because it lies on the banks of Lake Champlain. Burlington makes for an excellent base for exploring Vermont’s outdoor spaces with many quality bike paths for cycling enthusiasts.

Like any good liberal college town, Burlington has plenty of bars, and the breweries, in particular, are excellent. You ca check out Airbnbs in Vermont for cozy and comfortable stays.

Road Trip to New Hampshire

New Hampshire is very similar to Vermont in that it’s mostly visited for its epic settings and free-spirited culture. With the highest peak in all of New England, Mount Washington , as well as the beautiful White Mountains , New Hampshire is another great New England road trip destination for adventurous travelers.

If you’re on a summer New England road trip, then you’ll obviously want to hit the trails in New Hampshire. This state has some of the best hikes in New England in addition to some decent summits.

As previously mentioned, Mt Washington is the highest peak in New England and can be summitted in a day either by foot or by cog train (that’s cheating though). Be mindful of foul weather.

New Hampshire’s Mt Monadnock is argued to be the second most climbed peak in the world next to Mt Fuji, but many don’t count Monadnock because it has no glacier. (Mt Hood in Oregon is the second most climbed glaciated peak in the world.)

Another rewarding and arduous hike is the Presidential Traverse where you navigate across 11 of the state’s highest peaks. Also consider visiting Lake Winnipesaukee , Franconia Notch, Arethusa Falls, Lonesome Lake , and the Flume Gorge .

Those on a winter or spring New England road trip will be happy to hear the skiing is also quite good in New Hampshire. Popular ski resorts include Loon Mountain, Bretton Woods, Cannon Mountain , and Waterville Valley .

New Hampshire is pretty sparsely populated and there aren’t too many bustling urban centers here. There are a couple of little towns worth stopping in still.

Hanover is home to the famous Dartmouth University and is gorgeous in its own right. Jackson is a gorgeous place to stay in the White Mountains and makes for a great base. Finally, Portsmouth is one of the most historically significant towns in New England and, more importantly, has great breweries.

Road Trip on the Maine Coast

Maine will be a highlight for any New England Coast road trip! With epic seascapes and even more epic seafood, Maine has a lot to offer.

Many people have fallen in love with Maine’s coastline, too many perhaps. Coastal Maine isn’t exactly hidden these days and so anyone on a summer road trip in New England will have to deal with large crowds.

You can definitely get off the beaten path in Maine but that is a topic that we will be discussing in the next section .

Driving from Portsmouth, NH, you’ll head north on the 95 to Portland , Maine, catching glimpses of the shoreline along the way. You’ll pass by several of Maine’s best beaches and towns including York, Ogunquit, Cape Elizabeth , and Goose Rocks . Upon arriving in Portland, you may think that it’s a small coastal town but is, in fact, the largest “city” in the state.

Portland is one of the best places in New England, ridiculously charming and full of quaint little attractions. You’ll learn a lot about its maritime history at the Old Port and also be afforded the opportunity to shop for artisanal souvenirs. The seafood is obviously excellent in Portland and the beer is especially delicious if not abundant.

Moving on from Portland, we continue our New England coast road trip deeper into the state. Driving on the 1 you’ll have lots of opportunities to visit the coast. Boothbay is an elegant destination, Camden is gorgeous, and Popham Beach is arguably one of the best beaches in New England.

Our ultimate destination is Acadia National Park , the only national park in New England. It is a superlative place with some astounding scenery, not to mention some of the best hikes in New England.

Spend the night in the charming seaside town of Bar Harbour , where you’ll get to try Maine’s famous cold lobster roll. You’ll find some epic Maine B&Bs here run by friendly locals.

Then go for a drive around Mt Desert Island , the island on which Acadia is located, and then explore local sites like Jordan Pond and Sand Beach . Note that you’ll have to pay an entry fee for Acadia.

Below is an overview of the Great North Woods of New England, arguably the wildest place in the Northeast. Those with the will and proper transport will be rewarded with virgin woods, pristine rivers, and an abundance of local wildlife.

Great North Woods

The Great North Woods is one of the quietest, most underdeveloped, and most beautiful places in New England. It refers to the extremely wild and untouched woodlands of northern New Hampshire, Vermont, and Maine that separate New England from Canada.

With little, if any tourist infrastructure, the Great North Woods should be an awesome adventure for anyone looking for a proper USA backcountry experience on their New England road trip.

There are a fair bit of activities in the New Hampshire part of the Great North Woods. Many of New England’s best waterfalls are in this region including the spectacular Beaver Brook Falls . There’s a very complex and thorough network of trails here as well that penetrates deep into the woods.

You can drive to Great North Woods in Maine from New Hampshire via Highway 16 and pass some excellent scenery along the way. This area is one of the best places to visit in New England in the fall because of the spectacular foliage. Be careful of moose though! These giants will run into the road sometimes and seriously ruin your car.

Maine’s North Woods is expansive and is probably the most remote part of New England. It is, in fact, so out-there that certain counties like Aroostook are not even officially incorporated into the state and so have no “official populations.”

Stories of the wood’s frightful and fantastic inhabitants still circulate to this day as well, like that of the vengeful wendigo or of the murderous ding-balls.

Interior locations like Baxter State Park and Mt Katahdin are the most “accessible” places in Maine’s North Woods. Surrounding these is 100 Mile Wilderness , which is often visited by ACT hikers. If you want to travel further than these locations you may need a 4×4 as paved roads are no longer guaranteed.

If you can make it, the Allagash Wilderness is one of the great river adventures in America. Navigable only by canoe or raft, there is nothing out here besides moose, fish, and untouched landscapes.

A road trip through New England ain’t going to be cheap, folks. With the high costs of living and high demand, New England has some of the steepest hotel rates and dining prices in the USA.

That’s no reason not to visit New England in the first place though! You have us, after all. 🙂

We at The Broke Backpacker are constantly looking for new ways to save on travel and have a whole repertoire of useful tips to share with y’all. Even if we are unable to travel for $10/day like in our favorite countries (let’s be real here), we can at least help you minimize expenses to the utmost degree.

The average daily budget for a New England road trip is between $200-$250 – this includes gas, a rental car, lodging, food, drink, and entry fees.

On any road trip, New England or otherwise, the largest cost will be gas . This expense will always sneak up on you because it can be difficult to properly gauge how much you will actually use.

Lodging is also expensive in New England. Try and camp out as much as possible to lower your daily budget significantly. Take advantage of the cheaper public campsites and occasional backcountry site, which are sometimes free. Stay in hostels as well – they’re not so bad in New England.

Food costs are something you can control as you will have the option of cooking cheaply at home or the campsite. Dining is expensive in New England so be picky about how many lobsters you eat and clam bakes you attend.

Below is a breakdown of the average costs of a road trip in New England.

Average Costs of a New England Road Trip

Rental car : $50-$150

RV rental :  $100-$300

Gallon of gas:  $2.74

Private AirBnB home:  $140

Hotel room:  $150

Hostel:  $25-$35

Campground:  $10-30 (sometimes free!)

Sandwich:  $6-$9

Beer at a bar:  $5-$8

Coffee:  $3-$4

Bottle of Whiskey from the market:  $25

Dinner for two:  $35-$60

Best Places to Stay in New England on a Budget

Camping in new england.

Camping in New England is either done on public land, private land or in the backcountry . Each type offers different sorts of amenities and at different prices.

Private campgrounds usually have more amenities and can accommodate more types of campers. RV parks, hookup sites, and other sorts of demanding camping (we hesitate to use the word “glamping”) are usually found at private camps.

Private camps usually have lots of communal facilities like a kitchen and showers. Because of their greater comfort, private campgrounds are usually more expensive.

Camping on public land, run either by the state or the feds, is usually more basic. Electricity is possible as is the occasional shower but don’t expect the resort-like services that private campgrounds have. Fortunately, prices are far more reasonable at public campgrounds.

Both public and private campsites fill up quickly in the fall. Many take reservations though and we suggest you do this if you’re going on a fall foliage road trip in New England.

Backcountry campsites, being located on either private or public land, are harder to access but have the benefit of being extremely cheap if not totally free . These campgrounds usually require a hike or maybe a water taxi to reach, which makes them difficult and unattractive for the average camper.

The backcountry campgrounds are also very primitive, often with no restrooms and maybe running water. For the intrepid, these campgrounds can be very ideal as they’re super quiet, wild, and, as previously mentioned, usually free!

Backcountry campsites are usually found in the mountains, around the lakes, and on the remote islands of New England. Use this search engine for a compendium of free camping in New England .

Always have of plenty of powerful bug spray and mosquito repellent on you. Mosquitoes are a plague in the summer. Be sure to also wear long clothing to protect yourself from ticks when hiking in the backcountry. Local ticks often carry Lyme Disease, which is an autoimmune disorder with no cure.

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Renting a Car or Campervan in New England

Renting a car is the most popular way of getting around New England. 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 and travel in a campervan , 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. We suggest booking a campervan with Outdoorsy as they usually have a good selection and good prices.

Make sure you also 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.

The roads in the Northeast are generally very good and a sedan or economy car should deliver you to most of New England’s top destinations. Only in the most remote portions of the Great North Woods, will the roads be so bad that you need 4×4 or at least high clearance.

If you’re on a road trip in New England during the winter and want to go to the mountains, you will definitely need all-wheel or 4-wheel drive.

Getting Insured for a Road Trip through New England

Concerned about staying safe in the USA? Well don’t be! Just make sure you’re insured, and you drive carefully.

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!

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New England is no doubt one of the most idyllic regions of the US. Quaint coastal towns and some of the best foliage in the country are but two reasons to take a road trip here–but there are so many more.

Hopefully, you now feel more prepared on where to go and what to do on YOUR New England road trip.

But rest assured that regardless of which spots you’re bound to find beauty, history and a whole lot of delicious seafood.

So what are you waiting for? The open, rural roads of New England awaits!

Updated February 2023 by Samantha Shea

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Wow! great article and suggestions.

thank you for all of the advinces it helps, can t wait to visit New England Vermont Maine, xxx

Lake placid in the Adirondack Mountains also a try while stop. There are several private and New York State campgrounds nearby.

Thank you for mapping this all out. I live in New England and would love to visit many of these places.

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The ultimate 10-day new england road trip itinerary.

New England, with its quaint villages, idyllic landscapes, rich history, and mouthwatering culinary experiences, is a treasure chest of delights waiting to be unlocked. From the rugged beauty of the Maine coastline to the vibrant, artistic vibe of Providence, this is a region that never fails to enchant.

If you’re up for the crisp smell of the ocean mingled with pine trees, the rustic charm of cobblestone streets lined with centuries-old houses, and the taste of the most succulent seafood freshly plucked from the sea, then you have to start planning your New England road trip!

» You might be interested in a shorter version with this Boston to Bar Harbor road trip itinerary.

» Looking for more travel inspiration in the United States ? See our U.S. Summer Vacation Ideas and 12 U.S. National Parks to Visit . Here are a few more fabulous U.S. Cities to visit .

The only real problem is deciding what to do and see and how to fit everything into ten days. Lucky for you, we’ve done this road trip multiple times and have passed through these states on a number of different trips, so we have the knowledge to help you plan an amazing time on one of the best road trips in the United States .

Table of Contents

Essential New England Road Trip Info

Comprising six states – Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont -there’s a lot of ground to cover during a New England driving tour. It’s not a small amount of driving, despite how close together many of these states are. So if you’re planning to embark on this road trip, keep this in mind.

You can either fly into a set starting point – we recommend Boston – or you can drive in from where ever you’re located in the United States. In any case, you’re going to need a car – either your own or a rental car . If you’re renting, we suggest going through Discover Cars to get the best deals from all the top car rental companies in one place.

How to Get to New England

If traveling from Europe or another destination outside the States, you’ll fly into Boston for this itinerary. Considering the region’s most popular international airport, Boston Logan International Airport (BOS) is where your trip will start and end.

If Boston doesn’t work for you, you can also fly into New York City , Philadelphia, or even Washington, DC. It will just take you a little longer to drive to the start point of this road trip, but there is plenty to see along the way.

When Should You Do on a New England Trip?

Unless you’re a winter die-hard, the best time to visit New England is undoubtedly during the fall, from September to December, or spring, from March to June. 

Fall is when the landscape takes on a magical element with changing colors in every shade of gold, orange, red, and brown imaginable. Aside from that, the crisp, clear fall air and the New England sun bursting through the morning mists are second to none, making it one of the best fall destinations in the USA .

If you can’t swing a fall road trip, the second best time is during spring. This is before the heat of the summer really sets in, so temperatures will be mild and enjoyable. I would definitely not go in summer, if at all possible, because it can get really hot and humid.

New England Road Trip Itinerary

Are you ready to buckle up and join me on a 10-day road trip across these six picturesque states? I’m thrilled to share this thoroughly curated itinerary that will ensure you make the most out of this journey, exploring the hidden gems as well as the must-see spots.

Whether you’re a history buff, a foodie, a nature enthusiast, or simply someone who enjoys the thrill of exploring new places, this 10-day New England road trip has something for everyone. So pack your bags, put on your favorite road trip playlist, and let’s hit the road.

Boston, Massachusetts (Day 1)

After arriving in Boston, Massachusetts , you can jump directly into the first day of your trip by visiting Boston. Drop off your bags at the hotel and explore Beantown (as it’s locally known). 

In a city defined by a rich history and vibrant sports culture, you’ll find a million historical things to see alongside plenty of sports bars to grab a beer in at the end of your day. While there’s no way to see the best of Boston in one day, we suggest you include these highlights on your first day:

• Walk the Freedom Trail past some of the most important sites that shaped the American Revolution
• Explore the Boston Tea Party Ships and Museums
• Head to the Italian cuisine-filled North End of Boston for either lunch or dinner
• Grab a few snapshots of America’s most photographed street, Acorn Street
• Visit the Boston Library and marvel at its exquisite architecture

Where to stay: The Newbury Boston

Salem, Massachusetts & Portland, Maine (Day 2)

Your second day of this New England vacation itinerary involves the first stretch of road to tackle. Heading out north via the Essex Coastal Scenic Byway (or Route 127), you’ll drive for about 40 minutes to reach Salem.

Infamously known for being the site of the Salem witch trials of 1962, the town is a global epicenter for everything occult. If you’re visiting during October, prepare for an overload of everything spooky. No matter when you’re in town, here are some spots you shouldn’t skip:

• The Salem Witch Museum
• Salem Witch Trials Memorial
• The House of the Seven Gables

When you’re done exploring spooky Salem, jump back on Route 127. After about an hour and forty minutes, you’ll reach Portland, Maine. 

Similar to its west coast counterpart in Oregon , Portland, Maine, is a city with a bustling passion for the arts, the outdoors, and local microbrews and distilleries. Arriving in the city, you can leave your bags at your hotel and set out for a taste of Portland.

Some of the top things to see and do while you’re in town include:

• Visit Fort Williams Park and the Portland Head Light
• Tackle a brewery tour of Portland to some local craft breweries
• Shop the local boutiques and specialty shops of Old Port
• Grab a sunset view along the Eastern Promenade
• Eat lobster rolls at Luke’s Lobster on the pier

Tours to look out for while you’re in Portland:

• Old Port Culinary Walking Tour
• Cusco Bay Sea Kayaking Tour
• A Walk Through Time Tour in Portland 

Where to stay: Portland Regency Hotel & Spa

Bar Harbor & Acadia National Park, Maine (Day 3)

Your third day along this New England trip requires an early start and a three-hour drive, but the rewards are totally worth it. Driving from Portland to Bar Harbor, the beach town gateway to Acadia National Park, prepare for some out-of-this-world scenery.

Along the route, you’ll pass through a few towns worth a stop. The first is Bristol, where you can spend a minute or two at the Pemaquid Point Lighthouse , then stop at the Camden Hills State Park in Camden to see the view from the top of Mt. Battie.

After dropping off your belongings at your overnight spot in Bar Harbor, it’s time to head into Acadia National Park. You need a U.S. Park Pass to get in. If you’re going to be visiting more than one park in the year, you should definitely consider getting the America the Beautiful annual pass, which is just $79.99 from REI.

On Maine’s largest island, Mount Desert Island, the 47,000-acre Acadia National Park has dramatic mountains, picturesque lakes, and endless miles of hiking trails. It’s one of the biggest draws to this part of the U.S.

The top three things to add to your Acadia itinerary include:

• Hiking to the summit of Cadillac Mountain (vehicle reservations are required for Cadillac Summit Road from May 25 through Oct 22). Book online.
• Kayaking on Swan Lake
• Biking or driving the Park Loop Road. The Park Loop Road can be very crowded. Have a backup plan if the area you wish to visit is full.

Where to stay: Bar Harbor Inn

White Mountain National Forest, New Hampshire (Day 4)

While you technically did venture into stunning New Hampshire earlier in your road trip, day four is all about heading to and roaming around one of the state’s top attractions. The drive to get there is another 3 hours 30 min drive, so get up early!

Topping most driving tours of New England, especially those focused on New Hampshire, White Mountain National Forest is a beautiful collection of natural landscapes. The best thing about the National Forest is that there are many unique activities to indulge in regardless of what time of year you’re visiting.

• In springtime, thanks to warmer weather and melting snow, the forest delivers the perfect setting for hiking and camping.
• During the summer, you can fill your day by hiking, fishing, or canoeing.
• When fall arrives, you should set out to drive New Hampshire’s scenic Kancamagus Highway.
• Wintertime brings with it a lot of snow-capped mountains fit for winter sports enthusiasts at numerous ski resorts.

Where to stay: The Inn at Thornhill & Spa

Stowe, Vermont (Day 5)

Once you’ve said farewell to New Hampshire, it’s time to head to NEK or the North-East Kingdom of Vermont. It’s a 1 hour 30 minute drive. Known for its spectacular green mountains, eye-catching lakes, and charming small farms, the state is a buzzworthy must-visit.

On the way to Stowe, you’ll stop in Waterbury for a genuine pilgrimage to the ice cream empire and the original store of Ben & Jerry’s.

Next up is a short 20-minute drive north to the ski resort town of Stowe. This world-famous ski destination showcases an authentic small-town charm, a lively main street, and some iconic steepled churches.

Be sure to check out some of Stowe’s one-of-a-kind local favorites, such as Laughing Moon Chocolates, Shaw’s General Store, and The Deep End (the hippest pizza place in the state). Other options here include:

• Skiing at the Trapp Family Lodge
• Hiking in Green Mountain National Forest
• Heading on a scenic drive on Mountain Road

Where to stay: The Lodge at Spruce Peak

Litchfield & Mystic, Connecticut (Day 6)

Another early start on day six, you’ll drive down the Route 100 Scenic Byway, Vermont’s longest highway, through Wilmington, across the border into Connecticut. First stop of the day? Litchfield; a charming New England town brimming with local history. It’s a 4-hour drive to get there.

Founded in 1719, today, the town is a popular tourist destination known for its antique shops, numerous art galleries, and historic homes.

Delving further into Connecticut, you’ll head east to the town of Mystic. This historic seaport sits snuggly on the Mystic River and is most famous for its maritime heritage and the setting of the 1988 film Mystic Pizza .

Here are some highlights in Mystic:

• Visit the Mystic Seaport Museum , one of the largest in the world
• Explore early colonial farm life at the Denison Homestead
• Dive into some aquatic adventures at the Mystic Aquarium
• Hike a trail or two in Bluff Point State Park

Where to stay: Hilton Mystic

Newport, Rhode Island (Day 7)

Continuing the coastal New England road trip, the next stop along your journey is in Rhode Island. Although it’s the smallest state in the US, it is home to some of the country’s most historic towns, most notably Newport. This is only an hour drive.

This seaside town, once a summer retreat for America’s most wealthy families, boasts breathtakingly stunning mansions built during the Gilded Age and is quite the sight to behold. Beyond that, you’ll find pristine beaches and some of the best seafood in the country here.

When you’re planning your day in Newport, be sure to include these must-do activities:

• Stroll along Cliff Walk, a coastal 3.5-mile pathway hugging the Atlantic Ocean
• Indulge in some retail therapy along Bellevue Avenue and Thames Street
• Head out wine tasting at Greenvale Vineyards
• Tour the famous Newport Mansions
• Explore Bowen’s Wharf or take a boat cruise from Long Wharf
• Relax on the sands of Easton Beach

Where to stay: Newport Marriott

Cape Cod (Day 8)

Next up, and after an entire week on the road, it’s time for some rest and relaxation on the flexed arm of Massachusetts, in Cape Cod, a 1-hour 30-minute drive. Sitting on a peninsula in the state’s southeastern region, Cape Cod has long been a summer destination for the rich and famous.

Now if you’ve ever wondered why New England beach vacations are so popular, the almost 560 miles of coastline that encircle Cape Cod provide a clear answer. Yes, there are many great towns here worthy of a stay, but for this road trip, you’ll spend the day and night in Sandwich.

The official oldest English settlement in Cape Cod, Sandwich, dates back to 1639 and stuns with calm beachfront, quaint eateries, and a vibrant historic district. Fill your day in Sandwich with some of these standouts:

• Breakfast at Cafe Riverview
• Stroll along East Sandwich Beach
• Visit Sandwich Boardwalk
• Explore the Sandwich Historic District
• Indulge in the best lobster in town at Mattakeese Wharf

Where to stay: Sandwich Lodge & Resort

Plymouth, Massachusetts (Day 9)

What would an itinerary for a New England road trip be without a stop in Plymouth? That’s why your second-to-last day in the area is all about exploring the town that dates back to 1620. It’s a 30-minute drive from Cape Cod.

Today this quintessential New England town is most known as the site where the very first Thanksgiving took place and is home to Plymouth Rock. Steeped in history, this is where the Pilgrims first landed way back when.

With all that history, here are a few top spots you should visit while in Plymouth:

• Explore Plimoth Patuxent , a living history museum with a replica of the Mayflower ship
• Grab a few snapshots at Plymouth Rock and delve into the Pilgrim Hall Museum
• Roam around Plymouth’s historic downtown harbor area, home to several notable buildings such as the Plymouth Courthouse
• Cap off your day with a stroll along Plymouth’s famously historic waterfront and catch the sunset over Cape Cod

Where to stay: Thomas Sea Suites at Harbourtown

Boston, Massachusetts (Day 10)

Finally ending your epic 10-day New England road trip, you’re back in Boston . Luckily the drive from Plymouth to Boston is only 45 minutes to an hour, so you can start the day a bit later and still be back in Beantown with some time to spare for any extra activities.

We’d recommend fitting anything you didn’t have time for on day one into your final day. If you’ve got a few extra hours, here are some other Boston highlights to add:

• For history lovers, pay a visit to the USS Constitution Museum or the Paul Revere House
• Art lovers should definitely head to the Isabella Stewart Gardner Museum and the Museum of Fine Arts
• Sports fanatics should take a one-hour tour of Fenway Park or catch a Boston Red Sox game ( check their calendar here )
• For food lovers, be sure to check out our foodie guide to Boston .

Where to stay: Hyatt Centric Faneuil Hall Boston

Wrapping Up Your Road Trip Through New England

There you have it – the best road trip through New England you could possibly do in ten days. Although numerous other attractions and standout activities can be included on any trip, this New England trip itinerary features the best of the best.

Of course, you can play around with other vacation ideas in New England or discover hidden travel tips heading off-the-beaten-path. Now all you have to do is decide when to go and prepare for some exciting road-tripping in New England.

Be Prepared For Travel Planning is the most important part of any successful trip. Do it the easy way:

🧳 Travel Packing List | ✔️ Why You Need Travel Insurance | ✈️ What to Do Before You Leave Home

• Find and book the best hotel (our favorite booking site is Expedia)
• Research flight options (our favorite tool is Skyscanner )
• Book a tour (we always use Viator to find the best tours)
• Rent a car through Discover Cars (they search the best deals for you!)

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Laura Lynch, creator and writer of Savored Journeys, is an avid world traveler, certified wine expert, and international food specialist. She has written about travel and food for over 20 years and has visited over 75 countries. Her work has been published in numerous guidebooks, websites, and magazines.

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9 New England Road Trip Itineraries for Any Season

Whether it’s spring, summer, fall, or winter, there’s a road trip (or two) for each season..

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View of Horsehead-Marbella, an historic house near Beavertail State Park.

Photo by Trevor Fairbank/Shutterstock

New England may be known for its autumn reds and yellows, but to us, there’s no bad time to cross the region by car. Officially consisting of the six states of Maine , Vermont, New Hampshire, Massachusetts, Connecticut, and Rhode Island, New England is filled with picturesque seaside towns, mountains, clear lakes, and yep, some of the best fall foliage around. To see the region’s most beautiful sites, head out on one of these great New England road trip itineraries.

1. Vermont 100

• Start: Heartwellville
• Distance: 200 miles
• Recommended season: summer

At 200 miles long, the Scenic Route 100 Byway hugs the eastern edge of the Green Mountains and travels nearly the entire length of Vermont. (Most of Vermont’s ski resorts are located along the highway, so it can actually have fewer cars in the summer than winter.) Cute country stores your thing? Be sure to stop at Vermont Country Store in Weston—it’s been open since 1946 and offers free cheese and maple syrup samples.

Dramatic scenes like these are par for the course along Maine’s coast.

Photo by Shutterstock

2. Coastal Maine

• Start: Ogunquit
• End: Calais
• Distance: 272 miles

Much like California , Maine is also known for its stretch of Route 1, aka “the lobster trail.” This trip crawls along the coastline and passes through Ogunquit, Kennebunk, Portland, Rockport, and more until it hits Canada. Must-dos along the way: Eat at the Clam Shack , on the bridge between Kennebunk and Kennebunkport, snap a photo for the ’gram at Portland Head Light, and visit Project Puffin Visitor Center in Rockland—especially fun with kids in tow.

Cape Cod is known for its beautiful beaches and coast line.

VALORIE DARLING/Valorie Darling

3. Old King’s Highway in Cape Cod

• Start: Sandwich
• End: Provincetown
• Distance: 60 miles

Route 6A is popular in summer, when visitors to the Massachusetts Cape begin their trip in Sandwich and follow the road east to Provincetown, passing cranberry bogs, salt marshes, historic homes, and some of the oldest villages in the United States. Get your lobster roll fix at places like Kate’s Seafood (Brewster) and Arnold’s Lobster & Clam Bar (Eastham). For overnights, head over to South Dennis and stay at the Sesuit Harbor House , originally built in 1735.

The Kancamagus Highway is known for being one of the top spots to see fall foliage.

4. Kancamagus Highway, New Hampshire

• Start: Conway
• End: Lincoln
• Distance: 34.5 miles
• Recommended season: fall

Curving for 34.5 miles on country roads through New Hampshire’s White Mountain National Forest, this drive has earned its place on several “best of” road trip lists, thanks to its picturesque ponds, hiking trails, scenic overlooks, and hairpin turns. Colloquially known as the “Kanc,” the byway draws millions of visitors every year. With the highway’s plentiful hiking trails taking up daylight, spend the night in one of the six White Mountain National Forest campgrounds located on the byway.

This road trip passes through quaint towns like St. Johnsbury, Vermont.

SNEHIT PHOTO/Shutterstock

5. Connecticut River Byway

• Start: South Hadley, Massachusetts
• End: Pittsburg, New Hampshire
• Distance: 242 miles

Another way to reach New Hampshire’s White Mountains is to take the Connecticut River Byway , which is Vermont’s only designated National Byway. Along the way, stop by some of Massachusetts’s historic district villages like Northfield and Montague Center, or take some nature-led detours to Molly State Park in Vermont.

If you’re unable to do the whole route, no worries. In the words of AFAR editor Tim Chester : “Pick a stretch and you can’t go wrong—particularly in fall when the leafy backdrop is painted shades of red, orange, and yellow.”

End your road trip in Burlington, Vermont’s capital.

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6. Burlington to Woodstock, Vermont

• Start: Burlington
• End: Woodstock
• Distance: 132 miles

While several road trips on this list go through Vermont, this road trip itinerary specifically focuses on the state’s delicious dishes . Starting in Burlington, road-trippers can visit the local farmers’ market for breakfast before continuing south on Route 89 to Stowe. Around here, try concepts like Long Trail Brewing Company and Hen of the Wood. The drive concludes in Woodstock, offering local fare from Fat Toad Farm.

7. Mohawk Trail, Massachusetts

• Start: Pittsfield
• End: Greenfield
• Distance: 63 miles

Massachusetts’s Berkshire Mountains and its famed 63-mile Mohawk Trail are the stuff of leaf-peeping legends . Starting in Pittsfield, take Route 7 north until hitting Williamstown, home to Williams College, and continue on Route 2 to Western Gateway Heritage State Park, Natural Bridge State Park, and MASS MoCA, among other attractions. Eventually, you’ll hit the Hoosac Range—where the views only keep getting better. For a stay along the way, consider the Tourists hotel in North Adams.

Winter in Stowe, Vermont, one of the leading ski destinations on the East Coast

8. Skiers’ Paradise, Vermont

• Start: Stowe
• Distance: 80 miles
• Recommended season: winter

Come winter, heavy snow drifts mean good things for skiers in New England. Visit two of the best ski resorts on the East Coast on this road trip, which starts in Stowe and finishes in Woodstock, Vermont. It’s a mere 80 miles between the two towns, but the slopes—and attractions—in each mean you’ll want to spread the trip out over a long weekend. Things not to miss in Stowe: the family-run Alchemist brewery, Stowe Maple Products sugarhouse, and the thin-crust pies at the aptly named Piecasso .

In Woodstock, be sure to carve out time for Richardson’s Tavern , Billings Farm & Museum , and F.H. Gillingham & Sons , a store that has been open for more than 130 years.

9 . Quiet Connecticut

• Start: Norwich
• Distance: 40 miles
• Recommended season: spring

If you’re a fan of quaint towns and farmsteads, this road trip from Norwich to Woodstock might be for you. (Fun fact: Woodstock has more dairy farms than anywhere else in the state.) The road clocks in at 40 miles, you’ll want to slow down and take your time—yep, it’s that scenic. Do some birdwatching at Aicher Preserve or Border Woods Preserve before staying at the Inn At Woodstock Hill , where you can enjoy Connecticut’s serenity near the small town of Putnam. Tranquility, is that you?

This article originally appeared online in 2020; it was most recently updated on August 9, 2023, to include current information.

The Ultimate 5 Day New England Road Trip Itinerary

Hello, fellow road trippers! Are you ready to embark on a picturesque journey through New England? This 5-day New England road trip itinerary is designed to show you the best of this region’s charming towns, stunning landscapes, and rich history. As someone who loves hitting the road and has a soft spot for New England’s unique allure, I’m thrilled to share this journey with you.

Day 1: Boston, Massachusetts – The Historic Start

Starting Point – Boston : Begin your New England adventure in Boston, a city steeped in history and culture. Spend your morning walking the Freedom Trail , a 2.5-mile route that takes you to 16 historically significant sites. Don’t miss the Boston Common, the United States’ oldest public park.

Afternoon Exploration : In the afternoon, explore the cobblestone streets of Beacon Hill, known for its beautiful Federal-style rowhouses and quaint atmosphere. Enjoy a meal at one of the local eateries – Boston’s culinary scene is a delightful mix of traditional New England fare and modern cuisine.

Evening in Boston : As evening falls, head to the Boston Harbor or stroll along the Charles River Esplanade for stunning city views.

Day 2: Boston to Cape Cod, Massachusetts – Coastal Charm

Morning Drive to Cape Cod : On your second day, head to Cape Cod, a hook-shaped peninsula known for its quaint villages, seafood shacks, Martha’s vineyard and lighthouses. The drive from Boston to Cape Cod is about 1.5 hours, but take your time and enjoy the scenic journey.

Exploring Cape Cod : Once in Cape Cod, visit the Cape Cod National Seashore for its beautiful beaches and walking trails. Check out Provincetown for its art galleries and vibrant street life.

Overnight in Cape Cod : Spend the night in one of Cape Cod’s charming inns or bed and breakfasts, experiencing true New England hospitality.

Day 3: Cape Cod to Newport, Rhode Island – A Touch of Elegance

Journey to Newport : On day three, travel to Newport, Rhode Island, renowned for its stunning Gilded Age mansions and sailing culture. The drive takes about 1.5 hours, offering beautiful coastal views along the way.

Discovering Newport : In Newport, tour The Breakers, the grandest of Newport’s summer “cottages” and a symbol of the Vanderbilt family’s social and financial preeminence in the Gilded Age. Stroll along the Cliff Walk, a 3.5-mile path that offers spectacular ocean views on one side and opulent mansions on the other.

Evening Leisure : Enjoy an evening in Newport’s historic downtown, dining by the waterfront and savoring fresh local seafood.

Day 4: Newport, Rhode Island to White Mountains, New Hampshire – Into the Wilderness

Morning in Newport : Start your fourth day with a leisurely morning in Newport. Perhaps take a sail around Narragansett Bay or explore more of the town’s historic streets and shops.

Drive to the White Mountains : Mid-morning, begin your journey north to the White Mountains in New Hampshire. This drive takes you into the heart of New England’s natural beauty. The journey is about 4 hours but feels shorter due to the stunning scenery along the way.

Exploring the White Mountains : Upon arrival, immerse yourself in the natural splendor of the White Mountains. Visit Franconia Notch State Park, where you can see the Flume Gorge, a natural granite gorge extending 800 feet at the base of Mount Liberty. The Cannon Mountain Aerial Tramway offers breathtaking panoramic views.

Overnight in the Mountains : Spend your night in a cozy mountain lodge or cabin. The White Mountains region offers various accommodations, from rustic to luxurious, allowing you to enjoy the serene mountain atmosphere.

Day 5: White Mountains to Portland, Maine – A Coastal Finale

Morning Hikes and Scenic Views : Wake up early to catch a sunrise in the mountains. If you’re up for it, enjoy a morning hike; there are trails for all skill levels, offering one last chance to soak in the natural beauty of New Hampshire.

Journey to Portland, Maine : After your morning in the mountains, set off for Portland, Maine, about a 2-hour drive. This charming coastal city is known for its vibrant arts scene, historic Old Port waterfront, and incredible seafood.

Discovering Portland : Spend your afternoon exploring Portland’s cobblestone streets, unique boutiques, and art galleries. The Portland Head Light, a historic lighthouse in nearby Cape Elizabeth, is worth a visit for its picturesque setting.

Evening in Portland : Conclude your New England road trip with a delightful dinner in Portland. The city’s culinary scene is a fusion of traditional New England flavors and innovative cuisine. Enjoy a meal at one of the waterfront restaurants, savoring the fresh catch of the day.

Reflecting on Your New England Road Trip

Your 5-day New England road trip itinerary has taken you on a journey through some of the most picturesque and culturally rich parts of the Northeast. From the historic streets of Boston to the coastal beauty of Cape Cod and Newport, the majestic White Mountains, and the charming city of Portland, you’ve experienced a tapestry of landscapes and lifestyles that make New England unique.

As you head home, you carry with you not just photos but memories of quaint towns, scenic drives, and the warm hospitality of the Northeast. This trip is more than just a journey through places; it’s an exploration of the heart and soul of New England.

I hope this itinerary inspires you to explore the diverse beauty of New England. Safe travels, and may your road trips be filled with discovery and joy. If you need any more tips or insights for traveling in New England or beyond, feel free to reach out. Happy travels!

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The Ultimate New England Road Trip Itinerary

Get acquainted with the birthplace of America on a New England road trip. Discover the quaint coastal towns, famous historical landmarks, and spectacular scenic drives the area has to offer. Our trip includes additional states, but the bulk of our itinerary is in six states: Connecticut, Rhode Island, Massachusetts, New Hampshire, Maine, and Vermont.

It’s for 60 days, starting and ending in Chicago and driving roughly 2,500 miles, but you can adjust it to your liking. Visit one national park, too-many-to-count lighthouses, a few state parks, picturesque small towns, and overindulging on copious amounts of seafood along the way.

If you are looking for more unforgettable adventures, check out these trips: Chicago to L.A. via Route 66 , hiking 500 miles on the Camino in Spain , and a cross country road trip to thirteen national parks.  

When to Visit New England

From our experience and research, there really is no bad time to visit New England. Each season brings something unique to the table.

Winter is cold and snowy but perfect for winter activities such as skiing and snowboarding. The thawing temperatures of spring bring wildflowers and maple syrup. Summer is known for its hot weather and sunny days filled with outdoor adventures. And last but not least, fall welcomes a blanket of blazing colored treetops and great hiking temperatures.

WAIT UNTIL YOU READ WHAT WE HAVE PLANNED! SCROLL DOWN FOR MORE INFO

One of the Top Spots for Fall Foliage in the U.S.

So why did we choose New England this trip? We have had an east coast road trip on our radar for quite some time and especially wanted to visit during the fall. It is touted as one of the best locations for fall foliage in the United States.

Donned in our heavy sweaters as autumn unfolds with rich colors of crimson and gold with the smell of fire and a hint of pumpkin spice floating in the air, I can’t imagine a better time.

Hopefully, from mid-September until the end of October, we will be leaf peeping fools.

Ultimate New England Road Trip Itinerary Summary

Keep Scrolling for our detailed New England Self Drive Itinerary.

Summary starting and Ending in Chicago, Illinois

• Put-in-Bay, Ohio (2 nights)
• Erie, Pennsylvania (1 night)
• Watkins Glen State Park, New York (3 nights)
• Litchfield, Connecticut (1 night)
• Hartford, Connecticut (2 nights)
• New Haven, Connecticut (1 night)
• Niantic, Connecticut (1 night)
• Mystic, Connecticut (2 nights)
• Block Island, Rhode Island (1 night)
• Portsmouth, Rhode Island (2 nights)
• Providence, Rhode Island (2 nights)
• Provincetown, Massachusetts (1 night)
• Falmouth, Massachusetts (1 night)
• Martha’s Vineyard, Massachusetts (3 nights)
• Plymouth, Massachusetts (1 night)
• Salem, Massachusetts (1 night)
• Hampton Falls, New Hampshire (1 night)
• Kennebunkport, Maine (1 night)
• Acadia National Park / Bar Harbor (8 nights)
• Bangor, Maine (2 nights)
• Baxter State Park, Maine (3 nights)
• Lily State Park, Maine (2 nights)
• White Mountains, New Hampshire (6 nights)
• Burlington, Vermont (2 nights)
• Stowe, Vermont (2 nights)
• West Dover, Vermont (7 nights)
• Buffalo, New York (1 night)
• Chicago, Illinois

Day 1: Chicago, Illinois to Put-In-Bay, Ohio

We leave Lake Michigan to head over to Lake Erie, the southernmost lake of the Great Lakes. It is also the shallowest which makes its water temps the warmest.

Our first stop is Put-In-Bay, a small village on South Bass Island. Known for its party-hearty culture, we are determined to not only imbibe a bit but also to discover the hidden gems on the island.

Driving Info: 279 miles, 5 hrs 20 minutes with a ferry ride

READ NEXT: TOP 10 THINGS TO DO IN PUT-IN-BAY

Day 2: Put-In-Bay, Ohio to Erie, Pennsylvania

We were beckoned to drive along the Lake Erie coast when we visited Cleveland a few years ago but didn’t include the ride on that trip. Up the waterline, we go, as we leave Put-In-Bay to explore the small towns and lighthouses along the way.

Who knew Pennsylvania has a sliver of land right on the lake? We stop for the night at Presque Isle State Park, a small park on a sandy peninsula that juts into Lake Erie. If you are interested in renting an RV and starting in Pennsylvania, check out RV Rental Philadelphia, the largest, most trusted RV Rental marketplace with a wide-ranging inventory.

Driving Info: 190 miles, 3 hrs 45 minutes with a ferry ride

RELATED: COOL STOPS ALONG OHIO’S LAKE ERIE COASTAL TRAIL

Days 4 – 6: Erie, Pennsylvania to the Finger Lakes, New York

The Finger Lakes region in New York is known for a series of pristine lakes and beautiful vineyards. The area is also home to a number of hiking trails, breweries, distilleries, and hard-cider producers.

Driving Info: 198 miles, 3 hrs 15 minutes

READ MORE: 3 DAY FINGER LAKES ITINERARY

Day 7: Finger Lakes to Litchfield Hills, Connecticut

Ever heard of the television show, Gilmore Girls ? Today, we reach our first New England state, Connecticut, where the fictional town of Stars Hollow was based on. We are touring the northwest hills in search of magical towns like Washington, New Milford, Bantam, and Litchfield which inspired the creators of the show.

Driving Info: 297 miles, 5 hrs

RELATED: A CONNECTICUT BUCKET LIST FOR YOUR NEXT TRIP

Days 8 & 9: Litchfield Hills to Hartford, Connecticut

And we are off to the state capital of Hartford, one of the oldest cities in the United States. Founded in 1635, we are bound to find some historical places to visit. A few on the list so far are Trinity College, Wadsworth Art Museum, and Bushnell Park.

The one I’m most excited about is the Mark Twain House where he wrote some of his most famous works and raised his family.

Driving Info: 32 miles, 50 minutes

Day 10: Hartford to New Haven, Connecticut

Let’s make our way to the water again, New Haven is situated along the Long Island Sound in southern Connecticut. It’s the first planned city in America and home to Yale, one of the oldest universities in America.

Oh and apparently, home to some of the best pizza in the country. This Chicago-born Midwesterner writes with a probably-not-side-grin. But hey, you never know!

Driving Info: 39 miles, 40 minutes

Day 11: New Haven to Niantic, Connecticut

On our way to Mystic, we plan to take a leisurely drive along the coast to dip in any beach towns with a view. At lunch, we will find our first lobster roll of the trip. The word on the street is that Connecticut’s rolls are not made with mayo, just butter and a squeeze of lemon so it’s a must-try.

Driving Info: 42 miles, 45 minutes

Days 12 & 13: Niantic to Mystic, Connecticut

Never did I imagine a New England road trip would have me hunting down pizza, but stopping at Mystic Pizza is a MUST in my eyes. My love for Julia Roberts isn’t the only reason we are stopping here, the seaside village is brimming with charm and boasts the nation’s largest maritime museum.

Driving Info: 18 miles, 25 minutes

Day 14: Mystic to Block Island, Rhode Island

With a declaration from the Nature Conservancy that Block Island is one of its “Last Great Places,” it was a given that we were going to zip our way over once we cross into Rhode Island. As if dramatic rugged bluffs weren’t enough to put us over the edge (literally and figurately), the 365 freshwater ponds and rolling green hills had us hooked.

Driving Info: 54 miles, 2 hrs 15 minutes with a ferry ride

Plan Your Trip Here: Amazing Things to Do on Block Island

Days 15 & 16: Block Island to Portsmouth, Rhode Island

Portsmouth is our base location for exploring the grandeur Newport Mansions of the social elite like the Vanderbilts and Astors. Ah, the Gilded Age, when the rich were rich and wanted everyone to know it.

After a few tours such as the Biltmore Estate and  Stan Hywet Hall and Gardens, we’ve become obsessed with these over-the-top homes. We can’t wait to stroll the Cliff Walk, a 3.5 mile National Recreation Trail that hugs the Newport shoreline offering gorgeous coastline and mansion views.

Driving Info: 46 miles, 2 hrs 11 minutes with a ferry ride

How to Choose the Best Newport Mansion Tour

Days 17 & 18: Portsmouth to Providence, Rhode Island

Cheers to hitting another state capital! Providence is the cultural hotspot of New England. With a vintage feel in a college town and the most coffee and doughnut shops per capita of any city in the country, I’m sure we’ll keep busy, or at least our mouths will.

Driving Info: 29 miles, 32 minutes

Day 19: Providence, Rhode Island to Provincetown, Massachusetts

Onward to the Cape! Cape Cod that is. And it is here where we will have one of the most anticipated experiences of the trip, a whale watching tour!

Situated at the tip of Cape Cod, Provincetown is a quirky artsy area that also happens to be a jumping point for whale watching tours.

Driving Info: 120 miles, 2 hrs 12 minutes

Day 20: Provincetown to Falmouth, Massachusetts

Today is a day for moseying around the island stopping at captivating waterfront villages and maybe a local food shack or brewery. Since we brought our bikes, we will roll onto the Shining Sea Bikeway, a 10.7-mile path that runs from the coast in Falmouth to Woods Hole and then past to North Falmouth. 

Overnight is at Falmouth so we can get an early ferry over to Martha’s Vineyard.

Driving Info: 68 miles, 1 hr 35 minutes

Days 21 – 23 Falmouth to Martha’s Vineyard, Massachusetts

Just south of Cape Cod and a short ferry ride away sits Martha’s Vineyard, a presidential getaway in my mind. I picture snazzy inns, upscale boutiques, and perfect stately homes; ritzy glamour degraded by the simplicity of the beach… where I will tell no one that our minivan turned campervan awaits us back on the mainland. Read here about all the fun things to do on Martha’s Vineyard Island. 

Driving Info: 19 miles, 1 hour 15 minutes with a ferry ride

Day 24: Martha’s Vineyard to Plymouth, Massachusetts

Advancing north, stop for an overnight at the first Pilgrim settlement, Plymouth, where I’m sure you will have mixed emotions about the small rock that marks the spot.

But the iconic landmark is not what keeps visitors coming back for more.

Driving Info: 55 miles, 2 hrs

Day 25: Plymouth to Salem, Massachusetts

If you haven’t heard of the Salem witch trials then you may be living under a rock. Plymouth rock, perhaps.

Salem is not shy about its history where the word “witch” is displayed all over town. It shouldn’t come as a surprise that a witch museum, cemetery and a house with a supernatural past are on our itinerary.

Driving Info: 64 miles, 1 hr 17 minutes

Day 26: Salem, Massachusetts to Hampton Falls, New Hampshire

Clutching the coast, swing past Manchester-by-the-Sea, Gloucester, Rockport, and Newburyport before crossing over to the next state of New Hampshire.

Make sure to detour to the Hammond Castle Museum, an exotic castle built in the early 1900s by an inventor.

Driving Info: 32 miles, 45 minutes

Day 27: Hampton Falls, New Hampshire to Kennebunkport, Maine

At 18 miles long, New Hampshire’s coastline is short-lived so progress to the state of Maine. It’s hard to believe you’ve hit five of the six New England states already!

Kennebunkport is going to be all about seafood, boats, and shopping.

Driving Info: 43 miles, 50 minutes

Days 28 – 35: Kennebunkport to Acadia National Park, Maine

It’s time for some hiking and biking! Park it in Acadia National Park for at least four days (more if you can swing it) because you’ll be in awe of the beauty around you.

Cadillac Mountain, Sand Beach, Bar Harbor, and Park Loop Road are just a few things on the list of things to see. 

Read about one of the most thrilling hikes in the Northeast that you’ll find within the park. 

Driving Info: 201 miles, 3 hrs 30 minutes

Days 36 & 37: Acadia National Park to Bangor, Maine

The main reason for our weekend in Bangor is to visit with friends, but items like a Stephen King’s house and the world’s largest Paul Bunyan statue might have you putting it on your itinerary as well.

Driving Info: 50 miles, 1 hr 15 minutes

Days 38 – 40: Bangor to Baxter State Park, Maine

Baxter State Park is home to Mount Katahdin and the end of the 2,168-mile Appalachian Trail. Take a few days to explore and hike to the peak of the highest mountain in Maine at 5,270 feet.

Driving Info: 88 miles, 1 hr 35 minutes

RELATED: SEE OUR FAVORITE FREE CAMPING APPS

Days 41 & 42: Baxter State Park to Lily Bay State Park, Maine

At Lily Bay State Park, you’ll find what’s often referred to as Maine’s crown jewel, Moosehead Lake, the largest lake in New England.

It is also known to sprout some bright fall colors and is a great area to spot moose.

Driving Info: 51 miles, 1 hr 35 minutes

Days 43 – 48: Lily Bay State Park, Maine to White Mountains, New Hampshire

The Kancamagus Highway, a 34-mile road through the heart of the White Mountains, is one of the best drives for fall foliage in the United States.

No stores, no houses – just forest; the scenic byway stretches from Lincoln to Conway.

Driving Info: 205 miles, 4 hrs 25 minutes

Days 49 & 50: White Mountains to Burlington, Vermont

Along the shores of Lake Champlain sits a vibrant city with a thriving arts scene and welcoming atmosphere. Vermont’s largest city, Burlington, has a little bit of everything.

Driving Info: 2 hrs 20 minutes

Days 51 & 52: Burlington to Stowe, Vermont

The birthplace of the infamous Heady Topper Beer from The Alchemist Brewery and a stone’s throw away from Ben & Jerry’s factory, I think I’m going to start calling Stowe, the adult playground of Vermont. 

Driving Info: 36 miles, 46 minutes

Days 53 – 59: Stowe to West Dover, Vermont

From Stowe, take the well-known Highway 100, another popular fall foliage route in New England, down along the Green Mountains.

Hopefully, those green mountains will be lit up with scarlet reds, glistening golds, and tangerine orange.

Driving Info: 147 miles, 2 hrs 41 minutes

Day 60: West Dover, Vermont to Chicago, Illinois

At this point in the trip, you could take an extra night to stop at the one and only Niagara Falls in New York. Otherwise, that’s a wrap folk!

60 days and a whole lotta unforgettable memories!

TIP: For those of you that would like to close the loop, head further south to the Berkshires of Western Massachusetts. A popular destination for fall foliage, cultural attractions, and outdoor fun. 

Driving Info: 13 miles, 13 hrs 36 minutes

See Below for a Map of the New England Road Trip Itinerary.

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Do you have any additions to our New England road trip itinerary? Let us know in the comments below!

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Save this Northeast Road Trip Itinerary for later! 

• About Author
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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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13 Responses

So, I’m a fan of this trip. You had me at Gilmore Girls, Mystic Pizza and then solidified how much we are connected with Salem and Bangor.

I have wanted to do a Fall Foliage trip like this forever. I think I might try to make this happen one year…soon. I can’t wait to see your photos on the IG.

Dang Travelers

It has been on our list of places to get to for awhile now so we are ecstatic to finally be making it happen. I’m cracking up because when I (Angela) was making the itinerary I totally watched a few Gilmore Girls episodes and the movie, Mystic Pizza to get pumped! Leaving the GG reference out to Save though. He didn’t know that’s why I planned that area until a few days ago! LOL We will get started on all your planning so all you have to do is find the time. Thanks for following Kristi!

You didn’t include Mt. Washington and the cog railway. You should try to hit they in!!! I think you’re gonna love Block Island, Burlington, Acadia. The coast of ME. Mystic is nice. Portsmouth, RI has a ride the rails along the waterfront. Check that out. Too bad you are missing Boston!

We will be hitting Mt Washington in the White Mountains but didn’t know about the cog railway! So excited to explore Rhode Island and Connecticut or shall I say #47 and #48 of my states list. Dave really wanted to go into Boston but figured we could do it on another trip when we fly in. Always expensive and difficult to worry about parking in big cities but othwrwise we would have loved to. Thanks for the tips Cheryl!

Your trip sounds awesome. I cannot wait for all the pictures and to hear all about it. I would make a detour in Maine and stop in Freeport, Maine and go to LL Bean store. It is an absolute must see. It is open 24 hours (at least it used to be) and there are 9 floors and each one is better/more exciting then the next. It isn’t just clothes either. My husband enjoyed it as well and he isn’t a shopper.

Top Things to Do on Block Island: A Travel Guide – Dang Travelers

[…] SEE OUR ENTIRE 60 DAY ITINERARY […]

Found your trip itinerary and will definitely be putting it to use! Not too often do you find trips starting in the Midwest! I just went through and copied and pasted all the trip info you suggested. Or is there a printable version of this that I completely missed somewhere? Thanks so much for sharing!

Hi Nicole! I do not have a downloadable itinerary as of right now. Sorry, hopefully copying worked just fine. You’ll love it out east!

Cheryl Archambault

For anyone wanting to specifically see the foliage start in farthest north of New Hampshire generally around the 3-4 week of September. Foliage is peak around Concord during Columbus Day Weekend; but cool or rainy weather can change that. Encourage you to take a jacket and go up the Cog Railway to the top of Mt. Washington. It could be covered in snow there! In Rhode Island Block Island is lovely. Ferries leave from Pt. Judith or Newport. Newport is lovely and don’t miss seeing Waterfire in Providence. Acadia National Park and Bar Harbor and Boothbay is wonderful. East to west Vermont in Fall is a dream. Rte2 is a very scenic ride.

Thanks so much Cheryl!

my husband & I want to do an abbreviated version of your trip. What time of year did you do this trip? I have heard Sept is the best time for lobster but Oct is the best time for foliage.

We started right after labor day in September but took about 3 months. That year the fall color was starting to come in late September and lasted through the third week of October. Inland and lower elevations started earlier with Acadia National Park at peak around the second week of October. Unfortunately, every year is different so it’s hard to get it just right when planning ahead of time!

Thank you for the itinerary. It is a great start for me. I don’t have quite as much time but I hope I can get to a lot of the highlights as I’m starting from Virginia.

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Unforgettable New England road trip

• Post last modified: March 18, 2024

Planning a road trip through New England ? Get to the heart of the United States ‘ most idyllic corner with this ultimate itinerary, where soothing nature, delightful towns and proud tradition abound. Buckle up — here are all the gems you don’t want to miss.

Disclosure: All listings are independently selected. If you buy something through our links, we may earn an affiliate commission. Learn more ›

New England route

• Start: Boston
• North Conway
• North Adams
• Stockbridge
• Finish: Boston

Begin with a salty trip up along New England’s coast, where Portland, Camden and Acadia NP are highlights. While Interstate 95 is usually quicker, consider sticking to the parallel, more scenic Route 1.

Then, the character of the itinerary changes dramatically. Head west to see the White Mountains, Green Mountains and Berkshires, with the lofty scenery peaking along the iconic Kancamagus Highway.

Back on the coast, explore Mystic, Newport and Cape Cod. Home to Cape Cod National Seashore, Cape Cod provides some of America’s best beaches, making for the perfect finish to your epic drive.

Isn’t Boston the optimal starting point for you? Feel free to start the loop at the location that suits you best.

• Total distance: 1,213 mi / 1,952 km
• Total driving time: 25 h

1. Boston, MA

Massachusetts ‘ largest city, Boston is certainly a convenient place to begin a Northeast road trip. There’s the well-connected Logan Airport and an array of rental car companies to choose from.

But — most of all — Boston is a fun city to explore before you get deeper into the New England itinerary.

If one thing to do in Boston is mandatory, it’s the Freedom Trail . Walking the 2.5-mile (4 km) path, which presents top historic sites in the heart of Boston, is a one-of-a-kind activity.

After touring Boston, you don’t have to like baseball to enjoy a visit to Fenway Park. In all honesty, many visitors don’t even know the baseball rules when they enter Fenway Park for the first time.

However, baseball is an American tradition, and the Red Sox is the team in Boston. Catching a game and feeling the atmosphere at Fenway Park is a memorable experience before heading north — baseball fan or not.

More info: Where to stay in Boston

2. Portland, ME

• Driving distance:  112 mi / 180 km
• Driving time:  2 h

On Maine’s southern coast, Portland offers a lot for anyone looking for a good time.

In particular, the historic Old Port — characterized by cobblestone streets, red-brick buildings, quaint wharves and fishing piers — is the crown jewel. While its facades remind you of past glory days, the district is a modern-day gold mine with eclectic boutiques, watering holes and restaurants.

Capturing at least one of the many lighthouses in the Portland area is also a must, and especially one stands out: Portland Head Light was completed in 1791, making it Maine’s oldest lighthouse.

3. Camden, ME

• Driving distance:  81 mi / 130 km
• Driving time:  1 h 45 min

Countless scenic towns hug Route 1. Camden may be the most picturesque of them all.

Picture a small town lacing an Atlantic cove (Penobscot Bay) with steep slopes (Camden Hills). If you’re short on time, stretch your legs while you browse the stores on the timeless Main Street or sit down in the Camden Amphitheater, a small oasis facing the harbor.

With more time, hike into the rising Camden Hills State Park. But if you don’t want to work for it, you can also drive up to the top of Mount Battie, brilliantly capturing the scenery.

4. Acadia NP, ME

• Driving distance:  77 mi / 124 km

Welcome to the only national park in New England, Acadia. Calling Mount Desert Island home, it encompasses some of the Atlantic’s most untamed coastline — this is one of the most beautiful places in the US .

Although you find awe-inspiring nature all over the island, the eastern half of Mount Desert Island holds most of the park’s big-ticket spots.

An unrivaled eastern highlight is Cadillac Mountain. The views of Acadia are just spectacular from Cadillac Mountain’s summit, both the tallest point of the park and the USA’s eastern seaboard.

Cadillac Mountain peaks at sunrise and sunset but is a beautiful experience throughout the day.

On Mount Desert Island’s quieter western half, another photogenic spot not to miss is Bass Harbor Head Lighthouse. Built in 1858 on the island’s southern tip, it’s not quite as old as Portland Head Light — but no less pretty.

More info: Where to stay near Acadia NP

5. North Conway, NH (White Mountains)

• Driving distance:  212 mi / 341 km
• Driving time:  4 h 15 min

New Hampshire ‘s White Mountains region is filled with great things to do, boasting both stunning natural beauty and cozy towns to relax in.

A shining example of the latter, North Conway is the perfect White Mountains gateway when you come from the east. From here, you effortlessly reach many highlights in the dense White Mountain National Forest.

Within a few miles, Diana’s Baths Cascade — a series of waterfalls dropping 75 feet (23 m) — is a spellbinding place. Another nearby stop is Cathedral Ledge Lookout, offering White Mountains vistas destined for Instagram fame.

When traveling further west, you unlock even more of the White Mountain National Forest.

Driving the famous Kancamagus Highway — one of New England’s most scenic drives — is a jaw-dropping experience. As it runs from Conway to Lincoln, it also takes you right to your next base on the itinerary.

6. Lincoln, NH (White Mountains)

• Driving distance:  41 mi / 66 km
• Driving time:  1 h

Ready for more gorgeous terrain? At the end of the scenic Kancamagus Highway, Lincoln is a practical White Mountains gateway for highlights in the western part of White Mountain National Forest.

The Flume — a natural gorge offering a scenic pool, stunning waterfalls and, of course, mesmerizing White Mountain views — was discovered in 1808 by Jess Guernsey. She came upon it by accident while fishing in the Lincoln area.

After the finding, as the story goes, Jess first had trouble convincing her family about the discovery. It just sounded too magical to be true — but the rest is history.

Today, the Flume is a highlight in Franconia Notch State Park. You find a good variety of hiking trails in Franconia, letting you explore the White Mountains and its dense forests, stunning lakes and majestic peaks further.

7. Stowe, VT (Green Mountains)

• Driving distance:  85 mi / 137 km

A Vermont village with a postcard-worthy downtown area, Stowe sits at the foot of the Green Mountains.

Just strolling down Main Street in Stowe is an appreciated thing to do. It’s a small town, but thanks to its peaceful aura, a walk couldn’t be more rewarding.

When visiting Stove, you’re never far from fresh air and beautiful views. Stowe Recreation Path provides a convenient way to explore Stowe and the village’s lovely surroundings.

Walk, run or bike the paved trail — just be prepared that you will want to stop to take pictures.

Not in Stowe, but just a short drive away, you find the ice cream lover’s dream. Be careful so you don’t get a brain freeze at the original Ben & Jerry’s ice cream factory in Waterbury.

Extra stop: Consider stopping in Burlington, VT, a fun city on the shore of Lake Champlain. Because it’s just 36 miles (58 km) between Stowe and Burlington, you can easily include both on your New England itinerary.

8. North Adams, MA (The Berkshires)

• Driving distance:  159 mi / 256 km
• Driving time:  3 h 15 min

It’s the rolling hills and captivating culture that define The Berkshires region. Marking its northern end, where Vermont meets Massachusetts, North Adams is a great place to start exploring.

Be inspired by evocative galleries and performances at the Massachusetts Museum of Contemporary Art, set on the Hoosic River in downtown North Adams.

Or, simply cruise onwards, letting the peaceful landscape wash over you. North Adams sits along the Mohawk Trail, one of New England’s most scenic drives, finishing in nearby Williamstown.

9. Stockbridge, MA (The Berkshires)

• Driving distance:  35 mi / 56 km

America’s favorite illustrator, Norman Rockwell called Stockbridge home for 25 years. Here, with hundreds of original works, the Norman Rockwell Museum honors and showcases his legacy.

Before Rockwell, the writer Edith Wharton lived in the Berkshires, too. Visit her historic Lenox residence, the expansive Mount Home (maybe on your way from North Adams to Stockbridge), to learn and absorb the idyllic setting.

These are cultural treasures, but don’t forget that what makes the Berkshires outstanding is the mix of culture and nature.

For hiking, a beautiful spot is October Mountain State Forest . At roughly 16,500 acres, it’s Massachusetts’ largest state forest, offering both easy and strenuous trails.

More info: Where to stay in The Berkshires

10. Mystic, CT

• Driving distance:  127 mi / 204 km
• Driving time:  2 h 15 min

On the Connecticut coast, the village of Mystic peacefully sits. Get ready to discover its proud history as a waterside community and center for shipbuilding.

By the Mystic River, Mystic Seaport Museum is one of the USA’s leading maritime museums, preserving an array of seafaring artifacts. Enjoy an impressive collection covering 19 acres, with four National Historic Landmark vessels as the biggest draws.

Compact Historic Downtown Mystic has you covered for authentic shopping, diverse eateries and charming waterfront views. Especially pay attention to the Mystic River Bascule Bridge, a still-in-use drawbridge — nowadays a rare sight.

Extra stop: An alternative to Mystic or an additional stop on the itinerary is New Haven, CT, the home to the famous Yale University.

11. Newport, RI

• Driving distance:  48 mi / 77 km

The shore of Rhode Island is an essential ingredient on your New England road trip itinerary. On Aquidneck Island, Newport is an old colonial city with attractions covering a wide spectrum.

Walking the renowned Newport Cliff Walk, 3.5 miles (5.6 km) long, is a beautiful way to appreciate the Atlantic coast. Tracing Newport’s rocky coastline, it offers stunning natural scenery and fresh salty air.

As a bonus, eye-popping mansions frame the trail.

For the full experience, take a Newport Mansion tour to see how America’s wealthiest and most influential families used to live. The Breakers stands out for its extreme luxury, but the Elms and Marble House are also impressive.

More info: Accommodation in Newport, RI

12. Cape Cod, MA

• Driving distance:  120 mi / 193 km
• Driving time:  2 h 30 min

These 120 miles (193 km) take you all the way to the northern tip of Cape Cod , a peninsula separated from the mainland by the Cape Cod Canal since 1914. Be sure to make plenty of stops along the way.

Cape Cod Rail Trail, excellent for walking or biking, presents a healthy way to sightsee. Paved and extending for 25 miles (40 km) from South Yarmouth to Wellfleet, it follows the 19th-century rail lines that used to carry tourists to Cape Cod.

At the trail’s end, the landscape of Cape Cod National Seashore takes over. Hang out on the seemingly never-ending beach — seals thrive in the waters here — or hike around marshes and ponds.

The finish every peninsula should have, Race Point Beach, as far north as you get, is a phenomenal beach with huge sand dunes. On a sunny day, you might ask yourself: Is this Massachusetts or Florida?

More info: Best areas in Cape Cod

13. Boston, MA

• Driving distance:  116 mi / 187 km

It’s time to round off your unforgettable New England road trip. The last leg is the drive back to where the adventure started, Boston. From the isolated Provincetown, it’s 116 miles (187 miles) to Boston, but it’s shorter if you base yourself elsewhere on Cape Cod.

Where to stay when you road trip through New England

New England takes pride in its atmospheric, often historic inns. Consider making your road trip even better by booking one of our favorite places to stay on Cape Cod.

Appreciate the English Country style at the Old Harbor Inn , a luxurious bed and breakfast set in Chatham. Each of the twelve rooms is unique and the location spot-on for day trips across Cape Cod.

Or, stretch your budget by staying at the Breakwater Hotel , slightly outside Provincetown, at Cape Cod’s northern tip. Drive 5 minutes or walk 30 minutes to get to Provincetown’s heart.

New England itineraries with days

For the full New England road trip, we recommend allowing at least 3 weeks. If you have less time, it’s a good idea to break up the itinerary to focus on your favorite parts.

Ultimate itinerary (3 weeks)

• Day 1-3: Boston (2 nights)
• Day 3-5: Portland (2 nights)
• Day 5-8: Acadia NP (3 nights)
• Day 8-10: North Conway (2 nights)
• Day 10-12: Lincoln (2 nights)
• Day 12-14: Stowe (2 nights)
• Day 14-15: The Berkshires (1 night)
• Day 15-16: Mystic (1 night)
• Day 16-18: Newport (2 nights)
• Day 18-21: Cape Cod (3 nights)

2 week road trip (Atlantic coast)

• Day 1-2: Mystic (1 night)
• Day 2-4: Newport (2 nights)
• Day 4-7: Cape Cod (3 nights)
• Day 7-9: Boston (2 nights)
• Day 9-11: Portland (2 nights)
• Day 11-14: Acadia NP (3 nights)

7 day road trip (Mountain trip)

• Day 1-4: White Mountains (3 nights)
• Day 4-6: Green Mountains (2 nights)
• Day 6-7: The Berkshires (1 night)

New England road trip FAQ

This ultimate New England road trip is 1,213 miles (1,952 km) long, taking 25 hours excluding the time you need for the stops along the way.

The journey includes six states: Massachusetts, Maine, New Hampshire, Vermont, Connecticut and Rhode Island.

The main stops on the itinerary are Boston, Portland, Acadia NP, White Mountains, Green Mountains, The Berkshires, Mystic, Newport and Cape Cod.

For the full loop, we recommend allowing 3 weeks or more. But you can break the itinerary up and enjoy a shorter journey, too, for example, focusing on the coast or the mountains.

With 7 days, it’s as good idea to concentrate on a certain area. To see both a lively city and New England’s timeless coastal environment, a popular combo is Boston and Cape Cod.

More New England guides

• Cape Cod vacation guide
• Where to stay in Cape Cod
• Lodging near Acadia NP
• New England bucket list

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7 Day New England Road Trip Itinerary: The Perfect Fall Getaway

This post may contain affiliate links, meaning if you buy or book through one of these links, I may earn a small commission .

Have you been dreaming of witch trials sites, fiery maple trees, and scenic rural drives? For fall lovers, one week exploring the vibrant foliage of New England is the ultimate bucket list experience. An adorer of autumn myself, I wrote the perfect 7 day New England road trip itinerary to fulfill your leaf peeping dreams.

This itinerary is inspired by my own road trip through New England last year, which included New Hampshire, Vermont, and Massachusetts. Although my home state of Ohio has gorgeous falls too and I’d already seen Massachusetts at peak coziness, I yearned to more deeply explore the hilly forests and farmland of the Northeastern United States. Sneaking in a lobster roll or two while revisiting Massachusetts wouldn’t hurt either!

New England’s compactness makes it easy navigate, while offering charming small towns, rewarding hiking trails, and coastal views. As this road trip covers three states, I’ve carefully planned this itinerary for the most efficient New England sightseeing route. Are you ready to get witchy in Salem, MA and cozy in Woodstock, VT? Let’s get into it.

Ultimate 7 Day New England Road Trip Itinerary

I have mapped out the below itinerary to further ease your navigation between these amazing New England destinations.

Related: 61 Awesome Bucket List Ideas for Your Best Fall Ever

Day 1: Massachusetts – Arrive Into Boston

This 7 day New England road trip itinerary kicks off in Boston, whose urban streets transform under autumn’s spell, particularly in the Beacon Hill neighborhood. If you are flying, you’ll land at Boston Logan International Airport, so grab a 10-minute Uber/Lyft into the city. Arriving either in the morning or the night before allows you to have a full day of sightseeing what they call “Beantown” .

The best thing to do during one day in Boston is to follow the Freedom Trail past sites significant to Boston’s Revolutionary War history. Either join a guided tour or simply follow the red line on the pavement from Boston Common. This self-guided app also provides an informative tour at your own pace.

Afterwards, stroll the boutiques and cobblestone streets of Beacon Hill or consume seasonal treats on the Underground Donut Tour .

Finish by dining at one of many Italian restaurants in Boston’s North End before turning in for the night. Don’t forget to stop in for a cannoli at Modern Pastry or a Boston cream donut at Bova .

Craving a spooky experience, but tired of walking? Take this Boston Ghosts and Gravestones Trolley Tour .

Suggested Stay: Courtyard by Marriott Boston Downtown/North Station

Day 2: Massachusetts – Salem, MA

No single 7 day New England itinerary would be complete without a visit to the Witch City, or Salem, MA, where the infamous 1692 witch trials took place. To make the 45-minute drive from Boston, pick up your rental car the morning of day two (we rented ours at the airport).

Note: If visiting during the super busy month of October, get into Salem by 9am to ensure you find parking and avoid traffic jams. An alternative is to stay in Boston for one more night and take a 30-minute train or ferry into Salem . I recommend booking a room at Courtyard by Marriott Boston Downtown/North Station to be close to both the train and Freedom Trail.

Here is the best way to spend one day (also consider following my Salem day trip itinerary ):

• Visit the Salem Witch Museum (purchase a timed entry ticket online)
• Stop into the Salem Witch House
• Stroll past the wand shops, fortune tellers, and apothecaries of Essex Street
• Take a spooky witch trials walking tour

For a nice dinner with lots of ambiance, dine at Ledger Restaurant . For less fuss and laid-back vibes, get a lobster roll and beer at The Lobster Shanty ; they serve delicious clam chowder too!

Suggested Stay: In Salem at the Hampton Inn Salem Boston or in Boston at the Courtyard by Marriott Boston Downtown/North Station

Related: 13 Best Things To Do In Salem , MA In October

Day 3: New Hampshire – Artist Bluff Trail

It’s time to get out of the city and into the White Mountains of New Hampshire, which deliver sweeping views over fall’s colorful tree canopies. On the morning of day three, depart from Massachusetts and drive about two hours north to Lincoln, New Hampshire. While there are plenty of hotels in and around Lincoln, you may opt to stay in a cozy cabin instead.

Recommended Hotel: Holiday Inn Express & Suites Lincoln East – White Mountains

You can find cabins all around the area, so I recommend doing a search on Airbnb and seeing what’s available during your travel dates. My husband and I stayed in this adorable dog friendly cabin in Wentworth, New Hampshire last year, where the stargazing looked like a sheet of glitter over the sky.

After settling in, it’s time for your first hike of the trip: the 1.5-mile Artist Bluff Trail in Franconia State Park. This steep loop trail leads to panoramic views over the fiery-colored treetops framing Echo Lake. For less climbing, take the Cannon Mountain Aerial Tramway just one mile away, which lifts you 4,080 feet to the peak of Cannon Mountain.

If you still have time and energy, also consider hiking the gorgeous two-mile Flume Gorge loop trail , which follows along an 800-foot natural gorge at the base of Mount Liberty. Just remember this trail has an entry fee of $18 online ( book here ) and $21 at the trailhead.

After hiking, visit a local brewery, like Rek-Lis Brewing Company , for dinner and drinks. As we were staying closer to Plymouth, NH, we stopped into Sole Track Brewing to share a tasting paddle. For dinner, we grabbed burgers at The Last Chair , a ski-themed brewery that had tasty burgers and peanut butter porter.

Day 4: New Hampshire – Kancamagus Highway

The next day in New Hampshire, you will experience the state’s most iconic leaf peeping adventure: the Kancamagus Highway . This 34.5-mile stretch of roadway between the towns of Lincoln and Conway leads past beautiful mountainscapes and other gorgeous natural scenery.

Keep in mind there are no gas stations along this route, so fill up before heading out. Also, you must pay $5 per day to park in White Mountain National Forest . You can simply put the cash or check in an envelope to leave at a drop box at the first stop along the highway.

Don’t be afraid to pull over frequently along the Kancamagus Highway. Otherwise, this enchanting stretch only takes about one hour to complete without stops.

Here are the must-see sights along the Kancamagus Highway, in order heading east:

• Otter Rocks
• Hancock Overlook
• Panoramic Overlooks
• Pemigewasset Overlook
• CL Graham Wangan Overlook
• Sugar Hill Scenic Vista
• Sabbaday Falls: Most popular hike along the way, only .5 mile trail that leads to a waterfall
• Russell-Colbath House
• Campney Fall: 3.1 miles out and back, .6 miles additional miles to reach the summit of Mount Chocorua, which has gorgeous 360-degree views
• Rocky Gorge: lovely in fall and nice place to picnic
• Lower Falls: this super short hike to a waterfall is the most popular stop of the drive
• Albany Covered Bridge

Stay overnight near Lincoln, NH again. If you are staying in a cabin, consider having a cookout or bonfire to make s’mores!

Otherwise, dine out at Moat Mountain Smokehouse and Brewery in North Conway before turning back to drive the Kancamagus Highway in reverse. You could also visit Woodstock Inn Brewery in North Woodstock upon completion of the drive.

Day 5: Vermont – Woodstock

The next morning, it’s time for the last leg of your trip: the friendly small towns of Vermont where even the automated speed signs scold you politely.

The drive to charming Woodstock (the one in Vermont, not New Hampshire) will only take about and hour and a half from Lincoln, NH. You could stay in a hotel in Woodstock or simply book an Airbnb in the surrounding area (we loved this adorable hobby farm ).

Recommended Hotel: The Village Inn of Woodstock

This route around Woodstock will be the delight of any 7 day New England road trip itinerary:

• Quechee Gorge: Visible from an overpass along Route 4, this 165-feet gorge (Vermont’s deepest) was formed by glaciers 13,000 year ago. You can park in a lot off Route 4 to quickly view the gorge or hike the Quechee Gorge Trail at Quechee State Park .
• The Skinny Pancake : A great breakfast/brunch stop in Quechee. I loved my savory crepe with apple, brie cheese, and a locally sourced blueberry compote.
• Woodstock: Explore the antique shops, cafes, and lovely covered bridges of this charming small town. Don’t forget that all parking is paid – even along the street!
• Billings Farm and Museum : For $17 you can explore the grounds and stables of this working farm tucked among the rolling hills. I purchased a small apple cider to sip as I strolled past dairy calls being milked, goats perched on top of fences, and horses grazing. Check their calendar for daily events.
• Woodstock Farmers Market: The perfect stop for locally produced products, like cheese and maple syrup.
• President Calvin Coolidge Historic Site : The site of several preserved buildings from Calvin Coolidge’s childhood home at Plymouth Notch, including his family homestead. Also see where the 30th president of the United States attended church, his father’s store, the post office, and Coolidge’s summer white house office inside of a dance hall.

Make a reservation to dine in downtown Woodstock at The Prince & The Pauper Restaurant or Santé .

Travel Savvy Tip

With the rise of social media, certain farms around the Woodstock area have become popular photo spots for Instagrammers. Sadly, this has escalated into a problem for local residents, with visitors clogging roads and trespassing onto private property.

Local governments have begun taking action, closing roads leading to Jenne Farm and Sleepy Hollow Farm during the month of October. Please respect these rules – there are plenty of other gorgeous locations all around Vermont to photograph!

Day 6: Vermont – Grafton

To get a true small town Vermont experience, drive one hour south of Woodstock to the tidy little village of Grafton. Grafton is especially pleasing during peak foliage season, when bright shades of red, orange, and yellow frame tall white church steeples and local shops.

However, don’t confuse Grafton’s impressive collection of well-preserved historic buildings for an open-air museum. This is a functioning, tight-knit community that still holds Gilmore-Girls-style town meetings to this day.

Just be sure to download any maps before heading out, as I found the town’s cell service to be weak to nonexistent.

Here are the best points of interest to check out in Grafton’s quaint and walkable town center:

• Learn about making maple syrup at Plummer’s Sugar House before buying some to take home with you.
• Hike a trail at the Grafton Trails & Outdoor Center . Grafton also has a cute welcome sign a bit further south down Grafton Road.
• Journey to the past at the Grafton Historical Society.
• Sample local cheese varieties at the Grafton Village Cheese Company .
• Browse locally produced gifts and home goods at Mercantile and adjacent Dover House Antiques.
• Wander into the Turner Hill Interpretive Center to learn the story of Alec Turner, who settled in Grafton and to raise his family after escaping slavery.
• Check out the Nature Museum to learn about native New England flora and fauna and wander down various nature trails.
• Discover unique copper sculptures honoring Northeastern Native Americans at Jud Hartman Gallery .

If you get hungry, the Grafton Village Store has you covered for coffee, pastries, and simple meals. For a sit-down dinner, book a reservation at the rustic Phelps Barn Pub or the cozier 1801 Tavern at The Grafton Inn .

Day 7: Complete Your New England Road Trip Itinerary at Boston Logan Airport

Just as the leaves must eventually fall to the ground, this New England road trip itinerary must reach its end too. Hopefully you had the fall foliage experience you’ve been dreaming about and are already planning your return trip!

If you drove from your house, then it’s time to make the trek back home. Otherwise, the drive from Woodstock, Vermont to Boston Logon International Airport will take about two and a half hours. I recommend arriving two to three hours before your flight to have time to drop off your rental car, check any bags, and find your gate.

Is Your New England Road Trip Itinerary Longer Than 7 Days?

There are so many options for New England itinerary add-on’s:

• Consider spending one extra day in Boston.
• Stay in Salem, MA for two days and day trip to nearby Danvers (formerly Salem Village) to see even more witch trials sites!
• Explore additional charming towns along the Vermont and New Hampshire border, including White River Junction, Windsor, Hanover, and Battlebro.
• Add an extra day to New Hampshire to take advantage of countless more hiking trails.
• Add an additional state: Maine! Explore trendy Portland, eat lobster rolls in Bar Harbor, or go hiking at Acadia National Park .

There you have it – the recipe for a dreamy and memorable 7 day road trip itinerary through New England. It’s the best combination of the bustling Atlantic coast of Massachusetts, the mountains of New Hampshire, and the farms of Vermont. You’ll see exactly why New England is beloved by leaf peepers, maple syrup addicts, and outdoor lovers alike!

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10 day New England Road Trip Itinerary (Portland to Boston Drive)

Looking to spend some time on the east coast by taking a road trip through new england this road trip itinerary will take you through some of america’s oldest cities and towns..

Get ready to be blown away by idyllic small-town vibes, white steeples with brick-red facades, fresh lobster rolls, whale watching, and history upon history on this New England road trip!

This New England road trip will take you from Portland, Maine up to Acadia National Park, then back down through Portsmouth and into Boston, Massachusetts.

🚗 When booking your New England Road Trip car rental online, I recommend using Discover Cars . They provide the best deals for car rentals in New England!

Prepare for yourself for this New England road trip by making sure you have all the gear you need to make the best of your time in the car!

Let’s jump in!

Quick Overview of the New England Road Trip Itinerary

Boston to portland maine map.

A quick summary of stops on your 10 Day New England Road Trip Itinerary

• Days 1-3: Portland, Maine (3-hour drive time on day 3)
• Days 3-5: Acadia National Park, Bar Harbor (4-6 hour drive time on day 5)
• Days 5-10: Portsmouth, New Hampshire, and Boston, Massachusetts
• Airports: Portland International Jetport in Portland, Maine (PWM); Logan International in Boston, Massachusetts (BOS)
• Transit: Rent a car for pick up at PMW and drop off at BOS

New England Road Trip Itinerary

The new england road trip itinerary days 1-3: portland, maine.

• Land at Portland International Jetport early in the day if possible and pick up your rental car
• You’ll want to book your stay for 2 nights in Portland

Where to Stay in Portland, Maine

The best accommodation option would be to stay in or very close to Old Port. This is the historic downtown area of Portland with many cute boutiques for shopping and restaurants within walking distance.

If the prices in this area are out of your budget, I would recommend staying at an accommodation in either Portland’s East End or West End as they are both near the heart of Portland, Old Port.

• The Portland Harbor Hotel | cute boutique style
• The Press Hotel | sleek and upscale style
• The Courtyard by Marriott Downtown/Waterfront | cost-effective option near all the fun sites

Day 1: Landing in Portland, Head Light, and Old Port

• Today you’ll see some great highlights of Portland including the lighthouse and Old Port
• Portland city drive time: 15-30 minutes around town, including the airport to Old Port

Start your morning off with breakfast at Becky’s in the West End. The blueberry pancakes are DELISH, however, the omelets are also great for a high-protein meal.

• Becky’s Diner | Address: 390 Commercial St, Portland, ME 04101

After breakfast, head over to Portland Head Light State Park for a short hike! This is one of the most popular sites in Maine and offers incredible views out over Casco Bay.

You can even do a lunch picnic here! Wear walking shoes (or sandals if you’d like to hike down to the water) and do some rock climbing to get some beautiful pictures of the Portland Headlight.

Spend as much time as you want here–it’s so beautiful! (We came here twice!)

Pro-tip: Tie up your hair and bring a jacket as it’s pretty breezy and a little chilly here!

• Portland Head Light State Park | Address: 1000 Shore Rd, Cape Elizabeth, ME 04107

In the afternoon, take an hour-long tour of the Wadsworth-Longfellow House which was Maine’s first house museum that opened up to the public. Longfellow was a national literary man of his time and most furnishings in his house are original or belonged to his family.

• Wadsworth-Longfellow Museum | Address: 489 Congress St, Portland, ME 04101

After getting your history fix, you can take a walk and explore Old Port. This area has many cute boutiques and fun restaurants to try out!

Stop by The Holy Donut for a delicious snack (even multiple times over a 2-day trip) with interesting flavors such as the Maine blueberry cake donuts or chocolate sea salt flavor.

• The Holy Donut | Address: 177 Commercial St, Portland, ME 04101

There are also so many restaurants lined up here that you can grab a quick lunch before doing all your shopping. Some recommendations include Duckfat (amazing Belgian-style fries with sauces) and The Honey Paw (ramen noodles and Asian infusion).

Or head over to the Maine Lobster Shack for a delicious lobster roll–nothing is better than this fresh-caught lobster. You can’t go wrong with the Maine Lobster Roll or the Brown Butter Lobster Roll, and try the Maine Root Soda while you’re here.

• Maine Lobster Shack | Address: 425 Fore St, Portland, ME 04101

Day 2: More of Historical Portland and Peak’s Island

• Today you’ll get some more historical experiences of Portland and explore Peak’s Island by ferry
• Portland city drive time: 10-15 minutes around town

The next morning, grab some breakfast at the Bayside American Cafe. With their delicious menu, you can’t go wrong – everything from Maine blueberry pancakes to Bayside eggs benedict!

• Bayside American Cafe | Address: 98 Portland St Portland ME 04101

After breakfast, check out another museum for the history buff: reserve a ticket to spend about an hour touring Victoria Mansion, a historical landmark that is one of the oldest in the country and known for its architecture and original interior design.

• Victoria Mansion | Address : 109 Danforth St, Portland, ME 04101

After touring the mansion, grab lunch at Hot Suppa! This Southern diner (and what I would consider hipster) has delicious offerings such as the Mother Clucker.

• Hot Suppa | Address: 703 Congress St, Portland, ME 04012

After getting a good bite in, take a 17-minute ferry to Peaks Island for some more exploring; we spent half a day here and had so much fun!

As you get off the ferry, rent a little golf cart From Mike’s Carts to get around the area. You can grab Lisa’s famous cinnamon bun at Peak’s Café as you start your cart tour.

Use this map to help you navigate your way around Peak’s Island. Head north first so that you can end your drive on Seashore Avenue, which provides endless views of the ocean.

Partway through your drive on Seashore Avenue, you can park your cart along the road and take a short hike to Battery Steele, which used to be a military fortification now graffiti-covered.

If you have time, you can also drive around the neighborhood and check out some of the cutest coastal homes–make it a game to find the best-named house!

You can also check out the Fifth Main Museum on the island as well to learn more about the history of the Civil war and other exhibits.

Keep track of the ferry schedule so you don’t miss the last one! Before you go, grab an ice cream cone from Down Front, a small convenience store.

• Ferry to Peak’s Island | Address : 56 Commercial Street, Portland, Maine 04101

Day 3: Close Out Your Portland Itinerary and Drive 3 Hours Toward Acadia

• Today you can choose your morning experience and then prepare for your drive to Bar Harbor
• Portland to Bar Harbor drive time: 3 hours

You can pack everything the night before and check out as you leave in the morning. Start off the day by heading back to Old Port to grab some snacks and breakfast in preparation to drive out.

Since you’ll be savoring your last moments in Portland, Maine, you can choose what you’d like to do:

• last-minute souvenir shopping in Old Port
• taking some last looks at Portland Headlight
• check out the Portland Museum of Art

You will want to leave Portland by 1 PM.

• Portland Museum of Art | Address: 7 Congress Sq, Portland, ME 04101

That’s everything for your 3 day Portland itinerary ! It’s about a 3-hour drive west to your next stop so you’ll want to have all your favorites (snacks, music, and conversation topics) ready to go!

The New England Road Trip Itinerary Days 3-4: Acadia National Park and Bar Harbor

• When you arrive in Bar Harbor, check into your hotel and get some dinner in town
• You’ll want to book a 2-night stay in Bar Harbor

Where to Stay in Bar Harbor

For accommodations, stay directly in Bar Harbor at a cute inn to get the best of your time. Keep in mind that cell service around these parts is spotty at best, so don’t be afraid to stop and ask for directions!

• The Inn on Mount Desert | affordable stay in Bar Harbor
• The Elmhurst Inn | old-fashion boutique style in Bar Harbor
• Acadia Hotel – Downtown | upscale stay in Bar Harbor

Day 3 Continued: Getting to Bar Harbor and Settling In

• Spend your time strolling through this charming small town
• Portland to Bar Harbor drive time: 3 – 3.5 hours

Continue your New England road trip itinerary and head west towards Bar Harbor, where Acadia National Park Pond is located. You should arrive in the afternoon and get lots of views of lakes and beautiful nature scenes.

Since you’ll be here later in the afternoon, head into Bar Harbor which offers a small-town feel and is a fantastic place to enjoy some delicious food.

We got ice cream cones every time we went (which was only twice!). While you’re at it, make sure to buy some snacks, maybe even a sandwich lunch to enjoy while in Acadia National Park Pond the next day.

This would be the time to grab souvenirs or do some window shopping in Bar Harbor. There are so many cute boutique shops to just browse through!

For lunner (lunch + dinner), Galyn’s is a cozy little seafood restaurant in a Victorian-era house that has options for outdoor seating.

Opt to sit out on the patio and enjoy the fresh air and views while you eat your clam chowder soup. If that’s not for you, they also have small plates, fettuccine, sandwiches, and many more options to choose from. It was wonderful!

• Galyn’s | Address : 17 Main St, Bar Harbor, ME

Day 4: Explore Acadia National Park Pond

• Get an early start at Acadia National Park and do all the exploring on the hiking trails and beaches
• Bar Harbor to Acadia drive time: 15 – 30 minutes going through the park

Continue your New England road trip and get an early start to Acadia National Park Pond, which is known as the “Crown Jewel of the Atlantic Seaboard” and it’s easy to see why.

Take your time in Acadia and explore all that it has to offer, you won’t be disappointed! The mountain views are incredible, the road is scenic and well-maintained.

The weather in Acadia is usually pretty nice, but it can get chilly in the evenings. Make sure to pack layers so you’re prepared for everything! I had a light jacket with me, but by midday, I was getting pretty warm from the sunshine and hiking.

One of my favorite hikes here is the Beehive Loop , which is a great way to get acquainted with the difficult trails.

If you are looking for an adventurous hike, this 450-foot cliff trail will get your heart pumping! As one of Acadia’s most popular hikes, expect steep granite staircases that challenge even experienced backpackers (think ladders and iron rungs), as well as exposed cliffs. The trail is about 1.4 miles roundtrip and can take anywhere from 1-3 hours.

Another more moderate hike is the Bubble Trail which branches into North and South.

Both trails are reasonable, but if you’re looking for a shorter trail, take the Bubble Rock trail to see “the bubble,” which is a huge rock shaped like a bubble sitting precariously on the cliff of the mountains.

If mountains aren’t your thing and you’re more of a beach lover, Sand Beach and Echo Lake Beach are great for swimming and hanging out. You’ll most likely come across Sand Beach first if you’re coming from the entrance at Bar Harbor, which will also bring you to the trailhead of the Beehive Loop.

At the beach, you can unpack your lunch and enjoy a nice view out into the ocean with the sun keeping you warm.

However, if you are hungry after your hiking expedition, enjoy lunch at Jordan Pond House where you can dine on traditional meals of New England that include lobster rolls, chowder, and more.

A popular fare here is popovers and tea and if you are like me who had no idea what a popover is… it’s a light roll made of egg batter and can be eaten with whipped cream or jam and tea. Delish!

• Jordan Pond House | Address : 2928 Park Loop Rd, Seal Harbor, ME 04675

For more adventuring in Acadia, make the drive to Cadillac Mountain or Thunder Hole. Cadillac Mountain is the tallest mountain on the East Coast at just over 1,500 feet with unparalleled views over Frenchman Bay and beyond.

Finally, no road trip to Acadia National Park is complete without a stop at the famous Thunder Hole! Don’t forget your raincoat because it looks like thunder when waves crash into rocks down below, causing an amazing sound experience for visitors nearby.

After a long day exploring Acadia National Park head back towards Bar Harbor at night to enjoy dinner in town. Grab a seat at one of my favorite restaurants, the family-owned Side Street Cafe.

The staff is so welcoming and the restaurant really fosters an atmosphere of community. Everything here is amazing–from appetizers to sandwiches and burgers.

• Side Street Cafe | Address: 49 Rodick St, Bar Harbor, ME 04609

After all the energy spent at Acadia, get some much-needed rest before the long 5.5-hour drive to Boston!

The New England Road Trip Itinerary Days 5-10: Boston, Massachusetts (with a stop in Portsmouth)

Where to stay in boston.

Driving around Boston can get congested during peak traffic hours, which will make your trip take longer than expected if you don’t plan accordingly.

Because of that, we decided to stay outside of Boston proper. Our Airbnb was about a 30-minute drive to Boston, which was actually more cost-effective for us since we weren’t always going to be in Boston proper.

If you would prefer to stay in Boston, you may be able to save on driving time on congested roads.

• Hampton Inn Boston Logan Airport | 16-minute drive to Boston, typical hotel stay
• The Newbury Boston | 3-minute walk to Boston proper, upscale stay

Day 5: Make the 5.5-hour drive South to Boston, with a short stop in Portsmouth, NH

• Check out of your rooms and prepare for a long drive south to Boston
• You’ll want to book your rooms in Boston for 5 nights
• Bar Harbor to Bass Harbor Light Station Drive time: 30 minutes
• Bar Harbor to Portsmouth Drive time: 3 hours, 55 minutes
• You’ll make a lunch stop in Portsmouth and get the chance to explore for a short while
• Portsmouth to Boston drive time: 1 hour

As you continue your New England road trip itinerary and start your drive down to Boston, you can make a stop at Bass Harbor Light Station. This historic lighthouse is off the beaten path but definitely worth checking out if you would like to add another lighthouse to your list!

After taking some pictures of the lighthouse, continue on your New England road trip and make a stop in Portsmouth, New Hampshire.

With a population of approximately 21,000 people, Portsmouth is the 13th largest city in all of New England! It’s also home to the Strawberry Banke Museum which consists of 11 historic homes and buildings dating back as early as 1695.

You can grab lunch in Portsmouth from places like the Clipper Tavern, The Wilder, or The Franklin.

If you’re game for ice cream (which is always on my list), check out Annabelle’s Natural Ice Cream, made with only the best ingredients! Then take a walk down the main street and explore the town on foot.

• Annabelle’s Natural Ice Cream | Address: 49 Ceres Street, Portsmouth

You’ll see an iconic New England church and steeple right in the town center. Right along this street are some cool shops like the River Run Bookstore, a fun game store called Diversions and Games, and a cute international boutique shop, Ten Thousand Villages.

After walking through some shops and exploring a little in Portsmouth, hop back in the car and finish out your New England road trip in Boston!

Next up on your New England road trip: Boston!

Day 6: Walk the Freedom Trail

• You’ll explore the freedom trail on foot and really get to see all the history in Boston proper – prepare yourself, it’s a long day of walking!
• Boston city drive time: 15-30 minutes depending on your stay

Take the rest of the days and go at your own pace. In this section of the New England road trip, you will not be driving across state lines or going long distances anymore.

There is SO much to see that you’ll need to make your itinerary work for you! Consider your top historic sites and your level of energy for all the walking you might do in the city. With that said, let’s jump into exploring Boston!

Boston is home to so much history! On the top of your list to do in Boston, the Freedom Trail .

This trail is a must-see for anyone who visits the city! The Freedom Trail is a self-guided historic walking trail that leads you to 16 of Boston’s most iconic landmarks. It is 3 miles long and will take you a whole day to complete as you make stops along the way.

You’ll want to get started on the Freedom Trail in the Boston Commons (1) . From here, you can visit the information center to get yourself a map and ask any questions. You’ll know you’re on the trail by following the marked trail embedded in the sidewalk.

As you get started, you’ll see the Massachusetts State House (2) located on a hill, and following that will be Park Street Church (3) , which was one of the first landmarks travelers would see coming into Boston.

Next, you’ll come upon the Granary Burial Ground (4) , which has some of the most influential historic persons like Benjamin Franklin’s parents, Paul Revere, and John Hancock. After this you’ll come upon a small square where you can visit King’s Chapel & King’s Chapel Burying Ground (5) , which is America’s oldest running pulpit – the bell still rings to call worshippers into the church.

You’ll also see Benjamin Franklin’s statue (6), the Old Corner Bookstore (7), and the Old South Meeting House (8) where the Boston Tea Party began!

At this point, you are right in the middle of a commercial hub to grab lunch – we got the familiar and ordered a burrito at Chipotle. However, there are so many restaurants to choose from.

Continue your trek on the Freedom Trail after lunch to the Old State House (9) , which is Boston’s oldest standing public building.

The trail will then take you to the site of the Boston Massacre (10) of 1770 where the Redcoats and Boston civilians broke out in gunfire. You’ll see the site marked with a marker.

Next up is Faneuil Hall (11), the “home of free speech” and “cradle of liberty,” you’ll see the popular golden cricket weather vane. It is now a cool marketplace and is one of Boston’s most popular attractions!

There is something for everyone with its many shops, restaurants, and music venues all in an old-fashioned market atmosphere. Right outside the marketplace, you might spot jugglers and dancers giving a great show!

After a little shopping, you’ll continue walking towards Paul Revere’s home (12) where you can take a tour inside. Continue your trek on the Freedom Trail to the Old North Church (13) , where you’ll see a statue of Paul Revere – this was the site of his midnight run.

You can also grab a snack in this area at Mike’s Pastries as he has some of the most delicious cannolis (address mentioned below)!

After the Old North Church, you’ll come to Copp’s Hill Burying Ground (14) , which is the final resting place for many artisans and craftsmen in the North End of Boston.

You’ll then take a 20-minute walk towards the USS Constitution (15) , which is the oldest commissioned warship afloat that fought during the war of 1812. Today, it is managed by the US Navy. You can purchase tickets and actually walk on the ship and even go underdeck to see the cannons and rooms.

Finally, head towards the last site of the Freedom Trail, Bunker Hill Monument (16) , which is a 221-foot granite obelisk.

At this point, it is likely that you’re well into the afternoon so I would recommend booking an Uber to drive you back to the Boston Commons, which is most likely where your car is parked.

If you would rather continue walking, you could walk the 3 miles back toward the commons.

From here, you can choose a place to grab dinner and call it a night! You’ll be exhausted from all the walking and sightseeing you’ve just completed.

Day 7: Whale watching, Boston Harbor, and the North End

• After all the walking yesterday, take it easy and go whale watching
• Explore the Italian district of the North End

Boston is the perfect place for whale watching ! There are several tour companies along the water where you can book a trip to see the whales.

The best time to see the whales in Boston is during the months of May – October when the whales migrate during the warmer temperatures.

Book your Boston whale-watching tour!

Boston Harbor Cruises has experienced marine biologists and tour guides to give you information while you are on the cruise. They are also experts in knowing the best spots where whales like to hang out.

You’ll head to Long Wharf, which is near the New England Aquarium to get in line for the tour. On our whale-watching expedition, we went to Stellwagen Bank National Marine Sanctuary.

It took a few minutes of watching, but we did spot some whales!

A whale-watching tour can take anywhere from 3-4 hours. Wear a jacket as it will get cold when you’re in the middle of the ocean.

• New England Aquarium | Address: 1 Central Wharf, Boston, MA 02110

After your tour, you’ll be right in the Boston Harbor. From here, you can walk along the waterfront and explore some sites. You can relax at the Charles River Esplanade which is a walking path along the waterfront with plenty of benches.

If you would like some more Boston history, check out some of the museums such as the Museum of Science, the Boston’s Children Museum, or the Boston Tea Party Ships and Museum.

For dinner, head to the Italian quarter in the North End which is the oldest neighborhood in Boston and has some of the most delicious food.

If you’re not into Italian food then there is still plenty of great places to try out including sushi, burgers, or lobster rolls that are sure to please everyone in your road trip group!

For dessert, try out the cannolis at Mike’s Pastry as they have been making these delicious pastries since 1926. The lines can look intimidating as they go out the door, but it goes quickly and the staff is very aware of your status in line.

• Mike’s Pastry | Address: 300 Hanover St, Boston, MA 02113

Day 8: Harvard University and Candle Pin Bowling

• Explore the college town of Harvard University
• Have fun candlepin bowling
• Boston to Cambridge drive time: 30 minutes – 1 hour depending on your stay

Boston is also home to many amazing colleges and universities. On this day of the New England road trip, we chose to take a visit to Harvard.

Start off by grabbing brunch at Le’s Vietnamese restaurant then check out the historic Harvard Bookstore.

After this, we wanted to take a walk around the Harvard Campus. Do note that visitors aren’t allowed within the buildings without a guest pass.

We just walked around the campus and noted the buildings as well as the plaques that were displayed. It was pretty cool to say that we went to Harvard!

If you’d like to experience Harvard University more deeply, you can book a 70-minute student-led tour to see everything the university has to offer. Either way, you’ll want to make sure that you don’t miss out on visiting Harvard Yard.

There are also three art museums and the Harvard Museum of Natural History to explore.

Book your Harvard Walking Tour

For a more relaxed New England activity, go candlepin bowling at Sacco’s bowling alley in Sommerville, which is about a 10-minute drive from Harvard University.

This type of bowling is a little different than what you might be used to. Candlepin bowling is played with smaller balls and the pins are thinner as well; it tends to result in more strikes which means more points!

Sacco’s does offer food for purchase so we ordered flatbreads off their menu for dinner.

• Sacco’s Bowling Haven | Address: 45 Day St, Somerville, MA 02144

Day 9: Fenway Park, New England Holocaust Memorial, Boston Public Market, Cheers, and a Ghost Tour

• Revisit Boston proper: there is so much more to see that might have been missed on the Freedom Trail – take your last day to visit all those last sites
• Boston city drive time: 15-30 minutes depending on where you stay

I’m not much of a sports fan, but I really enjoyed a walk around Fenway Park where the Red Sox play.

It was built back in 1912 and has been around ever since, also displaying members of the team around the stadium. With a guided tour, you’ll be able to visit the stadium’s collections of photographs, artifacts, and more!

Boston also has a memorial for the persecuted Jews during the Nazi regime where you can visit the New England Holocaust Memorial.

After walking through the memorial, you’ll end up near the Boston Public Market, which is filled with produce and gourmet food. This is the perfect spot to grab lunch!

• New England Holocaust Memorial | Address: 98 Union St, Boston, MA 02129
• Boston Public Market | Address: 100 Hanover St, Boston, MA 02108

If you’re a huge literary fan, you can visit the Edgar Allan Poe statue, which is so descriptive and very well-made. You can see one of his most notable works: The Tell-Tale Heart. The statue stands right across the street from the Boston Commons south of Boyleston Street.

Another iconic stop in Boston is to visit the Cheers restaurant filled with memorabilia from the show! It’s located on the other side of the Boston Commons where Edgar stands. You can grab dinner here and reminisce about the show.

• Cheers restaurant | Address: 84 Beacon St., Boston, MA 02108

For the brave, book a trolley ghost tour to hear bout Boston’s most haunted locations! The tour guides are historians, so you can be sure that the stories they tell will be accurate and interesting-we learned so much about the cemeteries and ghost sightings!

Fun fact: there’s a little girl who is regularly spotted right next to these gravestones!

Side Note: You can also spend one night in a historic hotel or B&B. Some of these places date back to the 1800s! Most hotels even offer their own ghost tours if you’re feeling brave enough to stay overnight at one of their historical spots.

As you hang out later in Boston, you can see the Massachusetts State House beautifully lit up in the night sky! You can grab dinner to go and have a picnic in the Boston Commons, which is a huge park area.

Day 10: Check out and return home

• Boston to Logan Airport drive time: 15-30 minutes depending on your stay

After exploring all you can in Boston, it’ll be time to head back home. Return your car to Logan International Airport and from there fly out to your home airport.

Summary of the 10 Day New England Road Trip Itinerary

• Breakfast at Becky’s Diner | Address: 390 Commercial St, Portland, ME 04101
• Explore Portland Headlight | Address: 1000 Shore Rd, Cape Elizabeth, ME 04107
• Get your history in at Wadsworth Longfellow’s place | Address: 489 Congress St, Portland, ME 04101
• Shop in Old Port and get a snack at the Holy Donut | Address: 177 Commercial St, Portland, ME 04101
• Grab food at the Maine Lobster Shack | Address: 425 Fore St, Portland, ME 04101
• Breakfast at Bayside American Cafe | Address: 98 Portland St Portland ME 04101
• Check out more history at the Victoria Mansion | Address : 109 Danforth St, Portland, ME 04101
• Grab a Mother Clucker at Hot Suppa | Address: 703 Congress St, Portland, ME 04012
• Take the Ferry to Peak’s Island | Address : 56 Commercial Street, Portland, Maine 04101
• Spend your morning experiencing the last of Portland: revisit Old Port, Portland Headlight, or explore the Portland Museum of Art
• Prepare snacks and drive 3 hours to Bar Harbor, where Acadia National Park is located
• Arrive and check into your accommodation in Bar Harbor
• Grab lunner at Galyn’s | Address : 17 Main St, Bar Harbor, ME
• Do some shopping and strolling in Bar Harbor – get some snacks for Acadia
• Get some rest!
• Start early – do a difficult hike on the Beehive Loop Trail or a moderate one on the Bubble Trail
• Eat snacks or your packed lunch at Sand Beach or Echo Beach
• Grab lunch or some popovers and tea at Jordan Pond House | Address : 2928 Park Loop Rd, Seal Harbor, ME 04675
• Drive to Cadillac Mountain and enjoy the views and Thunder Hole to check out the cliffs
• Finish your day in Bar Harbor at the Side Street Cafe | Address: 49 Rodick St, Bar Harbor, ME 04609
• Stop at the Bass Harbor lighthouse then make your 4-hour drive to Portsmouth, NH
• Grab lunch and ice cream – do some walking and shopping in Portsmouth
• Continue your New England road trip to Boston – check into your hotel
• Grab dinner – we got take-out pizza at a corner store and rested from our long drive
• Explore the Freedom Trail by walking to each site (3 miles long, but will take all day)
• Go whale watching at the Stellwagen Bank National Marine Sanctuary
• Explore the Boston Harbor: Charles River Esplanade, Museum of Science, Boston Children’s Museum, or Boston Tea Party Ships and Museum
• Check out the Italian Quarter in the North End
• Grab dessert at Mike’s Pastry | Address: 300 Hanover St, Boston, MA 02113
• Explore the college town of Harvard in Cambridge: Harvard Yard, Harvard Bookstore, Art Museums, Harvard Natural History Museum
• Experience New England candlepin bowling at Sacco’s Bowling Haven | Address: 45 Day St, Somerville, MA 02144
• Check out the iconic Fenway Park where the Red Sox play
• Walkthrough the New England Holocaust Memorial | Address: 98 Union St, Boston, MA 02129
• Grab lunch at the Boston Public Market | Address: 100 Hanover St, Boston, MA 02108
• Revisit Boston Proper – Edgar Allen Poe , and walking ghost tour , picnic in Boston Commons , do more shopping at Faneuil Hall Marketplace
• Grab dinner at the Cheers Restaurant | Address: 84 Beacon St., Boston, MA 02108
• Check out and return home

Map of the 10 Day New England Road Trip Itinerary

Options to Extend Your New England Road Trip Itinerary

If you have more time to spend on a New England road trip, here are a few other historic cities to stop: Concord, Massachusetts, New London, Connecticut, or Providence, Rhode Island.

• Concord, Massachusetts is also full of culture, museums, galleries, and shops. This was also the home to writers such as Emily Dickenson and Henry David Thoreau.
• Providence, Rhode Island is a small city with a lot of history and very friendly people. Be sure to check out the historic downtown area and the amazing restaurants.
• New London, Connecticut where you can visit the U.S Coast Guard Academy, Fort Trumbull State Park, and many more historical landmarks.

What to pack for your 10 Day New England Road Trip

Keep in mind that you’ll be in the car for a few hours, so also pack some comfortable clothes for a long New England road trip.

Boston can also be rainy, so you’ll want to make sure to have a rain jacket and/or water-resistant shoes for all the walking you’ll do.

Here is my recommended list:

• 4-5 tops or shirts
• 1 pair of leggings
• 1 pair of jeans
• 1 jacket (or rain jacket as it does get wet!)
• 1 pair of hiking boots or walking shoes
• 1 pair of sandals
• Sunscreen for Acadia

New England road trip itinerary

When is the best time to go on a 10 day new england road trip.

The best time for a road trip to New England is late spring through early fall. This region of the United States has a temperate climate with moderate temperatures, meaning you can usually avoid extreme heat or cold during these months.

In addition, this time of year offers more daylight hours and plenty of outdoor activities that are perfect for exploring!

You can also plan your road trip to New England during the autumn months, especially in late September to see the foliage change from green to beautiful oranges and reds. Take a drive through the White Mountains in New Hampshire for spectacular views of nature at its finest!

FAQs: 10 Day New England Road Trip Itinerary

Is boston worth visiting.

Absolutely! Boston is full of history and culture. From the Freedom Trail to Fenway Park, there are plenty of places to explore. The food in Boston is also fantastic with a variety of cuisines from Italian in the North End to seafood dishes on the waterfront.

How much money should I budget for a 10 day New England road trip?

It really depends on your budget and what activities you plan to do. For a mid-range budget, a good rule of thumb is to budget around $150-$200 USD per day for food and activities.

Accommodations tend to run between $100-$150 for stays that are close to the areas mentioned in this itinerary. Car rentals range between $80-$90 a day.

If you plan to travel with friends, you can save money by splitting the cost of the car rental and hotels. You can then set your own budget for food and fun activities.

Are there any special precautions I should take when driving in New England?

Yes, some roads can be narrow and winding so it’s important to be aware of the speed limit, road signs, and other drivers. It’s also a good idea to plan your route ahead of time so you know where you’re going.

You might find fog in the northern part of New England as well in the early morning. Be sure to know how to use your fog lights and take it slow.

When in Boston, be prepared for congested traffic, weird roundabouts, and confusing streets (from my own personal experience).

Final Thoughts: 10 Day New England Road Trip Itinerary

That’s a wrap on the ultimate 10 day New England road trip itinerary. New England is a beautiful destination with many historical landmarks, incredible coastal views, and delicious food!

Are you ready to explore New England? Check out these posts!

• 10 Day New England Road Trip (Portland to Boston)
• 3 Day Portland Itinerary
• Best Walking Tours in Portland
• One Day in Camden, Maine
• Boston to Wells Road Trip
• Day Trips from Boston by Train (MBTA Weekend Pass)

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My favorite travel tips + resources.

Here is a quick glance at all my go-to travel tips and resources that I use to plan every trip! For more information, check out my travel resources page .

• Booking flights: I use Google Flights to check all routes and find the best flights. Then I compare Skyscanner (for the lowest prices) before I book.
• For hotels, I go through Booking.com or book directly with Marriott (for points + rewards).
• When I travel internationally, I’ll book through Hostelworld for very budget-friendly stays.
• For vacation rentals, use Vrbo or Marriott Homes & Villas .
• Expedia also has some great bundles for hotels, flights, and car rentals altogether.
• Car Rentals: I love renting cars through Discover Cars . They have been consistent and provide the best customer service.
• Trains in Asia: Trip.com has the best options!
• Trains in Europe: Trainline or Omio .
• Visa Application: For a hassle-free process, apply for your visa from iVisa .
• Travel Credit Card: I book all my travel (flights, hotels, car rentals) through Chase Sapphire .
• Vaccines and Medications: Check the CDC website for updates on necessary vaccines to enter a country, including updates on Covid-19 and recommended places to visit. I recommend getting all the vaccines you need before you go!
• Tours + Experiences: I absolutely love my tours! Everything from eerie walking ghost tours to food tours, I’ll usually book something every trip either through Viator or GetYourGuide .
• Entertainment: Looking for entertainment like sporting events, theater shows, or concerts? Book with Ticket Squeeze !
• Tech : Keep your internet browsing safe, secure, and fast with ExpressVPN
• Language Learning: The best place to learn a new language is through Babbel as you travel to countries you don’t know the language.
• What to Pack: I almost always travel by backpack . For products I like, check out my packing guide page for all the things I take with me on different trips.

Pafoua is the author and creator of Her Wanderful World. Pafoua writes from her numerous excursions about all things travel, from fun itineraries to creating memorable experiences on the road. When she’s not traveling, Pafoua loves a fun board game night with her friends or is snuggled up reading a good book. You can find her on Instagram @herwanderfulworld.

10-Day New England Road Trip Itinerary

Whether you’re looking for a summertime family vacation, colorful fall foliage, or a romantic snowy winter getaway, the northeast corner of America makes for an ideal destination.

Being that most Americans only get two weeks of vacation time a year, we’ve planned this 10-day New England road trip strategically.

This itinerary includes the best places to visit in New England. You’ll get to experience everything from quaint villages to bustling cities and national parks, of course. Plus, there will be plenty of breathtaking scenery along the way!

So, grab your camera and get ready. It’s time to road trip New England and discover what this corner of America has to offer!

Where is New England?

New England is located in the northeastern part of the United States. It’s made up of six states: Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont. The region is known for its rocky coastline, autumn foliage, and cold, snowy winters.

New England trip planning tips

Even before you begin planning your New England road trip, there’s one absolutely essential thing you need to know: Hotels fill up very quickly.

To avoid disappointment, be sure to book all your accommodation as soon as you know your travel dates! We’re not kidding. People book months in advance to secure a place to stay.

Same with New England tours. They are extremely popular , especially in the fall and winter months. And it’s not just for road trips. Bostonians book these spots as weekend getaways as well.

If you plan to rent a car, do it ahead of time. Not only does that guarantee you the lowest rates, they’ll reserve the type of car you prefer.

Now that you have everything reserved, let’s set out on your road trip!

Day 1: Salem, Massachusetts and Portland, Maine

Most people plan their driving vacations from Boston because it has the largest airport in New England. Arrive at Boston Logan International Airport in the morning, pick up your car, and head out of town.

Your first stop will be Salem, where you’ll explore the city’s infamous witch history. Start at the Salem Witch Museum to learn all about the famous Salem witch trials of 1692. Then, visit the Salem Witch Trials Memorial near the water, and snap a selfie in front of the House of the Seven Gables, made famous by author Nathaniel Hawthorne.

For an in-depth look at the Witch Trials, book the Bewitched Walking Tour of Salem. A local historian will take you over a dozen locations in downtown Witch City and bring Salem’s history to life.

Finally, pop in at Red’s Sandwich Shop or Deli House for lunch. You can either dine in or order takeout and eat on the road, as you wish.

Now, continue your drive north to Portland, Maine’s largest city. Not counting stops, the journey takes about 90 minutes.

This lively city is full of great restaurants, bars, and shops, as well as plenty of art galleries and museums. If you’re interested in a guided tour from a local, the 2-hour Real Portland Tour has earned a Viator Badge of Excellence with over 1000 5-star reviews. (Book ASAP; it fills up quickly.)

Spend the rest of your afternoon strolling along the cobblestone streets of Portland’s Waterfront Old Port Historic District, touring the Portland Museum of Art, or visiting Victoria Mansion, a beautifully preserved 19th-century home.

End your day at the charming Old Port, where you can enjoy local history, foods & drinks.

Where to stay in Portland Maine

• Budget: The Black Elephant Hostel has air-conditioned accommodations, a shared kitchen, and a shared lounge, along with free WiFi throughout the property. Some rooms at the property feature a balcony with a garden view.
• Mid-range: Hampton Inn Portland Downtown Waterfront   offers free airport and local shuttles, an indoor heated pool, and a fitness center.
• Luxury: The Francis , a historic landmark, is located in Portland’s Bramhall neighborhood, near the Art District. Museums, galleries, theaters, skating rinks, craft breweries, and boutiques are within a 0.9 mi radius of the property.

Day 2: Acadia National Park Maine

It may look quite far on the map, but in reality, it only takes about three hours to drive from Portland to Acadia National Park. So get an early start and hit the road!

Acadia National Park is one of the most popular tourist destinations in Maine, and for good reason. Located on Mount Desert Island, Maine’s largest island, this 47,000-acre park is home to towering mountains, pristine lakes, and miles of hiking trails.

Here, rocks erode into the ocean and iconic lighthouses stand high above them. Wildlife can be seen both in the water and on land, and there are numerous hiking trails to explore.

Today’s first stop will be Bar Harbor, a beach town that’s also the gateway to Acadia National Park. You can take a walking tour through Bar Harbor before checking into your hotel, and then head to the park after lunch.

There are plenty of things to do in Acadia National Park, but some of the most popular activities include hiking to the top of Cadillac Mountain (the highest point on the U.S. Atlantic coast), kayaking in Swan Lake, and biking or driving the Park Loop Road.

To end your day, enjoy a dinner of ocean-fresh fish in one of the many excellent restaurants on the island .

ⓘ TIP: This inexpensive Acadia National Park Self-Guided Driving Tour is a personal guide, audio tour, and map all rolled into one. Simply download the app and connect to the car speakers; it’s yours to keep. Less than $15 for a guided driving tour of Bar Harbor and Acadia National Park? Yes please!

Where to stay near Acadia National Park (Bar Harbor)

• Budget: Various campgrounds are available in the area.
• Mid-range: Acadia Inn is a family-friendly hotel 1.1 miles from the center of town. The hotel offers a complimentary breakfast buffet each morning, free wi-fi, air conditioning, a hot tub and outdoor pool, and an on-site trail that accesses the park. 
• Luxury: Chiltern Inn Featuring an indoor pool and sauna, this Bar Harbor bed and breakfast is located 1.6 mi from Acadia National Park. Rooms at the Chiltern Inn offer a wood-burning fireplace, free Wi-Fi, and a private bath.

Day 3: White Mountain National Forest, New Hampshire

After spending two days in Maine, it’s time to head into New Hampshire. You’ll spend the morning on the drive from Acadia National Park to White Mountain National Forest, and the vistas are so beautiful you’ll thoroughly enjoy the long drive!

White Mountain National Forest tops most New Hampshire itineraries, with unnumerable towering mountains, pristine lakes, and miles of hiking trails to explore.

• Springtime brings warmer weather and melting snow, making it the perfect time to go hiking and camping.
• In the summer, you can go hiking, camping, fishing, and canoeing.
• In Autumn, you can explore the many covered bridges in the area and drive New Hampshire’s scenic Kancamagus Highway to see the famous New England fall foliage.
• And in winter, the mountains of New Hampshire turn into a playground for cold-weather sports enthusiasts, with numerous ski resorts and cross-country skiing trails.

No matter what time of year you visit, there are plenty of things to do in the National Forest. Some of the most popular activities are hiking to the top of Mount Washington (the highest point in the Northeastern U.S.), driving the scenic Kancamagus Scenic Byway, and photographing the many covered bridges in the area.

ⓘ TIP: Download this self-guided Kancamagus Scenic Byway driving tour to ensure you don’t miss anything on the way. Directions, local tips, and fascinating behind-the-scenes stories play automatically, based on your location. The app runs offline using GPS; no cell service needed.

Where to spend the night in the White Mountains

North Conway is the perfect end to your day in New Hampshire, as it has a wide range of lodging options. You won’t have any problem finding a place to eat either, as it has many of New Hampshire’s best restaurants, shops, and attractions.

• Budget: Colonial Motel features an outdoor swimming pool and a picnic area. Some rooms feature a covered porch while others have a large spa bath.
• Mid-range: Cranmore Inn bed and breakfast is a short walk from the Conway Scenic Railroad and Mount Washington Observatory Weather Discovery Center. It features uniquely-decorated rooms with free Wi-Fi.
• Luxury: White Mountain Hotel and Resort Set within the natural beauty of Hale’s Location, this elegant North Conway resort features a year-round heated outdoor pool and hot tub overlooking the mountains. Rooms feature flat screen TV’s, work desk, USB Ports and Speakman showers. Daily full breakfast is included and high-speed internet access along with two dining options with Ledges Restaurant and Tullamore Tavern are also provided.

Day 4: Vermont’s Green Mountains

Today is all about Vermont, the Green Mountain State. The state gets its name from two French words, vert (green) and mont (mountain). When you see these mountains, you’ll understand why!

This morning begins with a two-hour drive to Stowe Vermont. Stowe is a popular ski resort town in Vermont, with a charming downtown and a famous ski resort run by the Trapp Family, of Sound of Music fame.

Beyond Stowe itself, you can go for a hike in the Green Mountain National Forest, enjoy a scenic drive on the Mountain Road, or take a day trip that includes visiting a cider mill and the Ben & Jerry’s Factory (complete with ice cream samples!).

Vermont produces some of the best maple syrup in the world. Be sure to visit one of the many sugarhouses in the area to see how this delicious treat is made!

After lunch in Stowe, this afternoon’s road trip itinerary is all about the scenery as you drive down the Route 100 Scenic Byway. Vermont’s longest highway takes you through some of the most beautiful countryside in Vermont. You’ll see covered bridges, mountain vistas, and quaint towns all along the way.

Keep your camera handy; the covered bridges of Vermont are some of the most beautiful in New England. Visit Vermont has a page listing covered bridges along your drive.

Where to stay in Wilmington Vermont

Stop for the night in Wilmington, VT. Wilmington is a small town located in the southwest corner of the state, right on the border with Massachusetts.

This quaint town is home to several art galleries, antique shops, and a variety of restaurants. It’s also the perfect place to relax after a long day of driving.

• Budget: Viking Motel offers free WiFi access, cable TV, and air conditioning in all rooms.
• Mid-range: The Nutmeg provides accommodations with a garden and free WiFi throughout the property as well as free private parking for guests who drive. The inn features family rooms.
• Luxury: The Wilmington Inn provides accommodations with a bar, free private parking, a shared lounge and a garden. Featuring family rooms, this property also provides guests with a terrace. Free WiFi and a concierge service are provided. Vegetarian, vegan, and gluten-free options are available for breakfast.

Day 5: Litchfield and Mystic, Connecticut

Your first stop today is the small town of Litchfield, located in the western part of Connecticut. The prettiest drive is down US-7 S, and it travels through Litchfield Hills, one of the nicest parts of Connecticut. This route takes roughly the same amount of time as I-91 (about 2.5 hours). You decide!

Litchfield is a charming New England town with a rich history. The town was founded in 1719 and has been home to many notable residents over the years, including writer Harriet Beecher Stowe and abolitionist John Brown.

Today, Litchfield is a popular tourist destination for its many antique shops, art galleries, and historic homes. If you’re interested in learning more about the history of Litchfield, be sure to visit the Litchfield History Museum.

You can also take a self-guided walking tour of the town’s historic homes and buildings, such as the Oliver Wolcott House.

After lunch in Litchfield, your New England road trip continues east to Mystic, Connecticut. Mystic is a historic seaport located on the Mystic River in southeastern Connecticut.

Today, Mystic is a popular tourist destination, best known for its maritime history and as the setting of the 1988 film Mystic Pizza.

The top attraction is Mystic Seaport Museum, which is one of the largest maritime museums in the world. This fascinating museum features exhibits on the history of whaling, shipbuilding, and seafaring.

If you’re looking for other things to do in Mystic besides visiting the museum, one of the most popular family attractions is the Denison Homestead , a 300-year-old family farm that offers a glimpse into early colonial farm life. Mystic also has a nice aquarium, which is a popular attraction on rainy days.

Outdoor options include hiking in nearby Bluff Point State Park and kayaking or canoeing on the Mystic River. You can also take a boat ride or go for a walk along the pretty waterfront.

Where to stay in Mystic, CT

• Budget: Pet-friendly Days Inn Mystic is within walking distance to sights in downtown Mystic, and a short drive away from the Atlantic Ocean. Free breakfasts, Wi-Fi, and onsite parking is included.
• Mid-range: The Taber Inne is an 8-minute walk from the beach and 2,300 feet from Williams Beach Park. Guests staying at the hotel can enjoy the indoor heated pool and free WiFi throughout the property.
• Luxury: Harbor View Landing  accommodations include cottages, free WiFi throughout the property, and free private parking for guests who drive. Featuring water sports facilities and a tennis court, the hotel is close to several noted attractions and only 1.8 miles from Mystic Seaport. The property has river views and a terrace.

Day 6: Newport, Rhode Island

Rhode Island, the smallest state in the U.S., is home to many historic towns. One of the most notable is Newport, which was once a summer retreat for the wealthy.

The seaside town of Newport is best known for its gorgeous mansions, which were built by some of America’s wealthiest families during the Gilded Age.

Start your visit with a tour of The Breakers, the grandest of all the Newport mansions, located on the elaborate estate of Cornelius Vanderbilt. Then, explore the grounds of Marble House, another one of Newport’s famous Gilded Age mansions. Be sure to also stroll along Bellevue Avenue to see all of the other lavish mansions that line this famous street.

ⓘ BUDGET TIP: If you take the Newport Scenic Trolley tour , free admission to The Breakers mansion is included.

In the afternoon, visit the International Tennis Hall of Fame, explore Fort Adams State Park, or relax on one of Newport’s many beaches. If you’d prefer to explore Newport itself, cobblestone streets, art galleries, museums, antique shops, and local restaurants await.

If you’re a water lover, consider taking a boat ride to Block Island, taking a scenic boat ride around Newport Harbor, or going for a sail on Narragansett Bay.

End your day with dinner at one of Newport’s great restaurants, and don’t forget to enjoy a delicious cup of coffee from one of the local cafes while you’re there!

Where to stay in Newport Rhode Island

• Budget: Near Newport’s Memorial Park, Motel 6 Newport offers free basic WiFi and rooms that feature a seating area. The Newport Marina is 2 miles away.
• Mid-range: The Admiral Fitzroy Inn , a historic bed and breakfast, offers elegantly decorated guestrooms featuring antique sleigh beds and hand-painted walls. Guests staying at the inn can enjoy a free gourmet continental breakfast served in the sunny dining room overlooking Thames Street. The property also features a rooftop deck.
• Luxury: Hotel Viking opened in 1926. This historic Newport hotel is a 5-minute walk to Thames Street and less than 1 mile from the Cliff Walk to the city’s historic mansions. Guests staying at the Viking Hotel can enjoy an on-site spa, indoor pool, and fitness center. On-site dining at the One Bellevue restaurant is also available.

Day 7: Cape Cod

You’ll spend today on Cape Cod, a peninsula located in southeastern Massachusetts. With nearly 560 miles of pristine coastline, Cape Cod has long been a popular summer destination for the rich and famous, including the Kennedy family, who have a compound in nearby Hyannis Port.

But it’s a favorite East Coast vacation spot for families, couples, and singles as well, because of its many beaches and quaint small towns. New England beach vacations are extremely popular.

Depending on the weather and your energy level, you might want to begin with a Cape Cod self-guided driving tour. The audio app gives you a flexible and affordable way to see all of the scenic Cape Cod on your own terms.

Alternatively, start your morning at Cape Cod National Seashore. With 40 miles of coastline, the seashore features many pristine beaches, hiking and biking trails, and lighthouses to enjoy.

After a few hours at the seashore, drive to the charming town of Sandwich for lunch. This historic town is home to many beautiful old homes and buildings, including a glass museum and Hoxie House, the oldest home on Cape Cod. Heritage Museums and Gardens is also a wonderful destination.

In the afternoon, head to Provincetown, located at the very tip of Cape Cod. Provincetown is a popular summer destination for its nightlife and vibrant arts scene. It’s also a great place to enjoy some fresh seafood.

Or, you could take a boat ride to Martha’s Vineyard or Nantucket. These two islands are both accessible by ferry from Cape Cod and offer a different vibe than the mainland. If that’s more your speed, consider this Martha’s Vineyard tour by a local who has lived his whole life on the island.

Other popular Cape Cod attractions include the Cape Cod Museum of Natural History (Brewster, MA), the Whydah Pirate Museum (West Yarmouth), and the scenic Cape Cod Trail, a 22-mile paved pathway that winds through 6 towns on the Cape.

Where to stay in Cape Cod

You can either stay in Cape Cod for the night or return to the mainland in the evening and stay in Plymouth for two nights.

• Budget: Viking Shores Motor Lodge , located 2 mi from the beach, features an outdoor pool. It is also a part of the Cape Cod Rail Trail Bike Path.
• Mid-range: Sandbars Inn in North Truro has air-conditioned accommodations with views of the sea and free WiFi. Some of the units have cable TV, a fully equipped kitchen with a dishwasher, and a private bathroom with a shower and a hairdryer.
• Luxury: Wequassett Resort and Golf Club is a 2-minute walk from the beach. This West Harwich waterfront resort offers an 18-hole golf course, free Wi-Fi, and brightly colored rooms that offer a sitting area and plush bedding. Guests can enjoy waterfront dining, swim in the seasonal outdoor pool, or relax in the hot tub. A fitness center, children’s playground, and tennis court are also available.

Day 8: Plymouth, Massachusetts

The town of Plymouth, Massachusetts began as a Puritan colony in 1620. Today, it’s best known as the site of the first Thanksgiving and home to Plymouth Rock, the famous landmark that marks the spot where the Pilgrims first landed.

Start your visit at Plimoth Patuxet (formerly known as Plymouth Plantation). This living history museum complex is a must-visit for families and history buffs. It includes a replica of the Mayflower ship and several original 17th-century buildings that you can visit.

After lunch, stop at Plymouth Rock for a photo and continue to Pilgrim Hall Museum in Plymouth’s historic downtown-harbor area, where you can learn all about the Pilgrims who settled in Plymouth in 1620.

The town’s downtown-harbor area contains several historic buildings, including the Plymouth Courthouse (built in 1754), the Jenney Grist Mill (built in 1636), and the Mayflower Society House (built in 1824).

End your day with a walk along Plymouth’s historic waterfront. Don’t miss the Plymouth Cordage Company Historic District, a National Historic Landmark that includes several 19th-century rope-making factories.

End your day with dinner and a stroll along the Plymouth Waterfront to watch the sunset over Cape Cod Bay.

Where to stay in Plymouth:

• Budget: Best Western Plus Cold Spring  features an outdoor pool with panoramic views of Cape Cod and rooms with a 32-inch LCD TV. Historic Plymouth Rock is less than one mile from this hotel. Plymouth Waterfront and the Mayflower II are both within a 20-minute walk from this hotel. The Plimoth Plantation is just a 5-minute drive from the hotel.
• Mid-range: Hotel 1620 Plymouth Harbor  is located across the street from historic Plymouth Harbor. It features an indoor heated swimming pool.
• Luxury: Rooms at Harbourtown Suites on Plymouth Harbor include a seating area with a sofa bed, a kitchen with microwave and dishwasher, cable TV, free Wi-Fi, and free private parking.
• Resort: Mirbeau Inn & Spa has a spa and wellness center, a restaurant, and a fitness center with Peloton® bikes. The accommodation includes a fireplace and free Wi-Fi access. Other facilities offered at the property include an onsite shop and free parking.

Days 9-10: Boston, Massachusetts

There’s no better place to cap off your 10-day New England road trip itinerary than in Boston, the capital of Massachusetts. This historic city is full of colonial character and charm. Plus, there are plenty of things to see and do, from exploring the Freedom Trail to watching a baseball game at Fenway Park.

Return your rental car before you do anything else. You won’t need it in the city, as you can navigate better by using Boston’s public transportation system and on foot. Besides, parking and traffic in Boston can be a hassle.

You’ll find details on how to get into Boston from the airport at the end of this article.

ⓘ PRO TIP: If it’s too early to check into your room when you arrive, don’t worry. Most hotels will stash your bags in a secure location and then deliver them once your room is ready.

As one of America’s oldest cities, Boston Massachusetts is full of historic landmarks and sites. Start your Boston adventure by walking the Freedom Trail. Known as one of the top things to do in Boston, this 2.5-mile (4 km) trail passes 16 different sites that are all significant to American history. You can do it yourself or get the full experience with a guided walking tour.

If time permits this morning, take a leisurely stroll through Boston Common, the oldest public park in the country.

Head to the iconic Quincy Market shopping district for lunch, and don’t forget to try a famous Boston Cream Pie while you’re there!

In the afternoon, choose activities based on your interests:

• History lovers – visit some of Boston’s famous historical sites, such as the Boston Tea Party Ships, the USS Constitution Museum, and the Paul Revere House.
• Sports fans – Tour Fenway Park, home of the Boston Red Sox baseball team
• Art lovers – stroll through the Isabella Stewart Gardner Museum or the Museum of Fine Arts

In the evening, dine at one of Boston’s many great restaurants. For a truly unique experience, try a seafood dinner at one of the city’s many waterfront seafood shacks.

Be sure to end your day with a stroll along the waterfront to watch the sunset over Boston Harbor.

Where to stay in Boston:

• Budget: in the heart of Boston, HI Boston is 5 minutes away from Boston Common and public transport. All rooms include free Wi-Fi. Guests can relax with a pool table and TV in the game room. A shared kitchen, coffee bar, and vending machines offering snacks and drinks are on-site. Bike storage is available.
• Mid-range: The Oasis Guest House offers free WiFi, shared outdoor terraces, and concierge service. Northeastern University is an 8-minute walk. Some rooms include a private bathroom. All rooms are nonsmoking.
• Luxury: The Newbury Boston  features a restaurant, bar, shared lounge, and garden. This 5-star hotel has a 24-hour front desk, room service, and free WiFi. The hotel has family rooms, and breakfast includes vegetarian and gluten-free options.

Day 10 of your New England itinerary depends on when you plan to depart.

If you’re leaving in the afternoon or evening, you have time this morning for a little more sightseeing. You could spend a couple of hours cruising on Boston harbor or go wandering through one of Boston’s neighborhoods before heading to the airport.

If you have a second, full day in Boston—or better yet, 3 days in Boston, you might want to take part in an interactive museum tour and become a part of the Boston Tea Party , take an Italian food tour in Boston’s North End, or go whale watching off the coast of Boston in a catamaran. If you plan it right, you might even be able to catch a Red Sox game at Fenway Park!

No matter when your flight departs, be sure to allow plenty of time to get to Logan Airport. Traffic can be heavy, especially during rush hour.

How to get to downtown Boston from Logan International Airport

The cheapest and easiest way to get to downtown Boston from Logan International Airport is by taking the MBTA (Massachusetts Bay Transportation Authority) Silver Line bus. The SL1 and SL2 buses both go to South Station, which is located in the heart of downtown Boston. The ride takes about 30 minutes and costs $2.75 per person.

However, it’s not that easy because you’ll still need to get to your hotel. It’s best to take a cab or Uber from the station to avoid hassling with luggage on public transportation.

The most convenient option is to book a private shuttle from the airport to your hotel and let someone else handle the bags and traffic.

Final thoughts about this New England road trip itinerary

And that’s a wrap on your 10-day New England road trip itinerary! We hope you enjoyed this trip and that you’ll come back to explore more of this beautiful region in the future.

What are the best months for fall colors in New England?

The best time to visit for fall foliage in New England is typically September and October. However, the exact timing for peak color can vary from year to year depending on weather conditions.

Use this map to find up-to-date information on current New England fall foliage color.

5 tips for taking a road trip through New England

1. Get a map. You’ll be traveling through some remote areas with spotty or no cell signal. If you don’t want to risk taking a wrong turn, either buy a paper New England map or download the offline version of whatever New England road trip map application you use. And if you can, familiarize yourself with it before you depart.

2. Use apps to find cheap gas. Two popular ones are Gas Buddy and Waze . Fuel always ends up being one of the most surprising and costly expenses on a road trip.

3. Track the weather daily. New England weather can be finicky, and changing conditions can take you by surprise. Keep a raincoat and sweater handy.

4. Book a few experiences along the way. Walking tours, food tours, and boat tours are a lot of fun and create wonderful memories. There are tons of great tours on offer, allowing you to get the most of the vast history and beauty that New England has to offer.

5. Always carry loads of water and snacks in the car. It’s convenient to have what you need on hand. Plus, you won’t waste time and money buying stuff at a convenience store.

5 New England photography tips

1. Rural country roads offer a wealth of photo opportunities, from quaint farms to rolling hills. These areas are often more rural and less populated than urban areas, so you’ll have plenty of chances to snap some beautiful shots. And because rural country roads are usually less crowded than city streets, you won’t have to worry about getting in anyone’s way.

2. Look for elevated vantage points whenever possible. While you’re out exploring, keep your eyes peeled for elevated vantage points. hop on a rock or climb a tree to get a better view of your surroundings. You might just be surprised at what you find!

3. Remember to keep your camera charged. That way, you’ll never miss a moment. A fully charged hattery will let you capture all the special moments, so always keep it topped up.

4. Bring multiple spare batteries for your camera. Nothing is worse than seeing a great shot and discovering your camera is out of power. Extra batteries are the best backup plan.

5. Bring your drone, if you have one. You’ll be glad to know that aerial photography is permitted in many parts of New England.

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Written by Linda

Linda is multilingual and has been to over 50 countries. Her insatiable love of travel, cuisine, and foreign languages inspired her to create As We Saw It, where she documents her trips, shares practical itineraries, and offers insider tips. She’s passionate about helping fellow travelers save time, money, and hassle, and loves to discover new places to explore.

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New England Summer Road Trip (One Week Itinerary)

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My mother grew up in a small lake town in Western Connecticut. I suppose that’s how it all started, the annual family New England road trip. 

I was born and raised in NJ, but really, m y brothers and I grew up New England. Our summer and holiday weekends were often spent on that grueling strip of I-95 that stretches between New Jersey and the northern part of the country.

Between my grandparent’s house in Connecticut, a beach house in a small fishing village on the coast of Rhode Island, and my father’s annual meeting in Bar Harbor, Maine, I got to know New England intimately. It has some of my happiest childhood (and later, adulthood) memories.

Long after my family had drifted apart and those road trips stopped I continued to explore, taking my own family (AKA Joe and Della pup) along this very route.

New England is downright gorgeous.

It’s allll the cliches. Small cities filled with charming cobblestone streets, tiny, snow covered homes, and old-school Main Streets. 

It’s also small geographically. Like, you can drive from the tip of Connecticut to the tip of Maine in half a day, small. 

Though we won’t be doing that here. Here, we’re showing you how to take your time and absorb some of the most scenic spots — filled with the best food, obviously — in a week’s time.

In this one week New England road trip itinerary we’re sticking to the New England coast, perfect for cruising in the Summer or Fall months.

P.S. Going for longer than a week? Check the end of the post for suggestions on how to extend your road trip through other New England hot spots.

Table of Contents

Steps to Plan the Best Road Trip in New England

1. Plot your route

Where are you leaving from? What are your “can’t misses?” Where do you want to stay? Our itinerary below is a guide…you can follow it exactly (because it’s freaking awesome) or you can pick and choose which works best for you to form your own path.

2. Check your route against the weather. 

This is so often overlooked! Plan your route as loosely as possible. This way, you can quickly pivot if the weather is threatening to ruin your plans. It allows you more flexibility, so when there is rain forecast on the day you want to go to Acadia National Park, you can easily switch it to another.

Obviously take this with a grain of salt…weather is weather, and in New England, weather is usually unpredictable, so bring a sense of humor. As they say up around here:

“There’s no such thing as bad weather, just bad clothing” or, my personal favorite, “If you don’t like the weather, wait 15 minutes” 

3. Follow your heart

This applies to every travel experience. If you plan an activity and it sucks, BAIL. If you find a local seafood restaurant on the side of the road where a grandma-looking lady is frying fish …slam on those breaks immediately. 

When should you go on a new england road trip?

I’m going to say that SUPER annoying thing we all hate and say…it depends! Road trips in New England can vary depending on the weather. Let’s break it down by season:

How does this itinerary work?

This itinerary leaves from the New York City metro area, but you can hop on or off at any point along the way. 

If you’re in upstate New York simply head west until you reach I-95 (or check out these New York day trips instead.

Leaving from further South? Trying extending the road trip through Philadelphia– stopping for a pizza break –or go for a scenic run on the New Jersey shore .

One Week New England Road Trip Itinerary

Day 1 Connecticut

Start your New England road trip off by cruising north from New York City and into Connecticut, possibly the most underrated of the New England states. The southern part of the state is mostly made up of wealthy New York City suburbs, so we’ll skip right over that. 

The first stop will be a welcome break from the traffic you’ll likely be sitting in on I-95. New Haven is known for two things:

1. Yale and–more importantly in our book– 2. P izza

We’re the type of people who took a train to Naples just to eat pizza for 6 hours straight, so you know we couldn’t miss the opportunity to explore what folks claim to be the best Napoli style pizza this side of the Atlantic.

The best pizza in New Haven is debated with a ferocity that you probably don’t need to involve yourself in as a brief visitor.

Instead, just trust us and head to Modern Apizza for the best pie in the city. 

Or, if you want to do the tourist thing, check out the clam pies at Frank Pepe Pizzeria Napoletana. It wasn’t our favorite, but its been around for almost 100 years (which earns lots of respect in its own right).

Expect to wait in line for hours if you choose this spot.

If you’re one of THOSE people who don’t like pizza, there’s a great selection of taco trucks in a parking lot next to I-95. This is the spot to sample actual Mexican food, like beef tongue and tripe. 

And if you don’t like pizza or tacos…you’re honestly on the wrong blog.

Once you’re done consuming your body weight in pizza and/or tacos, hop back in the car and drive an hour north to Mystic, Connecticut. 

This little seaside town is a straight charmer. Fun fact: it’s also where the ultra-80’s classic Mystic Pizza was filmed, much to my mother’s delight. It’s worth spending a night here to tuck into one of the many B & B’s and snuggle up next to your boo.

Mystic Aquarium is great for all you fellow marine nerds (good for the kiddos and rainy days, too). When you wake up in the morning, head to Kitchen Little at Mystic River Marina, order the Lobster Benedict, and then call me immediately to thank me for starting your day off with such a marvelous treat on your tongue.

Where to Eat in New England

• Pizza at Modern Apizza , 874 State St, (203) 776-5306 http://modernapizza.com/
• Tacos at T aco trucks , 351 Long Wharf Dr in Long Wharf Park, varied
• Lobsters Benedict at Kitchen Little , 36 Quarry Rd, (860) 536-2122 https://kitchenlittle.org/

Where to Stay in Mystic, Connecticut

We’ve actually never stayed in Mystic ourselves so can’t personally recommend anything, but taking a dip in the gorgeous looking pool at House of 1833 Bed and Breakfast feels like something we’d be very into.

Days 2-3 Narragansett, Rhode Island

The smallest state in the union is also one of our favorites. Rhode Island is not, in fact, an island as I’m sure you’re all aware. However, thanks to its 400 miles of coastline, it still lives up to its “Ocean State” nickname. 

Rhode Island beaches are the main thing that draws us here every summer, though you could easily spend time praising the marshy and wooded trail walks as well.

Up north near Newport, beaches are steep rocky cliffs lined with old mansions. Down in the southern edge of the state–our fave–beaches are soft, sandy strips backed by grassy dunes.

Specifically, it’s the beaches in Rhode Island’s South County that have captured our hearts. They’re the reason we go back year after year, aside from the fact that we have family there.

Plus, this area is filled with some of our favorite seafood restaurants of all time.

These are some of our favorite South County beaches:

• Galilee Beach – little bit more of a local scene on a GORGEOUS beach
• Narragansett town beach – go surfing (or hang and watch!)
• Point Judith Lighthouse – rocky cliff facing out to the sea, can catch sunset views here depending on the time of year

Narragansett is a great little town to use as your home base here. It’s the home of URI and has a smattering of chill beach bars and delicious food.

Between beach trips, h ead into town for a fresh juice or smoothie at the hole-in-the-wall Crazy Burger , or do a fancy pants date night over at Coast Guard House , where you can sip on chowder while watching the Atlantic Ocean crash into the rocks outside the oversized glass windows.

If you really want to enjoy the scenery and the locavore seafood here, though, hop in the car and ride over to Matunuck Oyster Bar . 

Perched on the marsh where the oysters are grown, owner and aquaculturist Perry Rasso has grown this restaurant into a gorgeous indoor-outdoor space, serving up oysters as soon as they’re pulled from the water.

Our trips to Matunuck Oyster Bar usually consist of us waiting two hours for a table outside, cracking open a bottle of champagne, and watching the tide roll in and out while we slurp down dozens of our favorite salty little bivalves.

Honestly, I could (and usually do) spend a week here in Rhode Island and go nowhere else. It is the ultimate combination of rest, sweet salt air, and ultra-fresh seafood that my body craves after a long winter.

But you’re on a mission to explore New England on this road trip, so stop off for a night or two and then head North.

Where to Eat in Narragansett, Rhode Island

• Oysters at Matunuck Oyster Bar , 629 Succotash Rd, Wakefield, RI (401) 783-4202 https://www.rhodyoysters.com/
• Chowder and clam cakes at Iggy’s Doughboys , 1151 Point Judith Rd, Narragansett, RI (401) 783-5608 https://www.iggysri.com/chowda
• Coast Guard House , 40 Ocean Rd, Narragansett, RI (401) 789-0700 https://thecoastguardhouse.com/
• Crazy Burger , 144 Boon St, Narragansett, RI (401) 783-1810 http://www.crazyburger.com/

Where to Stay in Narragansett, Rhode Island

We’ve stayed at the Aqua Blue Hotel before which was ok (the location is AMAZING literally steps from the beach and Coast Guard House for dinner, although you pay for that) but we’ve heard GREAT things about The Break Hotel .

Days 3-4 Massachusetts

Hop back on I-95 and head north until you hit Boston, your next stop on this New England road trip.

Boston is a little city that feels like a little city, but with a bunch of strangely aggressive folks who drink a lot. I don’t mean that as an insult…Boston is a lot of fun. And being from New Jersey where people also tend to be angry at random times, these are my kind of people.

In all seriousness, Boston epitomizes so much of what is great about New England in an urban setting. The cobblestone streets are crammed with history and lined with tiny row houses that look straight out of a Charles Dickens novel. 

Fenway Park , the oldest operating baseball stadium in the country, sits in a charming downtown neighborhood with great food.

Boston’s Little Italy in the North End still has pasta cooking grannies rolling out dough by hand, and there are a delightful craft beer and food options everywhere you look.

The harbor is kept shockingly clean (coming from New York) and love it or hate it, Cambridge and Harvard are downright stunning.

Spend a full day exploring the historical sites, catching a Red Sox game, or touring the eclectic Harpoon brewery on the harbor. 

I’m also a sucker for the original Legal Sea Foods, though it’s recently moved and I’m not sure it’s worth it without the nostalgia factor.

Before you continue on your New England road trip, make time for a quick pit stop in Ipswich, MA.

It’s an adorable little town jutting out into the Atlantic Ocean that also happens to have some of the best fried clams EVER! Argue it…I dare you.

Then, continue North… 

Where to Eat in Massachusetts:

• Clam Box , 246 High St, Ipswich, MA (978) 356-9707 http://www.clamboxipswich.com/
• Legal Sea Foods , 55 Boylston St., Chestnut Hill, (617) 277-7300 https://www.legalseafoods.com/
• Giacomo’s , 355 Hanover St (617) 523-9026

Where to Stay in Boston, Massachusetts:

There’s literally an option for anyone when it comes to hotels in Boston. Click here to see a full hotel list with 100’s of options in every budget and style.

Day 4-6 Maine

Maine, you crafty, beautiful genius! How did you get to be so wild and stunning?

The lobsters…the pine trees…the rocky majestic coast…Maine is the epitome of when you just can’t even.

Here’s how you spend 2 days in Maine.

First off, go to Acadia National Park . Just go right there. Because as beautiful and amazing as much of the rest of the state is…Acadia is the masterpiece of it all.

Plus, with only a couple of days to explore, it’s the easiest way to see the best of what Maine has to offer.

Camp inside the park (Blackwoods Campground is the best if you can get in) or head downtown to Bar Harbor for a home base. Hotels here aren’t cheap, though, so plan ahead for this.

Take whale watching trips off the coast, hike the winding ocean-view hugging trials, scramble up rock faces, or just eat lobster rolls every hour on the hour.

One time, Joe ate lobster for every single meal for a week straight in Bar Harbor…it wasn’t cheap or particularly healthy, but it was impressive. And, he was happy. 

You can see the first sunrise hitting the continental US from Cadillac mountain (note: this gets really crowded) and head down for early morning blueberry pancakes at Jordan’s Restaurant.

Or, head out to pick wild blueberries yourself. They’re much smaller than the traditional grocery store ones, all the easier to pop them in your mouth like candy.  In season, you can find them hugging the trails, or you can stop by a local farm.

Where to Eat in Maine:

• Fresh boiled lobsters at Thurston’s Lobster Pound , 9 Thurston Rd, Bernard, ME (207) 244-7600 https://www.thurstonforlobster.com/
• Lobster rolls at Thirsty Whale , 40 Cottage St, Bar Harbor, ME (207) 288-9335 https://www.thirstywhaletavern.com/
• Blueberry pancakes at Jordan’s Restaurant , 80 Cottage St, Bar Harbor, ME (207) 288-3586 http://www.jordansbarharbor.com

Where to Stay in Bar Harbor, Maine:

Bar Harbor Inn is where I stayed every time growing up. Even after decades in use, it’s managed to stay modern and refined. I love the charming rooms, elegant feel, and actually good breakfasts here. Oh, and it just so happens to be on the ocean (think listening to the waves crashing on the rocks beneath you…DREAMY). Granted…my parents were floating the bill then, it’s not cheap, but SO worth it if you can swing it.

Click here to book The Bar Harbor Inn if you want to ball out on some luxury.

Or try Camping at Acadia National Park .

Day 7 On the road back home.. .

Head home, OR just never leave, We won’t judge.

Not sure where to stay? Use the search box below to find the best hotels in Connecticut, Rhode Island, and everywhere else in gorgeous New England.

Options to extend your New England road trip:

Add a night, day, or as long as you’d like on through some of these great additions:

• Portsmouth, NH – this trendy little harbor town gets its fair share of local tourists but isn’t often on the radar for outsiders. Be in the know and visit.
• Portland, Maine – one of our all-time favorite cities, Portland feels more like a small town, albeit one on the rugged Maine coast that happens to have exceptional dining.
• Burlington, Vermont – a hippy college town at it’s finest, lake-front Burlington is a bit out there but well worth the segway.
• Cape Cod, MA – come for pictures of the wood-shingled beachfront mansions, stay for the local pubs serving up piping hot seafood chowder and freshly fried, fish.
• Block Island , RI – this reminds us a lot of Ireland, it shares the romantic feelings and rolling, green hills. We like to take the ferry over and rent a bike, which will easily take you around the entire island.
• Kennebunk, Maine – Which we hit up on a different new England road trip (also where that lobster roll pic was born!!)

Road Trip Destinations in New England

It’s worth time to come up to New England just to stop at any one of these spots.

• Acadia National Park – For the unreal, oceanfront hiking.
• South County Beaches – For pristine, sandy beaches.
• New Haven – For the pizza and tacos.
• Boston seaport – For the charming, small city feel.

What is there to do in New England in Summer?

Soooo many things! 

• Bake your skin on the sandy beaches
• Hiking! Best in the Northern parts in my opinion (Vermont, New Hampshire, and Maine) but there are still great forested trails in Connecticut and marshland walks in Rhode Island
• Kayaking, canoeing, and stand up paddleboarding on lakes, rivers, marshes, and the Atlantic Ocean…oh my!
• Eating all of the fresh, local seafood like a maniac

New England Road Trip Map

We are the dynamic running duo that run this site. Lovers of new places, bridges, and all the food.

Returning to NYC / New England for first time in 20 years for family road trip. . Grew up on Pepe’s and Modern Pizza, and many other things you mentioned about Connecticut were spot on, love the recommendations throughout your articles. Will be using a lot of this information to help plan out our New England Summer vacation. Thank you for taking the time to share.

Thanks Frank! So glad you found it helpful

Should we travel on over to Plymouth since we’d be so close?

Hey Charlene, that’s a great idea! We’ve actually never visited Plymouth but from what I’ve heard about it I’m sure it would make a great addition

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The Perfect 7 Day New England Fall Road Trip Itinerary (+Scenic Drives!)🍁2024

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A New England fall road trip is the best way to experience the magical season of fall. The fall foliage in the region is some of the best on earth, and everyone should see fall in New England at least once in their life. In my opinion, a New England fall road trip is a true bucket list item .

Besides the picture-perfect autumn leaves in every direction, the orchards, fairs, and fall events create a cozy and memorable atmosphere you just won’t find elsewhere.

I’ve spent dozens of fall seasons in New England, both living and visiting, and if you’re looking for the ultimate New England fall road trip itinerary, I can help! I’d love to share with you my favorite spots where you’ll see incredible views, find the most colorful of leaves, and feel entirely like you’ve stepped into an autumn storybook.

PS: Don’t feel like planning your own road trip through New England? Consider joining one of these guided New England fall foliage tours which will do all the heavy lifting for you.

Table of Contents

Where Should You Go on a New England Fall Road Trip?

I want to start by saying that this itinerary is not comprehensive for all six New England states. 

If you want to see ALL of New England, you’ll need more time than what I’ve included here.

For a comprehensive regional journey, I suggest checking out my complete New England Road Trip Itinerary . This flexible road trip is designed for any time of year, not just to highlight the fall foliage, and includes every single state in New England.

In this post, I’ve included options for a 10, 7, and 5 day New England fall road trip. The itineraries I’ve put together focus largely on Vermont and New Hampshire . Both Vermont and New Hampshire are famous for their outstanding fall colors, which is why the trip focuses on this area.

But the southern New England states experience their share of gorgeous fall color as well. If time allows, I absolutely recommend venturing further into New England. Autumn’s glory is found in every single corner of this region.

New England Fall Foliage Road Trip: Essential Info

Let’s talk planning your fall road trip in New England.

You may be wondering: what is the best month for a New England fall road trip? When is the best time to visit New England for fall colors? When do the fall colors in New England peak?

Quick note about fall foliage in New England:

Foliage conditions vary each year due to that year’s temperature, rainfall, and other factors.  Some years have an earlier or later peak, or a more dramatic show of colors. Some foliage seasons are short, and some last a bit longer.

However, even with some variation, you can typically expect to see fall foliage in New England from early/mid-September through the end of October.

Peak foliage, when the leaves are at their best and brightest of the season, typically hits in early to mid October .

The foliage develops from north to south, with northern spots like Vermont, Maine, and New Hampshire generally experiencing “peak” before Massachusetts, Rhode Island, and Connecticut.

Yankee Magazine’s Peak Foliage Map is a perfect visual representation of the fall foliage progression in the region, and you can follow this real time fall foliage tracker for the northeast here and plan your best driving route for fall foliage colors that way, too!

Planning Your Trip

Now that you know approximately when to road trip through New England, you’ll have to decide how long your trip will be.

In my experience, 7 days is the perfect amount of time to explore. It gives you enough time to stop and visit a few destinations, while also allowing for flexibility as you go.

After all, driving is a big part of any road trip. You want to have plenty of time to take it slow, head off the beaten path, or even change your route.

It’s a good idea to stay flexible on a trip like this, as you can’t predict where the absolute best places for foliage will be, and sometimes, just heading a few miles over can make all the difference!

I’ve also created a 5 day itinerary as well as a 10 day itinerary, so you can easily customize your adventure to your needs.

Want to make your trip even longer? Go for it! You can use this northeast fall road trip itinerary as a starting point and expand as desired!

And if you only have a day or two, consider taking one of these scenic fall foliage drives . These shorter fall road trips around New England can be found in every single state.

🚗 Renting a Car: If you’re flying into New England, you’ll need to rent a car for this autumn road trip! I suggest checking out the best rates at Discover Cars.

Tips for Your New England Fall Road Trip

To have the best experience possible, here are some things to keep in mind:

• Make reservations for accommodations and popular attractions well in advance, as this is one of New England’s busiest times of the year.
• The best advice for what to pack for fall in New England is to bring layers. Temperatures can fluctuate throughout the day, and you’ll likely work up a sweat during any hikes or walks.
• It goes without saying that you should always drive carefully, but be aware that this busy tourist season often creates crowds and may even cause slowdowns on roads along popular “leaf-peeping” routes.
• Bring a quality camera to capture the stunning autumn landscapes, and maybe even binoculars for spotting wildlife. If you primarily use your phone for photos, like I do, don’t forget a car charger!
• Don’t leave New England without indulging in its fall culinary delights, including apple cider donuts, pumpkin pie, and hearty clam chowder.
• Consider downloading your road trip routes onto your phone with Google Maps to be used offline, as cell service can be spotty, especially in the mountains.
• Admire the scenery while being mindful of the environment; practice leave no trace principles and respect wildlife habitats.
• Pack a first aid kit, flashlight, extra water, blanket, and snacks in case of unforeseen circumstances. It’s always smart to be extra prepared for a road trip.

7 Day New England Fall Road Trip Itinerary

Now let’s dive into the details: where will this New England fall foliage road trip take you?

The main itinerary I’m going to share in this post is this: a one week New England fall road trip. Later, you can read my variations, which offer options for both shorter and longer road trips. We’re going to start this road trip in Boston, which, with its massive Logan International Airport, is the most logical starting point for someone visiting New England from elsewhere.

But don’t skip Boston, if you have time! It’s a classic, deeply historic New England destination that is absolutely worth a visit at any time of year.

I highly recommend spending a few days exploring Boston before or after your road trip.

Resources for Exploring Boston: ⚓Essential Things to Do in Boston for First Timers ⚓One Day in Boston: An Itinerary ⚓ Fall in Boston : Where to Go and What to Do

Day 1: Boston MA to North Conway NH

Jump in your car and head out of Boston north toward New Hampshire. Your road trip has begun!

After your scenic drive, arrive in North Conway and check into your cozy lodging. I suggest any of these charming cabins in the White Mountains , many of which are near North Conway, or these Airbnb options .

Drop off your bags and head straight downtown for some exploring.

Check out the charming boutiques, art galleries, and specialty stores that make up North Conway Village. Don’t miss Zeb’s General Store , a local institution since 1990, where you’ll find a classic, old-fashioned general store bursting with unique souvenirs and gourmet goodies.

When hunger strikes, hit up Moat Mountain Smoke House & Brewing Co . for some hearty comfort food and a refreshing craft brew. Enjoy the rustic atmosphere and live music as you unwind from your journey.

Then hit the hay and get ready for another busy day tomorrow.

Resources for exploring North Conway & Nearby: 🍁 15+ Best Things to Do in North Conway NH 🍁 Best Restaurants in North Conway 🍁 15 Fun Things to do in Jackson, New Hampshire

Day 2: North Conway NH

Fuel up with a hearty breakfast at Peach’s Family Restaurant , where the portions are as generous as the smiles.

Of course, it’s fall in the White Mountains: this place is likely to be packed! Go as early as possible to avoid the crowds of other hungry travelers. Now, it’s time to conquer the outdoors! You have a few options today for adventuring in North Conway and the surrounding areas.

• Cathedral Ledge: Consider a hike up Cathedral Ledge in Echo Lake State Park. It’s a relatively short hike that rewards you with breathtaking views of the surrounding valleys and White Mountains.
• Diana’s Baths: Alternatively, opt for the enchanting Diana’s Baths , a series of cascading waterfalls and pools accessible via a family-friendly hike. These look especially lovely surrounded by the New Hampshire foliage
• Black Cap Trail: If you’re looking for a bit more of a challenging hike, tackle the Black Cap Trail , offering panoramic views from the summit.

Later, hop on board on the Conway Scenic Railroad . This vintage-style train offers a leisurely ride through picturesque landscapes, perfect for enjoying the fall foliage from a unique perspective.

The Conway Valley Train is a 55-minute scenic ride, so is ideal for those traveling with kids or who want a quick and cool experience. The railroad also offers longer more extensive fall foliage train journeys. Definitely worth checking out!

In the evening, treat yourself to another delightful dinner at a local favorite or try a new spot for some diverse flavors.

On a past trip to North Conway, my husband and I really enjoyed May Kelly’s Cottage , a tavern serving traditional Irish dishes.

Day 3: Kancamagus Highway to Franconia Notch State Park

Another amazing fall day in the White Mountains awaits you!

Today, you’ll depart North Conway westward along one of New Hampshire’s most iconic roads: the scenic Kancamagus Highway.

Known locally as “the Kanc”, this 56 mile, 2-lane mountain highway (also known as the Kancamagus Scenic Byway ) is particularly breathtaking in the autumn, as the leaves transform into their vibrant splendor.

While you could easily drive the entirety of the Kancamagus in approximately an hour (allow more time in fall), you will absolutely want to take your time.

There are numerous places to stop along the way, including scenic overlooks where you can grab a quick photo or trailheads where you can embark on a hike.

One of the first spots you’ll come across heading out of Conway is Albany Covered Bridge . There is a parking area here (a great opportunity to pay for your $5 White Mountain National Forest day use pass ).

Take one of the trails along the sides of the river to view the bridge, or if you desire, you can climb out onto the large rocks in the river to grab an iconic NH covered bridge photo.

You’ll also definitely will want to stop to check out Sabbaday Falls .

This pretty waterfall can be reached via an easy, flat, well-trodden 0.5 mile hike. It should take about 15 minutes, which makes it a small effort for a big payoff.

After all, there’s nothing like a gorgeous New Hampshire waterfall at the height of fall foliage.

Tips for Driving the Kancamagus in Fall: 🍁This route is popular for good reason, so expect crowds. Take your time driving and watch carefully for pedestrians. 🍁When you stop for photos, etc, make sure you’re in designated parking areas safely off the road. Be aware of the many cars on the highway and stay off the roads when on foot. 🍁Fuel up before leaving North Conway (or Lincoln, if coming from the opposite direction) as there are no gas stations or other amenities along this route.

You’ll have reached the end of the Kancamagus Highway when you arrive in the town of Lincoln . This is a smart place to stop for lunch before continuing on to explore in Franconia Notch State Park.

Franconia Notch State Park

Franconia Notch State Park is one of the crown jewels of the White Mountains. This destination is a testament to the diverse beauty of the Granite State, where rugged peaks, serene lakes, and dense forests come together to create an awe-inspiring landscape that draws thousands of visitors each year.

Head first to the Flume Gorge , an other-wordly natural gorge that features a boardwalk path through towering granite walls and past cascading waterfalls. Add to the scene fall foliage, and you’ve basically entered Tolkien’s Rivendell.

You should allow around 2 hours to explore Flume Gorge in all its winding angles.

Please note there is an entry fee for Flume Gorge, and you’ll save a couple bucks if you book in advance here .

After this busy and active day, you deserve a good meal! I’ve got lots of suggestions in my list of best Lincoln restaurants.

Then it’s time to rest your head.

You will probably love this amazing spot: Lumen Nature Retreat . This is a new glamping site located in nearby North Woodstock, and it’s an ideal place to stay in the fall, right in the heart of nature.

Some of their cozy cabins offer massive windows to look out onto the surrounding trees. Or, you can go even more rustic with tent glamping.

I’ll be staying at Lumen this fall for the first time, and I can’t wait to come back and tell you about it! I’ll definitely be sharing my thoughts here.

Day 4: Franconia Notch to Stowe VT

Get an early start today as you’re off to see Artist’s Bluff, a popular hike that ends in an absolutely spectacular view.

The trail starts in the large dirt parking lot off Rt 18 across the street from Cannon Mountain Ski Resort and heads steeply uphill. While the moderately-rated trail is relatively short, it is steep and robust, with some spots being a bit rocky.

You can expect to be a bit breathless by the time you reach the viewpoint overlooking Echo Lake.

Most hikers recommend starting the trail heading towards Bald Mountain, so tackling the trail clockwise. In the busy fall season, this may be a good option for avoiding the throngs that are heading straight up to the lookout counterclockwise.

Continue to Stowe

Let your GPS guide you on the road trip to Stowe, but try to avoid highways if you can. In my experience, it’s those slower, back roads that give you unexpected, amazing foliage views.

In fact, I’ve seen some incredible foliage along Route 2 near Danville while driving between these two destinations. That is an excellent road to consider taking.

All told, your drive to Stowe will take approximately an hour and a half, without including stops.

Check into your Stowe hotel ( Field Guide is great) and get ready to explore a bit of Stowe’s adorable Main Street.

Welcome to a quintessential New England town, the kind whose image is the subject of countless Vermont postcards and paintings. (In fact, Stowe’s white-steepled Community Church is among the most photographed buildings in Vermont).

As you explore the small, walkable Main Street and side streets, you’ll discover a terrific blend of local businesses that showcase the heart and soul of this picturesque town.

Small art galleries, a cozy coffee shop, an old-fashioned mercantile, and a well-stocked independent bookstore are among the shops you’ll want to visit as you explore downtown Stowe.

Don’t miss Shaw’s General Store, which not only epitomizes the classic New England general store but has done so since 1895!

When dinner hour approaches, head to Doc Pond’s . It’s a laidback restaurant with friendly vibes that is loved by locals and tourists alike. And if you’re staying at Field Guide, it’s just down the road.

Day 5: Stowe VT & Waterbury VT

It’s a beautiful day to take a hike in Stowe! There are numerous hiking trails in the Stowe area to choose from, but for this itinerary I recommend the Sterling Pond trail for a moderate 2 mile hike that ends at a glistening lake.

To get to the trailhead for this hike, you’ll have to drive up Mountain Road and into Smuggler’s Notch. This road becomes very narrow and extremely windy in the heart of the Notch, so while it’s absolutely awesome to check out, be sure to drive slowly and with caution.

And don’t try it with any kind of motorhome or RV!

After your hike, head back in the direction of town and stop at Stowe Mountain Resort. Although there’s no snow this time of year, so skiing is out, you can still enjoy the peaks on a gondola ride!

The famous bright red Stowe Gondola SkyRide takes you to the top of Mount Mansfield, which is the highest peak in Vermont.

The ride up offers splendid views over the colorful trees. Once you’re at the top, grab lunch at The Cliff House or The Waffle, two eatery options.

Now, it wouldn’t be fall in New England if you didn’t add some spookiness into the trip! in the Stowe area, you can visit one of Vermont’s classic covered bridges with a possibly haunted history! Emily’s Bridge, also known as Gold Brook Covered Bridge, is a small covered bridge located on Gold Brook Road, off of Route 100, just south of Stowe village.

According to legend, Emily was supposed to meet her lover at this bridge so they could run away together. But he never showed, and Emily sadly took her own life that night at the bridge. Rumor has it that Emily’s spirit may still haunt the bridge today, and reports of scratches on cars, lights flashing, and other weird happenings just might support that theory. Whether you believe in ghosts or not, this is still a beautiful example of Vermont’s covered bridges and well worth seeing-especially in the fall.

Wind up the rest of your day with a sampling of craft brews and dinner at the Trapp Brewery & Bierhall after enjoying views of Stowe from the grounds at The Trapp Family Lodge. Not in the mood for pretzels, spaetzle, and schnitzel? You might prefer to cozy up at family-owned, classic Italian restaurant Trattoria La Festa . Find more of the top-rated Stowe restaurants here .

More Resources for Exploring Stowe: 🍁 20 Best Things to Do in Stowe Vermont: Local Recs for All Seasons 🍁 15 Gorgeous VRBO & Airbnb Stowe VT Vacation Rentals 🍁 11 Best Hotels in Stowe Vermont: Where to Stay in Stowe

Day 6: Stowe VT to Woodstock VT

Today you’re leaving one gorgeous Vermont small town for another. These two destinations are definitely my top recommendations for visitors to the Green Mountain State. The road trip from Stowe to Woodstock is a fairly short one distance-wise, but you can make sure to capture the best possible foliage views by taking Route 100 south. There are also 2 essential places to stop along the way.

The first stop is the Cold Hollow Cider Mill , a Vermont fall necessity that you’re going to absolutely love.

This is THE spot for apple cider donuts, the best food on the planet, and truly the staple of my autumn diet. But not only is Cold Hollow the go-to for apple treats, it’s also a well-stocked, adorable country store, a tasty restaurant, and a hard cider tasting room.

Your second stop is the Ben & Jerry’s Factory . Their ice cream is world famous. Not only because it is delicious but because the company is known for championing progressive causes.

The factory tour is quite fun and it smells amazing in there! After you learn how Cherry Garcia and other favorite flavors are made, you can pay homage to flavors long gone in the “Flavor Graveyard” on a nearby hill. Does anyone remember Magic Brownies?

If you’ve got room left for lunch, grab some, and then continue on to Woodstock.

Once in Woodstock, check into your lodging. The Woodstock Inn is the perfect luxury choice, while The Shire is a solid mid-range option. Both are right downtown. Next, get ready for some pleasant exploring.

Stroll the downtown and the wide village green, which has a covered bridge just steps away. Browse the collection of shops with a wide variety of goods, and don’t miss Gillingham’s, the oldest general store in Vermont. As the afternoon continues, choose a local farm to visit. Billings Farm is a historic working dairy farm where you can learn a lot about the animals and enjoy the surrounding property. Sugarbush Farm is a 4-generation family farm specializing in cheese and maple syrup.

Both farms are terrific, and fortunately, Woodstock is small enough that you can likely squeeze both into your itinerary!

Dinner in Woodstock ends your day, and there are so many great restaurant options .

If you schedule well in advance, Cloudland Farm , is a true farm-to-table experience out of this world. The menu changes daily and everything is crafted completely from scratch for the most memorable Vermont culinary journey.

More Resources for Exploring Woodstock: 🍁 20 Best Things to Do in Woodstock, Vermont 🍁 10 Best Hotels in Woodstock VT: Where to Stay in 2023 🍁 These 12 Restaurants in Woodstock Vermont NEED to Be on Your List

Day 7: Woodstock VT to Boston MA

It’s the final day of your incredible fall road trip around New England. The last leg of the journey takes you back to Boston.

Before departing Woodstock, grab coffee and a scrumptious breakfast at Mon Vert Cafe. I recommend my personal go-to: the maple latte.

Need some suggestions for road trip entertainment? You could grab one of these New England books in audio format on Audible and listen to something oh-so-appropriate for the journey.

8 or 9 Day New England Fall Road Trip Itinerary

If you’ve got an extra day or two to explore New England, you should add Salem, Massachusetts to your trip.

Because it’s such an awesome town, it’s incredibly busy in the fall. I repeat, incredibly busy .

But if you’re on a once-in-a-lifetime New England trip, you don’t want to miss this iconic spot. I get it.

Visiting Salem in the month of October is classic and so very atmospheric. My best tip for traveling to Salem is to book your lodging well in advance of this popular season and also start each day as early as possible.

The crowds can get crazy in Salem in the fall, but a 7am start gives you an hour or two for some quiet exploring (and some nice photos of the town!)

10 Day New England Fall Road Trip Itinerary

This 10 day itinerary for New England in the fall contains all of the same destinations as the 7 day itinerary, but your first stop instead will be Acadia National Park in Maine .

If you’ve got 10 days to spend exploring New England, adding a coastal stop is an absolute must. Not only is fall a fabulous and beautiful time to visit Acadia, it also tends to be somewhat less busy during this time than in the summer months. Check out all of our resources on things to do in Acadia and nearby Bar Harbor here:

5 Day New England Fall Road Trip Itinerary

Need to shorten your road trip? For a 5 day trip, consider removing either Stowe or Woodstock from the itinerary. While both are spectacular destinations, this is the easiest way to shorten your trip.

Best Fall Foliage Drives in New England

Looking for some shorter New England fall road trip routes? There are a number of scenic fall foliage drives to consider, that can be done in just a few hours or stretched into several days.

Newport’s Ocean Drive – Rhode Island

• Distance: 10 miles
• Start and End: Fort Adams Park to Bellevue Ave
• Best Time to Go: September to Early November

I love Newport , period. This charming seaside city, located on Aquidneck Island in Rhode Island, is like an extravagant window to the past. Gilded Age mansions such as The Breakers are found all over this town, and the 19th century echoes of wealthy, lavish resort living are as strong today as they were then. 

Fall in Newport provides some great opportunities.

The summer’s peak of tourism has passed, and with it comes a refreshing ocean breeze among the colorful trees that surround mansion estates and scenic parks.

Since the fall foliage is nice, but not the primary factor for your fall road trip to Rhode Island, you can enjoy Newport anytime between September and early November.

Ocean Drive is a 10-mile seaside drive that follows the southern shore of Newport. It is not only one of the loveliest New England scenic drives as it follows along the ocean, but it’s also the perfect route for accessing all the best of Newport.

We think Fort Adams Park is a great place to start your trip! Continue from here to Brenton Cove Shore, where you’ll find the New York Yacht Club. After this, you’ll want to check out Castle Hill’s historical lighthouse in the East Passage of Narragansett Bay. 

Then spend some time relaxing at Brenton Point State Park , one of the major highlights on Ocean Drive. This wide-open green space on the south end of the island, with vast ocean views, is the perfect spot to relax, have a picnic, or go fishing.

Continue past various beaches and scenic outlooks to Bellevue Ave, where you will discover a majority of the lavish 19th century mansions. The Breakers , Marble House , Rough Point , and the Elms are a few of the best. Take a walking tour and learn all about the history of these extravagant homes.

Points of Interest:

• New York Yacht Club
• Castle Hill Lighthouse
• Brenton Point State Park
• Fort Adams Park
• The Breakers
• Marble House
• Rough Point
• The Red Parrot Restaurant

Park Loop Road in Acadia National Park – Maine

• Distance: 27 miles
• Start and End: Hulls Cove Visitor Center to Cadillac Mountain
• Best Time to Go: September to Early October

Acadia National Park in Maine is somewhat of an unsung national park hero.

While people are busy praising the glory of Yellowstone and Yosemite, Acadia continues to stand its ground on the list of top 10 most visited national parks in the U.S!

And for good reason. Camping in the forest by wetlands near the craggy seaside, extensive biking and hiking trails, large ponds and lakes, rocky beaches, and all the best fall foliage is right at your fingertips.

Seaside towns like Bar Harbor also bring a lot of ease and convenience to an adventure-driven destination. 

To get the most enjoyment out of your fall trip, we’d recommend going in September before the temperatures drop significantly; the leaves will be changing, and the crowds will be light at this time!

We think Park Loop Road is the prime route to explore all of Acadia’s best adventures and natural beauty, especially during fall.

This 27-mile, mostly one-way scenic road takes you around the east side of Mount Desert Island. Get oriented at Hulls Cove Visitor Center near Bar Harbor with a map of the island.

Then drive on at your own pace, hitting Sand Beach, the uber-popular Thunder Hole, and Otter Cliffs. A major highlight you will also not want to miss is Bass Harbor Head Lighthouse .

Further along the route is Sieur-de-Monts , where you can explore the Nature Center and Wild Gardens of Acadia.

Then head to Jordan Pond and Jordan Pond House , where you can learn the history of its important cultural legacy and hike the pond’s loop along meandering boardwalks and native wildlife.

End your national park road trip in Maine by driving to the summit of Cadillac Mountain, the perfect spot to catch an amazing autumn sunset.

Points of Interest: 

• Hulls Cove Visitor Center – Bar Harbor 
• Shore Path – Bar Harbor
• Bass Harbor Head Lighthouse – Bass Harbor
• Sand Beach – Bar Harbor
• Thunder Hole – Bar Harbor
• Otter Cliffs – Mount Desert Island
• Sieur-de-Monts – Bar Harbor
• Jordan Pond, Jordan Pond House – Seal Harbor
• Cadillac Mountain – Mount Desert Island

Vermont’s Scenic Route 100 – Vermont

• Distance: 150 miles
• Start and End: Wilmington to Stowe
• Best Time to Go: September to Mid-October

Looking for that quintessential “fall in New England” experience?

You know, the one you see in movies with red barns and grazing cows, an endless expanse of green hills, orange and yellow maple trees, and locally owned shops and artisan fairs?

Well, you’re going to want to put on some cozy plaid, a beanie, and take a cruise up Vermont’s Scenic Route 100 , undoubtedly one of the best fall foliage drives in New England.

In fact, it’s one of my favorite Vermont fall road trip routes!

Vermont’s Route 100 is a winding, scenic road that traverses north for 200 miles from the border of Massachusetts to Lake Memphremagog, along the east side of Green Mountain National Forest.

Dubbed by Yankee Magazine as the best foliage drive in VT (and definitely one of the best in New England!), the variety of landscapes, points of interest, and peak foliage views are unbeatable. 

Start your journey in Wilmington , a quaint farming community with a historical downtown.

Then move north toward Weston, a stretch of highway featuring wildflower fields and cute gazebos.

Stop at the Vermont Country Store for one-of-a-kind handmade goods.

Continuing north, you will pass by beloved local landmarks like Echo Lake State Park and Lake Rescue.

And just above Amherst Lake is Plymouth, the perfect place for history buffs to explore the President Calvin Coolidge State Historic Site , the homestead Coolidge grew up on. 

Further north still, you’ll enjoy a 10-mile stretch of densely forested highway along the Granville Gulf State Reservation. Keep an eye out for moose and rushing rivers as you carry on toward the Mad River Valley.

This region has become a popular destination due to the area’s chic vibe, killer ski resorts like Killington and Sugarbush, and craft fairs, music festivals, and covered bridges abound.

You’ve almost arrived at the end, so why not indulge in a little Ben & Jerry’s ? Waterbury is home to the Vermont-based ice cream company we all know and love. Take a factory tour and sample some of the quirky flavors!

Last but not least, end your road trip in Stowe, a Vermont town classic with all the fixings. It’s a white-steeple church, ski bum, beer brewing, local artisan kind of village, and the perfect place to lay your head after a long New England fall foliage drive!

• Downtown Wilmington – Wilmington
• Vermont Country Store – Weston 
• Echo Lake, Lake Rescue, Amherst Lake 
• President Calvin Coolidge State Historic Site – Plymouth
• Granville Gulf State Reservation – Granville
• Killington Ski Area – Killington
• Sugarbush Resort – Warren
• Ben & Jerry’s Factory – Waterbury
• Stowe Village – Stowe

The Lake Winnipesaukee Loop – New Hampshire

• Distance: 100 miles
• Start and End: Alton

Who doesn’t love a good loop route? There’s just something satisfying about perpetually seeing new sights for the entire adventure, without the backtracking.

The route around Lake Winnipesaukee in the Lakes Region of New Hampshire is the perfect New England fall road trip itinerary. With 8 unique towns bordering NH’s largest and most popular body of water, you’ll discover the ideal blend of outdoor activities and luxury lake living during the cooler, slower months. 

In reality, you can start your journey in any one of these towns and follow the lake’s edge in whichever direction your heart desires. But we think Alton – a historical bay town with a beautiful 4-mile cove – is a great place to begin (and end!).

After taking in the views from their cozy cove, head on to Wolfeboro , a crunchy lake town with its own rail trail and an outdoor art walk. In addition, Wolfeboro’s Wright Museum of World War II is a fantastic educational institution dedicated to World War II history.

And if you’re looking for a souvenir to remember your trip, stop by Black’s Paper Shop for a special gift. 

From Wolfeboro, drive on to Moultonborough, one of the oldest incorporated towns in the U.S. This charming town was founded in 1777 and has some amazing gems, especially the Old Country Store , which is considered the oldest surviving business and general store in the country!

Waste all your pennies at the candy counter, sample unique local foods, or buy some handcrafted home goods. Another gem in Moultonborough is Castle in the Clouds , a magnificent mansion high up in the hills where you can tour the grand estate and learn about the history of its original owners.

Next stop on the loop is Meredith , a central hub of the tourism, luxury lake living, and resort leisure that Lake Winni attracts. In this scenic town, you might find yourself ogling at the grand lake houses and stylish hotels lining the bay.

Pull off the highway and shop your heart out at Mill Falls Marketplace , an open-air shopping center with restaurants, a bookshop, Ben & Jerry’s, and chic indie businesses.

Meredith is a great halfway point to spend the night if the 100-mile loop is too much.

If not, carry on to Laconia while the sun is still shining. If the weather permits, visit Weirs Beach .

If not, visit Funspot , a massive entertainment center that boasts the record for Largest Arcade in the World.

Then Gilford comes next on the loop.

The biggest draw this town sees is to Gunstock Resort , which can be hiked during the off-ski season. And finally, you will arrive back in Alton to complete your epic Lake Winnipesaukee road trip.

We love the lake life, especially on a scenic fall foliage drive!

• Alton Bay – Alton
• Wolfeboro Art Walk – Wolfeboro
• The Wright Museum of World War II – Wolfeboro
• Black’s Paper Shop – Wolfeboro
• The Old Country Store – Moultonborough
• Castle in the Clouds – Moultonborough
• Mill Falls Marketplace – Meredith
• Weirs Beach – Laconia
• Funspot – Laconia
• Gunstock Resort – Gilford

U.S. Coastal Route 1 – Maine

• Distance: 200 miles
• Start and End: Kennebunkport to Bar Harbor
• Best Time to Go: Mid-September to Early November

We all need a little more Maine in our lives, and that’s why we felt like our Acadia Loop road trip wasn’t quite enough – so we’re throwing U.S. Coastal Route 1 into the mix!

This incredible, north-south coastal highway actually starts all the way down in Key West, and traverses 2,390 miles up the east coast to Fort Kent in Maine. 

Maine’s portion of the U.S.’ very first north-south highway system is over 200 miles of pure natural beauty. Crossing through peaceful boating towns, beachside cities, and craggy coastal landmarks, you’ll have the best of Maine’s attractions and fall foliage without all the summer traffic. 

A great place to kick things off is in Kennebunkport , a charming southern Maine beach town.

Walk around the sandy Goose Rocks Beach, then get a good look at a collection of historical streetcars at the Seashore Trolley Museum .

As you continue north through Biddeford and Old Orchard Beach, stop at one of New England’s most iconic landmarks: the Portland Head Light on Cape Elizabeth. This iconic white lighthouse was built in 1791, making it the oldest lighthouse in Maine. 

From here, you’re just a hop, skip, and jump away from Portland , one of the friendliest, “foodiest,” artsiest towns on the East Coast. If you spent an extra day or five here, you wouldn’t regret it. Well, you might regret gorging on copious amounts of Holy Donuts and Duckfat French fries, but that’s a different story. 

Beyond Portland, you’ll pass through Georgetown, Brunswick, and arrive in Rockland .

This small seaside town has lovely harbor views, a charming downtown, and great food to boot. Check out the Farnsworth Art Museum or Archipelago to satisfy your craving for fine art. And if you are in the mood for brunch, dine at the cheerful Home Kitchen Cafe . 

We are on the home stretch now!

A great destination to end your Coastal Route 1 road trip is none other than Bar Harbor, situated on Mount Desert Island in Acadia National Park. Bar Harbor is insanely busy in the summer months but gets a bit sleepier and much more relaxing in September and October. Bar Harbor is a souvenir-hunter’s haven, as well as an adorable, quaint town to walk around and enjoy harbor views from Shore Path.

Not to mention, Bar Harbor gives you incredible access to everything Acadia National Park has to offer.

• Goose Rocks Beach – Kennebunkport
• Seashore Trolley Museum – Kennebunkport
• Portland Head Light – Cape Elizabeth
• The Holy Donut – Portland
• Duckfat – Portland
• Farnsworth Art Museum – Rockland
• Archipelago – Rockland
• Home Kitchen Cafe – Rockland

The Berkshires – Massachusetts

• Distance: 35 miles
• Start and End: Stockbridge to Williamstown
• Best Time to Go: Early September to Late October

Our list of fantastic road trips in New England wouldn’t be complete without including New England’s most historical, highly educated, and diverse state: Massachusetts .

While there are many wonderful regions to explore in MA – from the Cape Cod coastline to bustling Boston – we think there is something so special about the Berkshires.

The Berkshires is a collection of towns in the rolling highlands of western MA.

The area’s pastoral beauty is matched only by its cultural and artistic sophistication. If you are looking for a scenic countryside retreat with plenty of opportunities for historical exploration, leisurely driving, and prime New England fall foliage drives, this is the destination for you.

Start off strong in the town of Stockbridge , where you will find some incredible natural and historical gems.

Explore the Norman Rockwell Museum , housing works by this famous American painter in the very place he spent the last 25 years of his life.

Then pop over to the Berkshire Botanical Garden , which highlights native plants that thrive in the Berkshires. Then continue north for 10 minutes on Route 7 to arrive in Lenox, a town best known for being the former home of author Edith Wharton. 

After touring The Mount , Wharton’s gorgeous estate, head to Pittsfield, yet another town known as the home of a reputable author (seriously – we should just call this the legendary American authors tour).

If you appreciate literature, take a tour of Arrowhead House , the home where novelist Herman Melville wrote Moby Dick. While you are still in Pittsfield, check out the Berkshire Museum , which exhibits a cool mishmash of art, natural history, and ancient civilization.

From Pittsfield, another historical institution awaits you in Hancock at the Hancock Shaker Village .

And after you move along from Hancock and pass through Lanesborough, you’ll end up in North Adams , a historic college and mill town with a strong arts vibe and hiking access to Mount Greylock, the highest peak in MA.

Check out the Mass Museum of Contemporary Art while you’re here. 

Finally, end your Berkshires road trip in Williamstown, a cultural and educational hub in the Berkshires.

This beautiful, “quintessential Berkshire village” is surrounded by mountains, biking and hiking trails, and farmlands. Williams College is the heart of the town, imbuing it with a flourishing arts and culture scene.

Fall in Massachusetts is heavenly, so you’ll find plenty to do and see during a Bay State fall foliage road trip!

• Norman Rockwell Museum – Stockbridge
• Berkshire Botanical Garden – Stockbridge
• The Mount, Edith Wharton House – Lenox
• Arrowhead House – Pittsfield
• Berkshire Museum – Pittsfield
• Hancock Shaker Village – Hancock
• Mount Greylock – North Adams
• Massachusetts Museum of Contemporary Art – North Adams
• Williams College – Williamstown

Connecticut State Route 169 – Connecticut

• Distance: 47.3 miles
• Start and End: Lisbon to Woodstock

We’re topping off our list of New England fall road trips with Connecticut State Route 169 , a National Scenic Byway featuring all the historic buildings, charming communities, and autumn colors that make New England so memorable.

Connecticut is the third smallest state in the nation, but it’s got a lot going for it as the home of Mystic Seaport, the Mark Twain house, the mighty Connecticut River, and Yale University. 

Starting in eastern Connecticut in the town of Lisbon and moving north to Woodstock near the border of Massachusetts,

Route 169 offers a drive through living history. Start your tour in Lisbon with a foliage stroll through Lisbon Meadows Park.

Then head north on 169 to Waterbury, where you can visit the Prudence Crandall Museum or chill on the Waterbury Green at the city’s center. 

Not much further north you will hit the town of Brooklyn, home to the New England Center of Contemporary Art.

Pay attention to the unique architecture as you meander onward to Pomfret, a town with incredible history that you can observe in the beautiful 19th century churches, homes, and libraries.

Your final destination on the Route 169 tour is the town of Woodstock, a mere 10 minutes north of Pomfret. While here, you can’t miss out on the Roseland Cottage , a historic 1846 house-turned-museum.

This signature Gothic Revival home with its bold pink exterior was once the summer home of the Bowens, one of Connecticut’s prominent Victorian Era families. Explore its ornate, patterned, vibrant rooms and learn about a unique piece of Connecticut history.

• Lisbon Meadows Park – Lisbon
• Prudence Crandall Museum – Waterbury
• Waterbury Green – Waterbury
• New England Center of Contemporary Art – Brooklyn
• Roseland Cottage – Woodstock

No matter how long you explore New England’s 6 amazing states for, I hope you have an incredible adventure in this region I love so much!

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Ultimate 10-Day Coastal New England Road Trip Itinerary

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The coast of New England is the perfect destination for a summer or fall road trip, with plenty to see, do, eat, and explore!

New England is part of the northeastern United States and includes six states—Maine, Vermont, New Hampshire, Massachusetts, Connecticut, and Rhode Island. Most of the major cities in these states fall along the Atlantic Coast, including Boston, Newport, and Portland, making the New England coast the perfect destination for a road trip!

This ten-day coastal New England road trip itinerary includes stops in Massachusetts, Rhode Island, New Hampshire, and Maine. Here’s a look at the best things to do, where to stay, and what to eat during your New England road trip.

Disclosure: Some of the links in this blog post are affiliate links, meaning that I earn a commission if you click through and make a purchase at no additional cost to you. This helps me keep the content on my website free for you to enjoy!

When Is the Best Time to Go on a New England Road Trip ?

When planning your New England road trip itinerary, it’s important to consider that the weather in New England can get chilly, icy, and snowy—especially during the winter and early spring months.

Traveling between June and August is your best bet if you want to enjoy the water activities along New England’s coast. If you prefer to avoid summer tourists, traveling to New England between September and November offers an excellent opportunity to see the beautiful fall leaves!

We took our trip at the end of September and the start of October. While the weather was still relatively warm in most places, we could watch the beginning of fall peek out in some of the northern states, like New Hampshire and Maine!

Where Should I Fly Into to Start & End My New England Road Trip?

This New England road trip itinerary starts and ends at the Boston Logan International Airport .

I highly recommend flying to and from the Boston Logan International Airport for your New England road trip itinerary. This airport is by far the largest in New England, so you’ll likely be able to find the cheapest roundtrip flights. Plus, there isn’t anywhere on this itinerary that is more than a three-hour drive from Boston, so it’s a great “home base” for your trip.

Recommended Coastal New England Road Trip Itinerary

Boston, m assachusetts.

Fly into the Boston Logan International Airport to check off the first stop on your New England road trip itinerary!

Boston is filled with tons of history, great food, and plenty of places to explore! Although this New England road trip itinerary calls for three days in Boston, if you have time to extend your trip, I’d recommend spending a few extra days here to see all the city has to offer!

Boston, Massachusetts, is the perfect place to begin your New England road trip itinerary because there is so much to see, do, and discover. Plus, you won’t need a car for your time in the city, so you can forgo the car rental and begin exploring as soon as your plane touches down! Fortunately, Downtown Boston is only a ten-minute drive from the airport, so your Uber or Lyft ride to your hotel won’t be too expensive.

Top Things to See and Do in Boston

• Walk the Freedom Trail to see the sights that shaped the American Revolution (you can take a self-guided tour or go on guided tour ).
• Play a part in the Boston Tea Party at the Boston Tea Party Ships and Museums.
• Try the most authentic Italian food in Boston on a North End Boston Food Tour .
• Stroll around and see the flowers, lakes, statues, and monuments in the Boston Public Garden.
• Snap a picture of the most photographed street in America— Acorn Street !
• Marvel at the incredible architecture of the Boston Public Library.
• Explore Eataly Boston to shop for local Italian goods, dine at unique restaurants, and more!
• Cheer on the Red Sox at the historic and iconic Fenway Park (or take a one-hour tour !) .

Top Places to Eat in Boston

• Try a lobster roll or bowl of clam chowder at the oldest restaurant in Boston established in 1826—the Union Oyster House .
• Enjoy a Boston Cream Pie (and Boston Cream Pie Martini!) at the Omni Parker House.
• Sit down for a delicious brunch at Tatte Bakery and Café , a popular local chain.
• Marvel at the spectacular views with a drink in hand at the Lookout Rooftop & Bar.
• Sample an authentic cannoli in Boston’s North End at Mike’s Pastry.
• Eat some carbonara at MIDA , a local Italian restaurant with a modern twist.
• Channel your inner New Englander and eat a donut from Kane’s Donuts!
• Order a coffee and HUGE croissant from the Tradesman Coffee Shop & Lounge .

Where to Stay in Boston

• The Godfrey Hotel Boston: Enjoy extremely spacious rooms at this beautiful hotel, located just a short walk away from the Boston Common, Boston Public Garden, and Brattle Book Shop.
• Hyatt Centric Faneuil Hall Boston: Located in the heart of Boston, this affordable hotel is located near the Boston Tea Party Ships & Museum, Quincey Market, Faneuil Hall, and other sites along the Freedom Trail.
• The Newbury Boston: Relax at this hotel’s luxury bar and restaurant or order room service after a busy day of exploring the city.

Read More on Boston

• 26 Best Things to Do in Boston
• Complete Guide to the Freedom Trail
• 12 Best Day Trips from Boston

Plymouth, M assachusetts

On the fourth day of your trip, head to the Boston Logan International airport to pick up your car rental, and then head to Plymouth, just over a one-hour drive from the city. I’d recommend enjoying an entire day here but making your way to Newport, the next stop on the itinerary, to spend the night!

Plymouth is endearingly known as “America’s Hometown” because this city is where the Pilgrims arrived on the Mayflower in 1620. Here, you will be able to immerse yourself in fascinating history at museums, monuments, and more. Plymouth definitely deserves a spot on your New England road trip itinerary!

Top Things to See and Do in Plymouth

• Tour the Plimoth Patuxet Museums to travel back in time with their four main attractions: the  Historic Patuxet ,  English Village ,  Mayflower II , and the  Plimoth Grist Mill .
• See Plymouth Rock —marking the location where the Pilgrims landed in 1620!
• Tour the Howland House —the oldest (and only!) standing structure in Plymouth where the Pilgrims actually lived.
• Visit the Pilgrim Hall Museum to see artifacts and exhibits about the history and life of the Pilgrims.
• Take a stroll through the beautiful Brewster Garden .
• If you’re visiting in October, travel south for the Cranberry Harvest Festival !

Top Places to Eat in Plymouth

• Sample some local wines at the Plymouth Bay Winery .
• Enjoy some authentic pizzas, pasta, and other Italian fare on the scenic waterfront at Mamma Mia’s of Plymouth Waterfront .
• Try oysters and other meals from the raw bar at Salt .

Read More on Plymouth

• 10+ Best Things to Do in Plymouth for History Lovers

Newport, R hode Island

After your day in Plymouth, head to Newport, Rhode Island. Newport is a coastal town that visitors love for its beautiful beaches, stunning mansions, and great seafood. While Newport is gorgeous at all times of the year, it shines in the summer!

Top Things to See and Do in Newport

• Take a stroll along the Cliff Walk , a 3.5-mile pathway along the coast that offers beautiful views of the Atlantic Ocean and the city’s luxurious mansions.
• Shop and dine along Bellevue Avenue or Thames Street, two of the most popular streets in Newport.
• Go wine tasting at Greenvale Vineyards for scenic views, jazz music, and great wine!
• Tour the Newport Mansions , like The Breakers, The Elms, or Marble House. You can also book this Newport Gided Age Mansions Trolley Tour that includes admisson to The Breakers!
• Explore Bowen’s Wharf or take a boat ride or cruise from Long Wharf.
• Relax on Easton Beach , also known as “First Beach”.

Top Places to Eat in Newport

• Enjoy locally-roasted coffee and a light breakfast from The Nitro Bar.
• Savor generous breakfast portions and a charming atmosphere at CRU Café.
• Hang out at the Brick Alley Pub & Restaurant while enjoying seafood, steaks, and a local beer.
• Make reservations at The Mooring Seafood Kitchen & Bar for an upscale seafood dinner and spectacular harbor views.
• Try authentic handmade pizza, pasta, calzones, and more at Pasta Beach.
• End the night with an ice cream cone from Kilwin’s Chocolates and Ice Cream.

Where to Stay in Newport

• Hammetts Hotel: Stay in a charming boutique hotel with nautical-themed décor, modern architecture, and clean rooms with close access to Bowen’s Wharf and Thames Street.
• The Newport Harbor Hotel & Marina: Have fun at this popular waterfront hotel in Newport with a seafood restaurant, indoor pool, beautiful marina, and other fabulous amenities.
• Newport Marriott: Enjoy a luxury stay with exceptional views of Long Wharf at this hotel with a stunning lobby, indoor pool, and relaxing spa.

Read More on Newport

• How to Spend a Charming Weekend in Newport
• 10 Best Places to Eat in Newport
• 11 Best Luxury Hotels in Newport, Rhode Island

Portsmouth, N ew Hampshire

After a few days in Newport, it’s time to head north again, to New Hampshire! I’d recommend leaving Newport as early as possible on the seventh day of your trip to spend as much of the day in Portsmouth as possible.

Portsmouth is a picturesque town along New Hampshire’s narrow coastline with a rich naval history and beautifully preserved buildings. It’s also cozy, especially in the fall, so it’s the perfect place to spend one quaint, relaxing day!

After spending the day in Portsmouth, you can either stay the night or drive up to Portland, Maine, to spend the night. Either option works with this New England road trip itinerary!

Top Things to See and Do in Portsmouth

• Immerse yourself in over 300 years of history at the Strawberry Banke Museum.
• Spend time shopping, dining, and exploring Market Square.
• Snap a picture of the picturesque North Church of Portsmouth
• Stroll down the Black Heritage Trail to discover historically significant locations meant to share information about Black life in early America.
• Frolic in the beautiful flowers in Prescott Park overlooking the Piscataqua River and the Portsmouth Naval Shipyard.

Top Places to Eat in Portsmouth

• Enjoy a woodfired flatbread pizza at Flatbread Company , complete with a cozy environment!
• Grab a local beer and a burger (or French Onion Soup!) at the Thirsty Moose Taproom.
• Make reservations for an upscale dinner at Cava Tapas & Wine Bar.
• Visit Book & Board —a bookstore converted into a quaint eatery and pub.
• Enjoy some tea and popovers at Popovers on the Square .

Where to Stay in Portsmouth

• Residence Inn by Marriott Portsmouth Downtown: Enjoy spacious, modern suites equipped with a kitchen, seating area, and comfortable beds.
• The INN Downtown: Experience close access to the city’s best attractions in the cozy boutique studio apartments in Downtown Portsmouth.
• The Hotel Portsmouth: Stay in a charming historic home converted into a hotel in Market Square (bonus: continental breakfast!).

Read More on Portsmouth

• How to Spend the Perfect Day in Portsmouth

Portland, Maine

The last stop on our New England road trip itinerary is Portland, Maine. Portland is home to beautiful coastal views, craft beer, great seafood, and lighthouses galore. If any of those things are up your alley, you’ll love Portland!

Although this New England road trip itinerary says you’ll spend three days in Portland, it will actually be closer to two and a half. You’ll need at least half a day to drive back to Boston to board your flight home!

Top Things to See and Do in Portland

• Visit Fort Williams Park for scenic sites and attractions, including the most photographed lighthouse in America—the Portland Head Light .
• Go on a brewery tour to local craft breweries, like Allagash Brewing Company , Foundation Brewing Company , and more.
• Walk around Old Port and shop at the local boutiques and specialty stores.
• While you’re in Old Port, embark on an Old Port Culinary Walking Tour from Portland to sample Maine-inspired cuisine.
• Marvel at the views at sunset along the Eastern Promenade .
• Grab a drink at Lincoln’s —a hidden speakeasy in Old Port (hint: look for the double red doors on Market Street).
• Go on a cruise, whale watching tour, or sea kayaking tour from in Casco Bay .

Top Places to Eat in Portland

• Try a potato donut (or two…. or three….) at the Holy Donut .
• Head to Duckfat for some hand-cut Belgian fries and homemade dipping sauces.
• Dine at Luke’s Lobster on the Portland Pier, and watch the fresh “catches of the day” be unloaded onto the dock while you eat.
• Make reservations for an upscale dinner at Eventide Oyster Company .
• Grab a slice of pizza and other Italian-style street food at Slab Sicilian Street Food .

Where to Stay in Portland

• Portland Regency Hotel & Spa —Enjoy a luxurious, romantic stay in the heart of Old Port to be near all the city’s most popular locations.
• The Press Hotel, Autograph Collection —Also located in Downtown Portland, this hotel has beautiful interiors and awesome amenities and is close to many of the best things to do in the city.
• Tru By Hilton Portland Airport —This hotel is just outside the city and offers close access to the airport, comfortable rooms, and a complimentary breakfast.

Read More on Portland

• 10 Best Things to Do in Portland
• 4 Best Breweries in Portland

Let’s Hit the Road!

And unfortunately, that marks the end of your New England road trip itinerary. However, if you follow this New England road trip itinerary, you’re bound to have a fantastic time!

Which of these stops would be your favorite? Let me know in the comments below!

Pin This 10-Day Coastal New England Road Trip Itinerary for Later!

About the Author

Brittany Sawyer

Hi, I'm Brit! I'm a writer from Phoenix, AZ who loves coffee, golden retriever puppies, and obviously, travel! I help ordinary women (like me!) dream, plan, and do extraordinary travel experiences.

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The perfect New England fall-foliage road trip for 2023

Oct 2, 2023 • 7 min read

On this 424-mile drive through New England, the foliage will dazzle © Chun Chen / 500px / Getty Images

Touring New England in search of autumn’s changing colors has become so popular it has grenerated its own subculture of “leaf-peepers.”

While admiring the leaves during foliage season is possible everywhere in the the region, here’s one road trip that will immerse you in the best of those glorious colors.

New England’s best fall-foliage road trip

Trip length : 5– 7 days; 424 miles (682km) Best time to go : Late September to mid-October Essential photo : Kent Falls set against a backdrop of autumnal colors Top experience : Zip-lining through the tree canopy in Bretton Woods

Scarlet and sugar maples, ashes, birches, beeches, dogwoods, tulip trees, oaks and sassafras all contribute to the carnival of autumn color in New England. But this trip is about much more than just flora and fauna: expect to embrace the harvest spirit makes at family outings at pick-your-own farms, leisurely walks along dappled trails and tables groaning beneath delicious seasonal produce.

1. Lake Candlewood, Connecticut 

With a surface area of 8.4 sq miles, Candlewood is the largest lake in  Connecticut . On its western shore,  Squantz Pond State Park is popular with leaf-peepers who come to amble along the pretty shoreline. In Brookfield and Sherman, quiet vineyards with acres of gnarled grapevines line the hillsides; at  White Silo Farm Winery , the focus is on specialty wines made from farm-grown fruit. For the ultimate bird’s-eye view of the foliage, consider a late afternoon hot-air balloon ride with GONE Ballooning  in nearby Southbury.

The drive: From Danbury at the southern tip of the lake, you have a choice of heading north via US 7, taking in Brookfield and New Milford (or trailing the scenic eastern shoreline along Candlewood Lake Rd S); or heading north along CT 37 and CT 39 via New Fairfield, Squantz Pond and Sherman, before reconnecting with US 7 to Kent.

2. Kent,  Connecticut

Picturesque Kent ranks among the top spots for fall foliage in all of New England. Situated in the Litchfield Hills on the banks of the Housatonic River, the village is surrounded by dense woodlands. For a sweeping view, hike up Cobble Mountain in Macedonia Brook State Park , a wooded oasis two miles north of town. The steep climb to the rocky ridge affords panoramic views of the foliage against a backdrop of the Taconic and Catskill mountain ranges.

The 2175-mile (3500km) Georgia-to-Maine  Appalachian National Scenic Trail  also runs through Kent and up to Salisbury, on the Massachusetts  border. Unlike much of the trail, the Kent section offers a mostly flat five-mile walk alongside the Housatonic, the longest river walk of the entire trail. The trailhead is accessed on River Rd, off CT 341.

The drive:  The 15-mile drive from Kent to Housatonic Meadows State Park along US 7 is one of the most scenic drives in Connecticut. The single-lane road dips and weaves between thick forests, past Kent Falls State Park  (with its tumbling waterfall, visible from the road) and over West Cornwall’s picturesque covered bridge, which spans the Housatonic.

3. Housatonic Meadows State Park, Connecticut

During the spring thaw, the churning waters of the Housatonic challenge kayakers and canoers. By summer, the scenic waterway transforms into a lazy, flat river perfect for fly-fishing. In the Housatonic Meadows State Park, campers vie for a spot on the banks of the river while hikers take to the hills on the Appalachian Trail. Housatonic River Outfitters runs guided fishing trips with gourmet picnics.

Popular with artists and photographers, one of the most photographed fall spots is the Cornwall Bridge (West Cornwall), an antique span that stretches across the broad river, framed by vibrantly colored foliage.

The drive:  Continue north along US 7 toward the Massachusetts border and Great Barrington. After a few miles, you’ll leave the forested slopes of the park behind you and enter expansive rolling countryside dotted with large red-and-white barns. Look out for hand-painted signs advertising farm produce – and consider stopping overnight in Falls Village, which has an excellent B&B.

4. The Berkshires,  Massachusetts

Blanketing the westernmost part of Massachusetts, the rounded mountains of the Berkshires turn crimson and gold as early as mid-September. The effective capital of the Berkshires is Great Barrington, a formerly industrial town whose streets are now lined with art galleries and upscale restaurants.

It’s the perfect place to pack your picnic or rest your legs before or after a hike in the nearby Beartown State Forest . Crisscrossing its 12,000 acres, hiking trails yield spectacular views of wooded hillsides and pretty Benedict Pond. Further north, October Mountain State Forest is the state’s largest tract of green space (16,127 acres), also with ample hiking trails. The name – attributed to Herman Melville – gives a good indication of when this park is at its loveliest, with its multicolored tapestry of hemlocks, birches and oaks.

The drive:  Drive north on US 7, the spine of the Berkshires, cruising through Great Barrington and Stockbridge. In Lee, the highway merges with scenic US 20, from where you can access October Mtn. Continue 16 miles north through Lenox and Pittsfield to Lanesborough. Turn right on N Main St and follow the signs to the park entrance.

5. Mt Greylock State Forest,  Massachusetts

Massachusetts’ highest peak is not so high (only 3491ft / 1064m) – yet a climb up the 92ft-high War Veterans Memorial Tower rewards you with a forested panorama stretching up to 100 miles across the Taconic, Housatonic and Catskill ranges and over five states. Even if the weather seems drab, driving up to the summit may well lift you above the gray blanket, and the view with a layer of cloud floating between tree line and sky is simply magical.

Mt Greylock State Reservation has some 45 miles of hiking trails, including a portion of the Appalachian Trail. Frequent trail pull-offs on the road up – including some that lead to waterfalls – make it easy to get at least a little hiking in before reaching the summit.

The drive:  Return to US 7 and continue north through the quintessential college town of Williamstown. Cross the Vermont border and continue north through the historic village of Bennington. Just north of Bennington, turn left on Rte 7A and continue north to Manchester.

6. Manchester, Vermont

Stylish Manchester is known for its charming architecture. For fall-foliage views, head south of the center to 3828ft-high  Mt Equinox , the highest mountain accessible by car in the Taconic Range. Wind up the 5.2 miles – with gasp-inducing scenery at every hairpin turn – seemingly to the top of the world, where the 360-degree panorama unfolds, offering views of the Adirondacks , the lush Battenkill Valley and even Montréal ’s Mt Royal . 

If early snow makes Mt Equinox inaccessible, visit 412-acre Hildene , a Georgian Revival mansion once home to the Lincoln family. It’s filled with presidential memorabilia and sits nestled at the edge of the Green Mountains, with access to eight miles of wooded walking trails.

The drive:  Take US 7 north to Burlington. Three miles past Middlebury in New Haven, stop off at Lincoln Peak Vineyard for wine tasting or a picnic lunch on the wraparound porch.

7. Lake Champlain, Vermont

With a surface area of 490 sq miles and straddling  New York , Vermont and  Québec , Lake Champlain is the largest freshwater lake in the US after the  Great Lakes . On its northeastern side, Burlington is a gorgeous base from which enjoy the lake. Explore the lively city by foot, then scoot down to the wooden waterfront promenade, take a swing on the four-person rocking benches and consider a bike ride along the 7.5-mile lakeside path.

For the best off-shore foliage views, we love the  Friend Ship sailboat at  Whistling Man Schooner Company , a 43ft-sloop that accommodates a mere 13 passengers. Next door, ECHO Lake Aquarium & Science Center explores the history and ecosystem of the lake, including a famous snapshot of Champ, Lake Champlain’s mythical sea creature.

The drive:  Take I-89 southeast to Montpelier, passing  Camels Hump State Park and  CC Putnam State Forest . At Montpelier, pick up US 2 heading east to St Johnsbury, where you can hop on I-91 south to I-93 south. Just after Littleton, take US 302 east to Bretton Woods.

8. Bretton Woods, New Hampshire

Unbuckle your seat belts and step away from the car. You’re not just peeping at leaves today: you’ll be swooping past them on zip lines that drop 1000ft at 30mph. The four-season Bretton Woods Canopy Tour includes a hike through the woods, a stroll over sky bridges and a swoosh down 10 cables to tree platforms.

If this leaves you craving even higher views, cross US 302 and drive six miles on Base Rd to the coal-burning, steam-powered Mount Washington Cog Railway  at the western base of Mt Washington , the highest peak in New England. This historic railway has been hauling sightseers to the mountain’s 6288ft (1916m) summit since 1869.

The drive:  Continue driving east on US 302, a route that parallels the Saco River and the Conway Scenic Railroad, traversing Crawford Notch State Park . At the junction of NH 16 and US 302, continue east on US 302 into North Conway.

9. North Conway, New Hampshire

Many of the best restaurants, pubs and inns in North Conway come with expansive views of the nearby mountains, making it an ideal place to wrap up a fall-foliage road trip. If you’re traveling with kids or skipped the cog railway ride up Mt Washington, consider an excursion on the antique Valley Train with the Conway Scenic Railroad , a short but sweet round-trip ride through the Mt Washington Valley from North Conway to Conway, 11 miles south. The Moat Mountains and the Saco River will be your scenic backdrop. First-class seats are usually in a restored Pullman observation car.

This article was first published Sep 3, 2019 and updated Oct 2, 2023.

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Home » Blog » The ULTIMATE New England Fall Road Trip Itinerary

The ULTIMATE New England Fall Road Trip Itinerary

The Northeast USA is arguably one of the most beautiful places in the entire world during fall. For that reason you NEED to add a New England fall road trip to your bucket list!

Prior to this trip, exploring the northeast had been on my travel radar for the longest time. I am stoked to say that New England definitely lived up to the hype and I am excited to share this New England fall road trip itinerary with you all! (3 day, 5 day and 7 day itineraries)

Read on to find out all the must-see places for fall foliage, where to stay, what to pack, the top hikes to take, photography inspiration, and more! I even provide you with a handy map to use for planning and navigation. In my opinion this is the BEST New England fall road trip and I hope you get the chance to take it!

Disclaimer : This blog post may feature some affiliate links, which means I get a small commission if you make a purchase (at no extra cost to you). It’s one of the ways I can keep producing free guides and resources for my readers. Learn more about my affiliate policy  here . Thank you for the support!

New England Fall Road Trip Itinerary

Before we jump into it, I do want to add a disclaimer that this road trip was my own experience during the 2018 fall season . Every year is different, some more magical, and others less so.

I will do my best to help you plan the perfect New England fall road trip itinerary, but you will need to go in with an open mind! Honestly, some of the best trips I have ever taken have been when things haven’t gone to plan. Sometimes all the planning in the world cannot change the weather!

Okay, let’s jump into how to plan a fall New England road trip !

How to plan a New England fall road trip

There are generally two ways to approach planning for a New England fall road trip. The first is to meticulously plan everything in the attempt to not waste a moment, and the second (the option we went with) is to pretty much not plan at all. Sounds weird right? Why would you not plan and wouldn’t that potentially waste you time and money? Well, at this time of the year, it kind of works in the opposite way.

The reason for this is that fall colors gradually change from green, to yellow (or orange, red, purple) until they fall off. Not all trees in an area change at the exact same time. There’s a point in the fall transition where most trees are changed to their beautiful shades of yellow, orange or red prior to falling off and with minimal green trees. This is considered “peak fall foliage” or “peak fall color”.

Peak color doesn’t happen at the exact same time every year (usually varying a week or so either way). It can vary due to a variety of factors but this is mostly due to weather. By not booking hotels or camping prior to your Northeast fall road trip, this allows you to be flexible. You can go to the areas that are at “peak color” rather than spend time in a spot that isn’t yet fully changed or worse, the leaves have fallen.

When to start planning your New England fall road trip itinerary

Advantages and disadvantages come with this method of not planning. The major advantage of not booking all your accommodation in advance is flexibility . You won’t miss the colors because they happened to be a week late or earlier than expected. You can drive to wherever the colors happen to be best in that moment.

This comes with a downside though… accommodation prices and availability. Fall is extremely busy in this part of the country . Like you, many others choose to take East Coast fall road trips in the hope of seeing the incredible beauty that comes with the changing of seasons. This means hotels and vacation rentals can book out well in advance, leaving the remaining last-minute bookings quite expensive.

We ended up opting to mostly find accommodation as we went along, including some last-minute vacation rentals and hotels /motels. We tried to stay at a budget of around $80-150 USD per night, which did narrow down our search a little but overall the places were more than adequate, use Expedia to get price comparisons across multiple booking sites and save you time searching for a place to stay. A couple of times we did have to drive to places slightly further out of town to find a more affordable price but this was an okay compromise to have the extra flexibility.

If you need to rent a car, check out Kayak for price comparisons from rental agents. Or you could use this road trip to test out van life! Rent an RV or camper from Outdoorsy , and you won’t have to worry much about accommodations.

Another option is to bring camping gear .

Keep in mind though, at this time of the year some of the campgrounds are beginning to close. Some places we traveled through didn’t seem to have many tent camping options. In saying that, there was the possibility of sleeping in your car. I have a guide all about sleeping in your car on road trips – check it out!

If you are thinking of camping, you can check sites in the area on The Dyrt where you can see which are open and the facilities available as well as reviews from previous campers. Click here , or use my code reneeroaming for a free 30 day trial .

With all that being said, how you want to plan your Northeast fall road trip is up to you. Do you want to take the chance of potentially missing the peak colors and pre-book more affordable/convenient accommodation? Or do you want to pay slightly more for accommodation and make sure you are seeing the best of the colors? It’s up to you. Either way, we found this be the most accurate and up-to-date map of where the colors are peaking .

Mid-October is often the best time to take a New England road trip for leaf peepers, but it’s helpful if you can be flexible with your date. For reference, we took our fall New England road trip on October 8 – 12, 2018 . But don’t take those dates as a sure thing because peak color can change year to year! Just remember to pack your camera to capture those autumnal colors. You can see the equipment I use further down in the post.

Best New England fall road trip itinerary

Below I’m sharing a suggested itinerary for your New England fall road trip, based on our own adventure. First off, here is a map with all the best spots linked and pins for each day of the itinerary, see below.

Now let’s talk through the day-to-day itinerary…

Day 1 – Dixville Notch State Park

Fly into Boston , Massachusetts and pick up a rental car . From here, drive 4 hours north to Dixville Notch to begin your New England fall road trip. Dixville Notch is a very small area, but for what it lacks in size it makes up for in beauty!

The main road that travels over Dixville Notch initially winds its way past some cute farmland surrounded by rolling hills. The drive then passes stunning Lake Gloriette , up over Dixville Notch and down the other side of the pass-through incredible fall foliage to a couple of serene picnic areas and walks.

Plan to do the stunning Table Rock trail which is a short one at only 1.5 miles round-trip, but a relatively steep 700 feet climb. This gives you epic 360-degree views over Dixville Notch from above, and the photos are beautiful! If you have timed it right, you might even be able to enjoy sunset from up there.

Unfortunately when we were there, the clouds were low and covering the views.

Instead, we parked at what is labeled Whittemore Family Cemetery on GoogleMaps and hiked a short trail that leaves from the parking lot. This is a great alternative if the weather is not cooperating.

This trail made its way through a vibrant forest that leads to a cute little bridge and stream. The hike would only take 10-15 minutes round-trip without stopping. It was a great way to stretch the legs and take a moment to snap some photos of our first glimpse of fall colors.

After finishing your hike at Table Rock, or the alternative trail, head back to nearby Colebrook for dinner and a good night’s rest in your hotel . You can also book into this great cottage on a farm or Tentrr’s Signature Site for luxury glamping.

Day 2 – Stowe

Wake up early, grab some breakfast at Mostly Muffins in Colebrook (so yummy!) and then drive west towards Stowe , Vermont. On the way, you will pass loads of beautiful fall foliage and small rural towns including the memorable Island Pond. The Great Vermont Corn Maze is also a fun stop if you’re into that sort of thing.

After a beautiful drive to Stowe, you can spend the rest of the day exploring its charm, cute gift stores, and scenic walks. We had lunch at the Green Goddess Cafe and it was amazing! We then took a quick walk along the bike path which leaves from behind the Stowe Community Church and runs along the river. You can also take a brewery tour in Stowe to sample locally made beer, spirits and ciders.

From this vantage, there are some great views of the church worth photographing. Finish the night off with a delicious pizza at Piecasso in town – we definitely recommend this restaurant! Stay the night in Stowe at The Green Mountain Inn or in The Loft at Hobble Inn .

Day 3 – Smugglers Notch & White Mountains

Day 3 of your Northwest fall road trip will be a busy one! Wake up early and head to Smugglers Notch . This area has a road that goes up and through a small gap between two mountains (referred to as a “notch”). It is quite similar to Dixville Notch, but in my opinion, Smugglers is even more spectacular.

This was one of the spots we were most looking forward to on our New England fall road trip, and it didn’t disappoint! The mountains on either side are HUGE, and there are so many beautiful twists and turns in the road to photograph and check out.

Definitely drive this to the other side and back before moving on to your next location. Another option is taking the Gondola SkyRide at the Stowe Mountain Resort, for beautiful aerial mountain views.

From Smuggler’s Notch, drive south to Pomfret, Vermont .

Taking Cloudland Road south from Pomfret to Woodstock will take you along cute dirt roads lined with fall colors, rolling hills, and quaint farms. A necessary stop along this route is the farm located opposite “Elm Grove Farm” on GoogleMaps, often referred to as “Sleepy Hollow Farm” . It’s a great little photography stop that captures one of the most photogenic farm properties you will ever see.

Sugarbush Farm is another local property you can visit, though we didn’t go there ourselves. I hear their maple syrup is delicious!

Now, time to head back to New Hampshire! Your scenic drive today will take you through Franconia Notch State Park. At the base of the White Mountains, the town of  Lincoln is a good place to end day 3 of your New England fall road trip. Stay at Woodwards White Mountain Resort or the Loon Mountain Apartment .

Day 4 – White Mountains

Your New England fall road trip would not be complete without a drive along the famous Kancamagus Highway . Leaving early on day 4 from Lincoln, there are a lot of epic road-side views on this stretch of road. A number of pull-outs also allow for some great photo opportunities. Continue east until you hit the Rocky Gorge Parking Lot. Here you can take a walk along the beautiful Swift River and get views of the beautiful Falls Pond . North Conway is a cute town on the east end of the Kancamagus Highway, and a great spot for lunch or a stroll around town.

From Rocky Gorge, we backtracked a short distance to drive up  Bear Notch Road . Bear Notch provides a scenic drive along a mountainside and more roadside pullouts for some gorgeous photo opportunities.

At the end of Bear Notch Road, drive north to Crawford Notch State Park . Here, you can explore the backroads and snap photos of all the beautiful fall colors. A side-trip option in this area is a hike up the Mount Willard trail . It’s a relatively steep, but short 3.2-mile round-trip hike to a clifftop overlooking Crawford Notch. The views from there are unreal! Again, unfortunately, the weather wasn’t cooperating so we had to skip this one.

Next, continue north where you have the option of taking a short detour to the Mt Washington Cog Railway . Here, you can catch an old-school train up to the summit of Mount Washington, the tallest mountain in the northeastern US at 6,289 feet. Due to the bad weather, we kept driving, but if you are a fan of trains then this should not be missed!

To end your day, depending on availability you can stay in the nearby towns of Carroll, Franconia, Littleton, or Bethlehem.

We stayed in Franconia ourselves and chose to drive to Bethlehem to have dinner at the Cold Mountain Cafe . It if works out with timing, we highly recommend it as a delicious way to end a busy day.

There are great hotels to chose from, the Hampton Inn in Littleton and Stonybrook Motel & Lodge in Franconia are lovely options or you can opt for vacation rentals. On the Mountain Suite in Carroll, Rustic Log Cabin in Sugar Hill and Kilburn Place in Littleton are worth checking into.

Day 5 – White Mountains

Day 5 is the last day of your New England fall road trip, and what better way to start than with a sunrise hike up to Artist’s Bluff . This is a short 1.4-mile walk up to a stunning hilltop that overlooks Echo Lake , and the fall foliage here is insane! Unfortunately, it was raining when we drove past here (a common theme on our trip!) so we opted to skip the hike as the clouds were hiding most of the views.

We continued on to Flume Gorge which is a relatively easy 2-mile loop hike and one of our favorite stops of the trip. Multiple waterfalls, streams, and covered bridges keep the eyes entertained for the whole 2 miles. Do note that there is a $18 per person entry fee (I definitely recommend making advance reservations) but we felt it was very much worth it. In fact, we spent a couple of hours exploring this area and even in the rain it was absolutely gorgeous!

By now your Northeast fall road trip is coming to an end. It’s probably time to head back towards Boston to catch your flight… or onward to your next destination (see more below!)

7 day East Coast fall road trip

If you really want to take an incredible Northeast fall road trip and have some extra days ( 1 week total ), here is what I would recommend. Add a couple of days in between Stowe/Smuggler’s Notch and the White Mountains. It would be fun to spend a day in Burlington and walk along Lake Champlain, or check out Waterbury, Vermont. With these extra days, you can drive further into Upstate New York and the Adirondack Mountains , where the colors were absolutely incredible. There are also abundant hiking opportunities, and the beautiful town of Lake Placid to explore. Lake Placid has some amazing accommodation options and beautiful views so it is definitely worth spending a night there. Try the Crowne Plaza or this Rustic Room or search cabins in the area for larger groups.

As an alternative to the Adirondacks, you could scoot over to Maine and visit Bar Harbor and Acadia National Park . Acadia has some really unique scenery, boasting both coastal views and mountain tops! Bar Harbor has plenty of great vacation rentals available.

Check out my blog, How To Prepare for Hiking Trips , ahead of time to prepare!

As I know many of you will ask, we opted to take a sunset hike in the Adirondacks (see photo above), however I have been asked by locals to please not share the exact location. There are some concerns about the potential damage of increased trail traffic and it was pointed out to us that parking spots are also very limited.

I urge you to be responsible and always abide by Leave No Trace Principles when exploring the outdoors. You can read my blog, Hiking Trail Etiquette Rules You Should Know , to learn more and click here to read my in-depth guide on How To Follow Leave No Trace Principles.

3 day New England Road Trip

You could do this New England fall road trip in 3 days with some adventurous spirit! It would be kind of rushed, and you wouldn’t always be able to be in the best spots for sunrise or sunset. That being said, if it’s all you have, go for it! It’s definitely doable and would also be a blast. I hope you don’t mind missing out on some sleep though 😉

Some options to put together a shorter Northeast fall road trip itinerary would be to cut out the Pomfret / Sleepy Hollow Farm section, as that does add some driving hours. Another way to cut downtime would be to combine your visit to Stowe and Smuggler’s Notch into one day.

New England fall road trip packing guide

There are some essential items you should pack for your Northeast fall road trip to make it as enjoyable as possible! I hadn’t explored much of New England or Upstate New York before this trip and found the weather to be a little up and down. In fact, one minute it was sunny and the next freezing and rainy! You’ll definitely want to pack some additional layers for your leaf peeping adventures.

This packing guide is also tailored towards people who enjoy hiking. If you don’t plan to hit the trails, simply leave off the hiking-specific items when using the guide. For those choosing to camp, I have an entire guide and packing list for car camping essentials , so make sure to check that out!

Insulated jacket

Mid-layer :.

Perfect for chilly mornings and evenings. Opt for something lightweight like a fleece or pullover. Recommended mid-layer .

Insulated jacket :

It’s likely to get colder than you are expecting, especially if you plan to be out during sunrise and sunset hours. In fact, it even snowed in New Hampshire towards the end of our trip! So I would highly recommend packing a puffy jacket or a parka that has insulation. Recommended insulated jacket .

Rain jacket :

Do not attempt to take a Northeast fall road trip without a rain jacket/coat ! It rained at least once every day we were on the East Coast. Although it didn’t ruin our trip, it could have if we didn’t have adequate rain protection. Recommended rain jacket , recommended windbreaker .

Casual clothes :

Pack some casual and/or nicer outfits if you plan to eat out at restaurants. This is of course optional though! Check out my Favorites page on Backcountry for some recommendations.

Hiking shoes:

I was VERY happy that I packed waterproof boots for our East Coast fall adventure! We experienced wet, muddy, and cold conditions and waterproof boots made a huge difference. I suggest choosing a pair that can be worn both casually and also when hiking. If you prefer a more solid, supportive hiking boot the Columbia Newton Ridge Plus Waterproof Hiking Boots are a great choice. We also have a guide on all the best hiking shoes , so don’t forget to check that out when shopping for new hiking boots!

Merino wool socks :

Wool socks are the best for preventing blisters and also letting your feet breathe. Recommended hiking socks .

Hiking pants & Leggings:

Don’t stress too much about bottom layers, just make sure they are comfortable and practical for road tripping. I personally like wearing leggings, jeggings, or comfy jeans on road trips, as then I can transition from car, to around town, to hiking, and more. Choose whatever feels comfortable and practical for you! Recommended hiking pants ; hiking shorts ; hiking skort , hiking dress , hiking leggings .

Beanie & Gloves:

As I mentioned above, it even snowed during our New England fall road trip! I would highly suggest packing a beanie and some warm gloves .

Day pack/hiking backpack :

Choose something with hip and chest straps for optimal comfort and practicality. Recommended backpack . When taking short walks or exploring roadside stops I often prefer to opt for a small hip pack instead of a backpack. Just something to fit my phone, lip balm , sunglasses , and any other essentials.

Navigation :

When driving, have Google Maps or Maps.Me handy. We often lost phone service when driving in the mountains of New England and down back roads. For hiking, carry a physical map and a compass , and download offline maps onto your phone. I use Gaia GPS – click here to get 20% off a Premium membership!

Camera + batteries :

Optional but trust me, you will want a camera to capture the incredible fall foliage! Check out the camera gear I use to capture my travel photos and the camera bag I pack it all in!

Every road trip requires snacks! We found it challenging to find food between towns and also after hours. Bring whatever your favorite snacks like nuts, seeds, granola bars, dried fruit, etc. My go-to snacks . If you enjoy drinking coffee then it’s best to bring along a reusable mug or tumbler. Recommended mug ; insulated tumbler . Having your own travel utensils / cutlery is a great way to cut down on single-use plastics when ordering take-out food.

Road trip playlist + Podcasts:

Don’t forget to download some good tunes and podcasts for your road trip. For music, check out my playlists on Spotify . For podcasts, we have an entire guide on the best road trip podcasts !

Want more packing & gear tips?  Check out our guides on what to wear hiking , car camping gear essentials , how to plan a national parks trip , and the best hiking shoes .

I hope that helps you plan an incredible New England fall road trip! With a little flexibility you’re guaranteed to have an epic road trip, even if the weather doesn’t cooperate the whole time. Have an amazing time and feel free to leave a comment and let me know how you got on 😊

PIN for later planning!

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26 comments

Greetings!What are your suggestions for including Salem MA in a 5 day trip? Thank you so much!

• Pingback: New England Fall Road Trip Itinerary - 4 days in New Hampshire & Vermont - Laura Peruchi | NYC

HELLO! Thank you for posting the perfect Fall road trip. I would love to take your advice and incorporate and extra two days to go up into the Adirondacks. Can you please suggest the best place to go and things to do with that two days? I need to book ASAP because we are going the last week of this September. If you could please get back to me quickly, it would be most appreciated. We are from Florida and know nothing of the area, so any advice would be very helpful. Thank you so much. Sincerely, Chris in Florida

• Pingback: 60 Fabulous Fall Aesthetic Photos » Lady Decluttered

Your blog is packed full of helpful information and absolutely beautiful photos!

I was curious if you could recommend an itinerary that would also include Niagara Falls?

I love your photos! Do you offer tours? Thanks!

Hi Renee, Love this post! My fiancee and I are planning our honeymoon to the Adirondacks this fall, so I loved your suggestions and your photographs are beautiful! I was wondering if you knew where you got the grey hoodie you’re wearing in several of your pictures? It’s so cute and looks prefect for fall day hikes.

Hi! Thanks for the wonderful info! We’re just starting to plan a trip for next year. Question, is there nothing to see on the four hour drive from Boston to Dixville Notch? Again, we’re just starting on this, but it appears you’re going up the same way you’re coming back? Thank you so much for the help and this awesome site! 🙂

Gorgeous photos! I’ve spent time in New England in the fall its incredibly idyllic. (Lived in Maine and Massachusetts for 3 years) The White Mountains is truly one of God’s masterpieces. Excellent post!

Hey there!!! As far as the smugglers notch and Stowe area… is it redundant to do the gondola ride as well as take the drive up smugglers notch? Should we pick one or the other? Thanks!

• Pingback: New England Fall Road Trip: The ULTIMATE Leaf Peeping Itinerary - Renee Roaming - Fitness Sport und Gesundheit

Thank you for the Google Maps — so helpful!

Planning a trip for this October, but we have only 3 days! Trying to decide how to see the most of everything! lol any recommendations for “must sees” for only 3 days!?

I can’t wait to travel to the east coast this fall! (I live in California, and we don’t get much of a fall here). Thanks for sharing your itinerary, I’m planning on a road trip and didn’t know where to start! I was wondering where the second picture was taken? (Of you and the water in the background) Thanks!

Did you find out where that 2nd photo was taken? I also would like to go there this October.

I would like to know the shooting spot of the second photo (Stowe?)

This blog post is just amazing and the pictures so beautiful ! Thank you for sharing your experience. I love travelling and was looking for new ideas, this is definitely one 🙂

Wow, these fall colors looks awesome! Thank’s for this helpful post, Renee!

Thank you for reading Laura!

Thanks for sharing your stunning pictures! I totally agree with what you said about not planning in order to find the best colors. The fall we spent living in Upstate NY and hiking all over the NE contained many of my favorite days of my life so far, there truly isn’t a bad hike when it’s that colorful! It makes up for the 6 months of winter that follows. 🙂

What a magical time that must have been!

Thankyou for all this indepth info Renee. Should be super helpful when I plan my own fall trip. And of course stunning photos that I really enjoyed.

Thank you!!

Wow, the nature there looks amazing. And your Photos are loveley. Thank you both for this blogpost. Maybe, we can travel there one day. My wife and I live in the North of Germany. Last weekend we took our own Fall Roadtrip in the Harz National Park. The first blogpost of this trip is now online. It’s about the lovely oldtown in Quedlinburg 😉 best wishes Christian

Thanks Christian! That sounds like an amazing road trip, I’ll add it to my bucket list 😉

i’d love to see Christian’s blogpost about Quedlinburg (a UNESCO World Heritage Site). I was there last year and it was wonderful. My grandparents live in the Harz Mountains, Please share a link, Christian.

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New England Fall Road Trip Itinerary: 10 Stunning Stops

by Mark and Kristen Morgan

Published: August 23, 2021

There are many places in the world you can see leaves turn in Autumn, but they pale in comparison to one famed and celebrated region in the US northeast where science, nature and climate combine to put on an extraordinary light show each year. We are of course talking about fabled New England and we’re going to show you 10 places you can’t miss when planning your New England fall foliage road trip, with 5 day itinerary, 7 day itinerary and 10 day itinerary examples included to help you nail down the best possible route for your trip.

We will use our first hand experiences from road tripping New England in fall to bring you tips, advice and unmissable stops to take on your visit. This is one of those true bucket list USA road trip experiences in which it pays to be organized, plan effectively and make the most of every day.

So, let’s get stuck into those 10 unmissable stops and planning your perfect New England fall foliage road trip itinerary!

The Science Behind Fall Colors

What do we know about the changing of colors to give ourselves the best chance of being in the right place at the right time?

Well, we know that fall colors peak furthest north and work southward through the latitudes. So for example, the Blue Ridge Parkway in Virginia and North Carolina is gorgeous in fall, but the colors won’t change there until much later in the season.

Also, we know elevation plays an important role in when peak colors will be on display. Colors will change first in mountainous regions of Maine, New Hampshire and Vermont before they do at lower elevations.

But the most important aspects are weather conditions leading into Autumn, and amount of daylight. It all starts way back in Spring! A late Spring or intense Summer drought can potentially delay peak fall colors by a week or two.

Conditions Affecting Predictions For Peak Fall Colors

In addition to elevation, latitude and weather conditions before fall, there are more specific conditions that can affect peak fall once we actually reach Autumn:

• Soil moisture levels
• Amount of sunlight during the day
• Length of night
• Day and night temperature (important)

So what would constitute as perfect conditions for the best chance at ‘peak’ fall colors being their most radiant and predictable?

• Wet and warm Spring conditions
• Summer without drought or unusually high / low temperatures
• Warm Autumn days and cool but not freezing nights

And what causes the colors to change once conditions are right?

Sunlight pumps leaves full of chlorophyll during Spring and Summer. Once daylight wanes in Autumn, so does the amount of chlorophyll.

That leaves room for other pigments in the leaves, such as anthocyanin and carotenoids to shine.

Why Focus On VT, NH, ME and Even NY

The region of New England technically contains 6 states; Connecticut, Rhode Island, Massachusetts, Maine, New Hampshire and Vermont. In fall, this entire region transforms into an adventure playground for leaf-peeping lovers and passionate photographers.

However, there are three New England states among the six that we feel just have to be prioritized for the very best scenery and most radiant colors; New Hampshire, Maine and in particular Vermont.

But we’re also going to throw a curve ball by including a region not technically part of New England (gasp!) … New York’s Adirondack Mountains are a stone’s throw from the border with Vermont and the colors are just as special.

We want you to see the best places in New England when you take your fall road trip, but we would prefer you to see the best colors. That means skipping the likes of Boston, Portland and Providence on this particular visit to the northeast.

They’re all awesome places and we visited them all on our New England road trip in fall. But they don’t have the colors of rural Vermont and New Hampshire, plus we had days to spare.

Here’s why you should focus on the northern parts of New England for a fall foliage road trip:

Vermont’s rolling hills are overflowing with charming rural towns, barns and covered bridges. But the state is 80% covered in forest and that can only mean one thing; spectacular fall foliage everywhere you look.

Further Reading: The best places to visit in Vermont

New Hampshire

New Hampshire mixes excellent hiking options in stunning mountainous areas with staggeringly beautiful fall foliage colors.

It also has one of the best mini road trip routes in New England during fall – the Kancamagus Highway.

Maine is huge. It is much bigger than the other New England states and that means it’s hard to fit most of the northern parts in to your road trip. Unless you have more than 2 weeks of course.

However, Acadia National Park is one of the very best places you can visit in all of New England in fall so if you have the spare time, it’s hard to skip.

New York’s Adirondack Mountains, including Winter olympic town Lake Placid and its surroundings are beautiful in Autumn. The popular mountainous region is incredibly popular thanks to a host of activities and of course glorious foliage colors.

When Should You Plan Your New England Road Trip For Peak Fall Colors?

It is impossible to plan the perfect ‘peak’ fall road trip itinerary in New England. You would need to be in many places at the same time for that to be possible. We’re not quite there, yet!

Historically, the last 2 weeks of September and the first 2 weeks of October are when the colors change. So that would put October 1st in the middle of that and therefore a ‘peak’ fall foliage target.

Science tells us that colors change in the North and at elevation first, eventually working South and to lower levels.

We’ll get into example itineraries below, but here are some rough dates to use for each itinerary time frame working North to South:

• 5 Day New England Fall Road Trip – We would suggest aiming for September 29 through October 3.
• 7 Day New England Fall Road Trip – Add a day either side, so September 28 through October 4.
• 10 Day New England Fall Road Trip – Add a day before and two after, so September 27 through October 6.
• 14 Day New England Fall Road Trip – Add a day before and three after, so September 26 through October 9.

Should You Book Your Trip In Advance?

Here are two scenarios:

• You don’t book in advance and keep an eye on live fall foliage updates to guarantee hitting peak fall. This also means you have flexibility on bad weather days. However, there are very limited hotels available and those that do have rooms will be more expensive.
• You plan and book your whole trip in advance, getting good value in hotels and can relax. But there’s a chance you won’t time it just right and you will have to deal with whatever weather comes your way.

We can’t offer a ‘better’ solution here because both have pros and cons.

Our trip was mainly booked in advance which meant we spent less but we had to put up with a lot of disappointing rain days, as you will see in the photos below!

Need a hand planning your New England fall road trip? Our popular 40+ page New England Fall Road Trip Guidebook includes the 10 best places to visit, 8 example itineraries ranging from 5-14 days and an extensive interactive map to help you plan a successful leaf-peeping vacation.

Top Tips For Planning Your New England Fall Road Trip Itinerary

Finally, before we jump into the 10 unmissable stops and the New England fall road trip itineraries, let’s have a quick look at some important tips to consider when planning your vacation:

• New England is insanely popular in fall.
• Booking accommodation in advance will save you a lot of money.
• Carefully plan where you want to spend each night based around hikes and photography.
• Start in the North and work South through New England.
• Expect frequent rain and clouds in fall and accept that there’s nothing you can do about it!
• Always carry loads of water and snacks in the car.
• Try to find elevated vantage points as often as possible.
• Some of the best and most unique fall photos are along rural country roads.
• You need multiple spare batteries for your camera!
• You can use a drone in many parts of New England for aerial photography.
• Don’t worry if you miss ‘peak’ colors.

Our popular road trip resources:

• Road trip packing list essentials
• How to plan the perfect road trip

10 Places You Can’t Miss On The Best New England Fall Road Trip

Let’s take a closer look at the 10 stops we think are unmissable on a first New England trip to see the fall colors.

1. Lake Placid, New York

Lake Placid of 1980 Winter Olympics ‘Miracle on Ice’ fame is located at the heart of New York’s revered Adirondack Mountains. It is the perfect base for adventure activities throughout all four seasons, from hiking in Summer to skiing in Winter.

The charming town of Lake Placid is an incredibly popular centralized location for leaf peeping in the Adirondacks. As a result, hotels here are in high demand and not cheap from the end of September until mid October. We know from experience when our bank balance took a mighty hit!

Walk around Mirror Lake in town for the easiest way to soak up gorgeous fall colors. If you have time and enjoy challenging hikes, you can’t miss Mount Marcy. It isn’t the prettiest trail but it is the tallest peak in New York.

Things To Do In Lake Placid, NY

• Take a relaxing walk around serene Mirror Lake.
• Visit the Olympic ski jumping complex.
• Photograph John Brown barn.
• Drive to the summit of Whiteface Mountain.
• Take the Cloud Splitter cable car to Little Whiteface.
• Walk through picturesque High Falls Gorge.
• Hike Mount Marcy, the tallest peak in New York.

Where To See Fall Foliage In Lake Placid, NY

• Mirror Lake in town is gorgeous, walk through residential areas surrounded by colorful trees.
• John Brown barn is a hidden gem for fall colors.
• The top of the ski jump provides sweeping views over the Adirondacks.
• Mount Marcy summit is the highest point in the entire region, providing the best views over rolling hills.
• Whiteface Mountain and Little Whiteface offer more stunning views of fall foliage.

Read our Lake Placid guides for more information:

• 10 best things to do in Lake Placid NY
• Mount Marcy complete hiking walkthrough
• 8 best hotels in Lake Placid NY

2. Burlington, Vermont

Burlington in Vermont might not be the first place you think of for a New England fall foliage road trip destination. However, it is one of the easiest places outside of Boston to fly into the region if you are visiting from further afield.

The small town also happens to be filled with beautiful and radiant foliage colors at every turn. From lakeside bike paths to park towers with stunning views, Burlington is the perfect stop off between Lake Placid and the more famous foliage destination of Stowe.

Hotels in downtown Burlington can be limited and expensive in Autumn, so if you are visiting New England on a budget, try looking for hotels in surrounding villages and towns.

Things To Do In Burlington, VT

• Eat, drink and soak up the atmosphere along Church Street.
• Walk through Waterfront Park alongside Lake Champlain.
• Cycle the Burlington bike path to Grand Isle.
• Explore Ethan Allen Homestead and Museum.
• Stand on top of Ethan Allen Tower for amazing views.
• Taste chocolate at Lake Champlain Chocolates flagship store.

Where To See Fall Foliage In Burlington, VT

• Anywhere along the Lake Champlain waterfront where there are trees.
• Ethan Allen Park and the top of the tower in particular have the best fall foliage views in Burlington.
• Ethan Allen homestead and museum are surrounded by beautifully colorful trees.

Read more about Burlington:

• 10 best things to do in Burlington VT
• 8 best hotels in Burlington VT

3. Stowe, Vermont

Stowe is one of the unmissable fall foliage classics on any New England road trip. The white church in town is one of the most photographed churches in the US and almost all of those photographs are taken in fall.

The town is quaint and attractive but be sure to spend the majority of your time up in Stowe Mountain Resort. This is where you will find hikes, Mt Mansfeld, waterfalls and Smugglers Notch.

Colors will change first up in the higher elevations. So, if you’re a little early, head up to the resort. On the other hand, if you’re a little late, stick to the lower elevations around Stowe town for the most vibrant colors.

Personally, we love to hike, we like flying our drone and we enjoy photographing waterfalls. Stowe was one of the best stops on our New England fall road trip circuit for allowing us to do all of those things.

Things To Do In Stowe, VT

• Photograph the famous white church in Stowe town.
• Drive or hike to the summit of Mount Mansfield.
• Drive through stunning Smugglers Notch pass.
• Ride a bike along Stowe Rec Path or Lamoille Valley.
• Take the SkyRide Gondola to Mt Mansfield.
• Hike a wide range of awesome trails.
• Visit both Bingham Falls and Moss Glen Falls.

Where To See Fall Foliage In Stowe, VT

• In Stowe town, the iconic white church backed by a hill of fall colors is unmissable on your New England road trip.
• But the best colors are in Stowe Mountain Resort. The drive up from town is gorgeous.
• No matter how you get to the top of Mt Mansfield, you can guarantee spectacular fall foliage views.
• Smugglers Notch is our top recommendation for Stowe. If you have a drone, this is the place to fly.

Read more about Stowe, Vermont:

• 15 best things to do in Stowe VT
• 12 best hotels in Stowe VT

4. Woodstock, Vermont

Woodstock in central Vermont is arguably the most picturesque and charming town you will visit on your New England fall road trip itinerary. It truly is like something out of a fairytale. We had no choice but to include Woodstock in our popular guide to the 50 best places to visit in the USA .

Remarkably pretty farms with golden leaves dancing in sunlight and reddish-brown leaves covering the ground create picture perfect scenes. Sleepy Hollow Farm and Jenne Road Farm are featured on many fall foliage calendars you will see in shops on your visit to New England.

Don’t miss the many stunning historic covered bridges around Woodstock. Middle covered bridge is right in town, Taftsville and Quechee are very close by and Cornish-Windsor is a 30 minute drive. The beautiful bridge in the photo below is a privately owned bridge near South Woodstock on the main road to Jenne Farm.

Woodstock is one of the more expensive places to visit on a road trip through Vermont, but it is worth taking a hit on the extra chunk of budget. Simply driving around the narrow country roads near Woodstock for a few hours would provide enough fall foliage colors to last a week of photography.

Things To Do In Woodstock, VT

• Walk around the charming town and admire diverse architectural styles.
• Photograph two postcard perfect farms – Jenne Road Farm and Sleep Hollow Farm.
• Visit a host of historic and stunning covered bridges.
• Explore Marsh Billings Rockefeller Park and hike to amazing viewpoint overlooking Woodstock.
• Visit nearby Quechee Gorge and village.
• See Jersey dairy cows at Billings Farm and Museum.

Where To See Fall Foliage In Woodstock, VT

• Woodstock is incredibly photogenic during fall throughout the town and immediate surroundings.
• The lookout over Woodstock from Mount Tom hike is iconic fall photography.
• The best two fall photographs in Woodstock are at Jenne Road Farm and Sleepy Hollow Farm. They are two truly unmissable stops on your New England fall road trip itinerary.
• Drive your car around the narrow rural roads near Woodstock for some of the most special colors.

Read more about Woodstock, Vermont:

• 15 best things to do in Woodstock VT
• 7 best hotels in Woodstock VT

5. Manchester, Vermont

Similarly to Stowe, Manchester is a four season resort with skiing in Winter and hikes during Spring or Summer. In fall, the town located in the heart of Green Mountain National Forest transitions into a colorful paradise for leaf-peepers.

Manchester can be split into the old historic district and the newer modern resort town. The newer part is livelier and closer to amenities but the historic district is quieter, prettier and more colorful.

Use Manchester as a base for one night to explore nearby elevated areas for some of the most expansive views of rolling hills on a New England fall road trip.

Equinox Mountain is the tallest peak in the area. You can hike it or drive it to open up far-reaching views over three US states. But our top tip is to simply stick to the narrow country roads again and you will find more unique fall foliage photographs.

Things To Do In Manchester, VT

• Drive the Skyline Auto Toll Road to Mount Equinox summit.
• Explore Hildene, the Lincoln Family Home.
• Walk around quaint Manchester Historic Village District.
• See the American Museum of Fly Fishing Museum exhibits.
• Buy a book in popular Northshire bookstore.
• Visit nearby covered bridges.
• See the Bennington Battle Monument.
• Visit Robert Frost stone house museum.

Where To See Fall Foliage In Manchester, VT

• Manchester is the heart of the Green Mountains, so the entire area surrounding the town is staggeringly attractive.
• Rolling hills for endless miles covered in glowing fall colors can be seen from any elevated vantage point.
• Equinox Mountain summit provides the best panoramic views over three states.
• Another place you jump in the car and find unique fall photography opportunities on rural roads.
• Manchester Historic Village District is leafy and the church is surrounded by golden yellow leaves.

Read more about Manchester, Vermont:

• 15 best things to do in Manchester VT
• 9 best hotels in Manchester VT

6. Franconia Notch State Park, New Hampshire

Franconia Notch is one of New Hampshire’s premier tourist regions for hiking, picturesque mountains, skiing and of course fall foliage. A two lane highway mountain pass dissects the Kinsman and Franconia mountain ranges, with a number of fantastic recreational stops along the way.

Artists Bluff is a very short but steep hike leading to a rocky ledge. Its summit overlooks Echo Lake and is most popular in fall when the colors change. As you can see, we hiked the trail on an incredibly cloudy and grey day, which doesn’t help with highlighting the beauty of this viewpoint. We have included Artists Bluff in our popular guide to the 50 best hikes in the US .

Franconia Notch State Park is where you will find the stunning Flume Gorge hike. A little over 2 miles of waterfalls, narrow gorges and forested paths welcome thousands of visitors each year. For us, the best part of Flume Gorge were the two ultra-photogenic covered bridges; Flume and Sentinel Pine.

Things To Do In Franconia Notch State Park, New Hampshire

• Hike the short but steep trail to Artists Bluff summit for stunning views.
• Walk through impressive and extremely popular Flume Gorge.
• Hike Cannon Mountain or take the Cannon Mountain Aerial Tramway.
• See a whole host of waterfalls or hike one of a dozen other mountain trails.
• Ski Cannon Mountain Resort in Winter.

Where To See Fall Foliage In Franconia Notch State Park, New Hampshire

• The single most well known fall foliage photograph in Franconia Notch NH is from the summit of Artists Bluff.
• However, don’t miss the chance to walk through the incredibly picturesque Flume Gorge in fall.
• Not only are the colors vibrant, but waterfalls are attractive and two special covered bridges are incredibly photogenic.
• Anywhere at elevation, which means every hike up a mountain side or the tramway with sweeping valley views.

Read more in our Franconia Notch guides:

• Artists Bluff Trail Fall Foliage Hike
• Flume Gorge Complete Hiking Walkthrough

7. Kancamagus Highway, New Hampshire

New Hampshire’s supremely scenic Kancamagus Highway is one of the very best parts of New England to road trip in fall foliage season. We would put it firmly in the category of ‘unmissable’.

The road between Lincoln and Conway NH is only 35 miles long, but it 35 miles of pure foliage bliss. You can either drive it in one go and simply soak up the colors roadside. Or you can stop at a multitude of overlooks, hiking trails, waterfalls, lakes and covered bridges.

If there’s one part of your New England road trip itinerary to time it right for peak foliage colors, you would do well to beat the Kancamagus Highway in its prime.

A note for photographers and videographers – You can use your drone in many parts of the Kancamagus Highway. We captured amazing photographs and videos of endless miles over rolling hills covered in radiant color.

Things To Do On Kancamagus Highway, New Hampshire

• Stop at various high elevation overlooks with spectacular views over White Mountain National Forest.
• Walk to Sabbaday Falls, Champney Falls and Lower Falls.
• Hike Lincoln Woods or Mount Chocorua.
• Walk out on Rocky Gorge boulders.
• Photograph Russell-Colbath House and the picture perfect Albany Covered Bridge.
• Explore ponds and lakes to your hearts content.

Where To See Fall Foliage On Kancamagus Highway, New Hampshire

• Views over rolling hills from every overlook are astonishing in fall.
• Once the Kancamagus Highway reaches its highest elevation, you will see an ocean of color in all directions.
• Walk through any forest trail or along any waterfall hike to immerse yourself into those foliage colors.
• Albany covered bridge is one of the most picturesque bridges you will find in New England.
• Rocky Gorge and nearby lake with reflecting fall colors are wonderful.
• Even on both ends of the road in Lincoln (Loon Mountain) and Conway the colors are vibrant.

Read more about the Kancamagus Highway:

• 13 best places to stop along the Kancamagus Highway in fall

8. Mount Washington, New Hampshire

At 6,288 ft tall, Mount Washington is the tallest peak in Northeastern United States. It is renowned for wild and unpredictable weather, including the recording of a world record wind speed over over 230 mph.

As our images indicate, Mount Washington can be very wet and cloudy in Autumn. But if you get slightly more luck on your road trip and time it on a sunny day, you will enjoy some of the most beautiful colors and scenery in the entire region.

Avid hikers can climb to the summit, otherwise you can take a historic cog rail train or drive up an auto toll road to reach the top. Views from almost 2,000 meters high over an ocean of bright colors are incredible.

Things To Do Around Mount Washington, New Hampshire

• Hike a very challenging but rewarding trail to the summit of Mount Washington.
• Consider a night hike, fall colors won’t matter in the dark but it is hugely popular for astro and sunrise photography.
• Alternatively, drive the Mt Washington Auto Road to the summit.
• Or, take the most scenic and historic route to the top – by Cog Railway.
• Conway scenic railroad nearby ventures deep into fall foliage forest.
• Endless miles of hiking, 100 waterfalls and a handful of covered bridges to discover.
• Crawford Notch State Park is close by and features more views, hikes and waterfalls.

Where To See Fall Foliage Around Mount Washington, New Hampshire

• Just gain elevation in the White Mountains and you’ll open up valley views with a sea of foliage colors.
• Mt Washington summit is the iconic NH vantage point for sweeping Autumnal vistas.
• For a unique experience, the Conway Scenic Railroad cuts through some of the best colors in NH.
• Crawford Notch State Park is stunning in fall, with fantastic valley views from hikes.

9. Lake Winnipesaukee, New Hampshire

Heading due South of Mt Washington you will find Lake Winnipesaukee encircled by gorgeous fall foliage colors. Unfortunately for us, the rain was back in full swing but you can still see how vibrant the colors are in this area.

You can drive an 81 mile loop road around the entirety of the lake, or take to the waters aboard M/S Mount Washington cruise boat.

Visit Castle in the Clouds for family entertainment and hiking, Weirs Beach for arcades or Wolfeboro for a more relaxing experience. The most popular trail in the area is Mount Major, which we highly recommend for hikers looking for excellent views over the lake.

Things To Do Around Around Lake Winnipesaukee, New Hampshire

• Take a cruise on the M/S Mount Washington.
• Or rent a boat of your own for the day.
• Ride the Lake Winnipesaukee scenic railroad.
• Try your hand at arcade games in Weirs Beach.
• Hike the popular half day trail to Mount Major summit for fantastic lake views.

Where To See Fall Foliage Around Lake Winnipesaukee, New Hampshire

• Elevation is your fall foliage friend around the lake if you want expansive views.
• Mt Major is the perfect moderate hike to include on your New England fall road trip itinerary.
• But nearby Belknap Mountain is also a popular choice for fall hikers.
• Gunstock Mountain Resort has zip lines and ski lifts for easy elevation gain.
• For easier and more close up Autumnal color vistas, simply hire a boat on the lake and explore.
• Or sit back, relax and soak up the views on Lake Winnipesaukee scenic railroad foliage tour.

10. Acadia National Park, Maine

Acadia finds itself in the list of top 10 most visited and best US National Parks each year. Millions of tourists descend on Bar Harbor annually to enjoy a diverse range of amazing things to do inside the awesome park.

Varied hikes suitable for all ages and abilities, including the famous adrenaline pumping climbs Beehive Trail and Precipice Trail , are a huge draw. But despite being a typical Summer destination in the north of America, Acadia is equally as popular in Autumn and that is purely down to its glowing fall foliage colors.

Sunrises from Cadillac Mountain or Schoodic Point can be extraordinarily beautiful if conditions are right, and sunset at Bass Harbor Head Light is a very highly regarded spectacle. You will need to bring your best hiking gear, spare camera batteries and a lot of energy to the wonderful National Park in Maine.

The only problem you will face with including Acadia on a New England fall foliage road trip is its location. You will have a long drive to and from Acadia from Vermont or New Hampshire. However, if you have the time, it is unquestionably worth the extra effort.

Things To Do In Acadia National Park, Maine

• Hike various amazing trails from easy to hard (to exhilarating!).
• Photograph stunning sunrises, landscapes and Bass Harbor Head Light.
• Drive to Cadillac Mountain summit, the tallest peak on the US east coast.
• Walk or cycle maze-like carriage roads through the park.
• Explore Jordan Pond and swim in Echo Lake.
• Eat and drink in glitzy Bar Harbor, Maine.

Where To See Fall Foliage In Acadia National Park, Maine

• Mountain summits from any hike opens up special views over rolling hills covered in fall colors.
• Carriage roads are the perfect way to explore forested trails which are surrounded by trees.
• Drive the national park loop road for easiest access to fall colors.
• Jordan Pond in particular is encircled by vibrant autumnal hues.
• Cadillac Mountain summit opens up 360 degree views over Maine and the ocean.

Read our Acadia National Park guides to learn more:

• 17 best things to do in Acadia National Park
• 10 hikes you can’t miss in Acadia National Park
• Where to stay in Bar Harbor and Acadia National Park
• 10 key things to know about visiting Acadia in the fall

Planning Your New England Fall Road Trip Itinerary

New England is an enormous region and choosing exactly where to visit can be challenging. Here are a few questions to ask yourself before you begin plotting a route:

• Which places are top of your list? Vermont? New Hampshire? Acadia?
• How many days can you spare on your trip?
• Do you want to book accommodation in advance or take it day by day?
• Are you in New England solely to see and photograph fall colors?
• Or are you focused primarily on hiking with colors as an added bonus?
• Do you want to use small and quaint towns as your main places to stay?
• Or are you more interested in being rural and remote each night?
• What is your budget? Can you afford to splurge on activities?

Once you have an idea about how you see your road trip panning out, use that idea as a guide to make the best decisions based on your travel style.

Next, we will go through a number of potential scenarios for 5 day, 7 day and 10 day road trip examples through New England in fall.

Use the examples as a reference but remember, they are generic and based on how we personally would plan our itineraries with hikes and photography in mind.

5 Day New England Fall Road Trip Itinerary

Only having 5 days isn’t as much of a negative as it might usually be. Yes, you are going to have to be selective and it is going to be none stop action. But one of the major benefits to a road trip in fall is that all of the best scenery is seen when driving.

Also, the smaller states of Vermont and New Hampshire don’t require a huge amount of drive time between their most scenic places for fall foliage. Include Lake Placid in the Adirondacks and you can easily tick off most of the places in our list in 5 days.

Another consideration is with just 5 days you don’t need to worry as much about ‘following’ peak fall colors. They won’t change too much in that time frame when compared to 10 days.

Example 1 – Lake Placid NY to Manchester VT

D1 – Lake Placid : Walk around Mirror Lake, drive up Whiteface Mountain and explore High Falls Gorge. Stay in Lake Placid.

D2 – Burlington and Stowe : Walk down Church Street, cycle Burlington bike path, explore Smugglers Notch and Stowe Mountain Resort, sunset at Stowe church. Stay in Stowe.

D3 – Franconia Notch and Kancamagus Highway : Hike artists bluff trail, walk around Flume Gorge, drive Kancamagus Highway and down to Wolfeboro. Stay in Wolfeboro on Lake Winnipesaukee.

D4 – Lake Winnipesaukee and Woodstock VT : Spend morning exploring the lake or hike Mt Major, then drive to Woodstock in Vermont via Cornish-Windsor covered bridge, Quechee Gorge and Taftsville covered bridge.

D5 – Woodstock and Manchester : Visit the farms near Woodstock, drive through Green Mountains to Manchester and end at the top of Equinox Mountain.

You could start and end in New York City if flying into Newark or JFK works from your origin and budget. Alternatively, Montreal would be a better place to start for Lake Placid, hire a car and drop it off in NYC or Boston after leaving Manchester, VT.

Example 2 – Lake Winnipesaukee NH to Manchester VT

D1 – Lake Winnipesaukee : Explore the lake, hike Mt Major, take a cruise and stay in Wolfeboro.

D2 – Kancamagus Highway and Franconia Notch : Drive Conway to Lincoln across Kancamagus Highway, hike Flume Gorge and Artists Bluff. Sleep in Franconia.

D3 – Stowe and Burlington : Stowe church, hike to waterfalls in Stowe Mountain Resort, drive Smugglers Notch and on to Burlington. Ride the bike path for sunset. Stay in Burlington.

D4 – Lake Placid : Whiteface Mountain, High Falls Gorge, Ski Jump and Mirror Lake. Or hike Mount Marcy instead but that is a full day commitment. Stay in Lake Placid.

D5 – Woodstock and Manchester : Visit the farms, covered bridges and drive through Green Mountain countryside to Manchester, finish with Equinox Mountain again.

This version would allow for a round trip loop from Boston, MA airport or Portland, ME airport.

The key to making the most of this shorter trip is to accept that you will be in the car driving a lot but that is where you will see most of the best scenery.

7 Day / One Week New England Fall Road Trip Itinerary

With a week, you can get more creative, include more places or take things slower. You have more flexibility but still not enough time to add a trip to Acadia, unless you really can’t miss it and don’t mind the driving.

Colors can change a noticeable amount in 7 days, so (if possible!) factor in starting your one week trip just before ‘peak’ begins.

Either of the 5 day examples above would work with 7 days by simply taking more time in certain spots. The alternative is to add in more places to visit. Let’s look at both:

Example 1 – Lake Winnipesaukee NH to Manchester VT

D2 – Kancamagus Highway : Take the awesome road trip slowly, stop at every attraction and stay in Loon Mountain or Lincoln.

D3 – Franconia Notch and Stowe : Hike Flume Gorge and Artists Bluff before driving to Stowe to photograph the church. Hike the waterfall trails and see Smugglers Notch. Stay in Stowe.

D4 – Burlington and Lake Placid : Church Street and Burlington bike path, then drive to Lake Placid, get stuck into the best bits of Lake Placid and spend the night there.

D5 – Lake Placid and Woodstock : Spend the morning in Lake Placid and drive to Woodstock later in the day. Hike to Mount Tom for amazing views over Woodstock. Stay in Woodstock.

D6 – Woodstock : Sunrise at Sleepy Hollow Farm, Jenne Road Farm, visit the nearby covered bridges and relax in town. Drive to Manchester later in the day to stay over.

D7 – Manchester : Hildene, Manchester old town and stunning Green Mountain country roads, finish at Equinox Mountain.

This variation could begin and end at either Boston, MA or Portland, ME as in the itinerary above. It just gives you more downtime and time to fully explore the places you will visit.

Example 2 – Manchester VT to Lake Winnipesaukee NH

D1 – Manchester : Drive from Boston airport to Manchester, spend the day at Hildene, Equinox Mountain and exploring the town. Stay in Manchester.

D2 – Woodstock : See the best of Woodstock and spend the night.

D3 – Stowe : Hit the top highlights in Stowe and stay there for the night.

D4 – Mount Washington : Take the cog train, drive to the summit or even take on the hike. Sleep in North Conway.

D5 – Kancamagus Highway : Spend a full day on The Kanc. Sleep in Loon Mountain or Lincoln.

D6 – Franconia Notch : Hike Flume Gorge and Artists Bluff but drive to Lake Winnipesaukee later to spend the night.

D7 – Lake Winnipesaukee : Spend the last day around the lake, cruising, hiking or relaxing.

This loop direction was reversed to give an idea about how you could make it work in a clockwise route. Again this would be starting and ending in Boston or Portland, with JFK or Newark as alternative options.

Instead of driving out to Lake Placid, you could stick to Vermont and New Hampshire, which is where the very best colors are found.

10 Day New England Fall Road Trip Itinerary

With a full 10 days to spend on your New England fall road trip, you can either max out your itinerary and see all of the best bits or choose to spend more time in fewer places.

Personally, we’re the max out itinerary type and we would definitely include Acadia National Park in our 10 days. It adds in some serious driving time but the journey there is picturesque, rural and most importantly colorful.

Here’s one way you can include each of the places mentioned in this list, including Acadia National Park (this is the way we drove but we spent 14 days doing this route with other non-fall foliage places included in our itinerary):

Example 1 – Lake Placid, NY to Manchester, VT via Acadia National Park, ME

D1 – Lake Placid : Spend the day hiking and surrounded by gorgeous colors. Sleep Lake Placid.

D2 – Burlington : Full day exploring town and cycle the entire bike path to Grand Isle. Stay in or near Burlington.

D3 – Stowe : Smugglers Notch, Mountain Resort, Mt Mansfield and church in town. Stay in Stowe.

D4 – Franconia and Kancamagus Highway : Hike Artists Bluff and Flume Gorge, drive The Kanc and sleep in North Conway.

D5 – Mt Washington and drive to Acadia : Drive to the summit or take the cog train before driving US-2 all the way to Acadia. Sleep in Bar Harbor.

D6 – Acadia : Sunrise Cadillac Mountain, Hike Acadia Mountain and Beech Mountain, sunset at Bass Harbor Head Lighthouse. Stay in Bar Harbor.

D7 – Acadia : Sunrise Schoodic Point, Hike Beehive Trail and Precipice Trail, Walk around Jordan Pond, Great Ocean Path and carriage roads by bike to see the best fall colors. Final night in Bar Harbor.

D8 – Lake Winnipesaukee : Final morning in Acadia, long drive to Wolfeboro and explore Lake Winnipesaukee.

D9 – Woodstock : Photograph Sleepy Hollow and Jenne Road, hike to Mt Tom, see covered bridges.

D10 – Manchester : Hildene, Mount Equinox, nearby Bennington battle monument and covered bridges.

Tips For The 10 Day Itinerary

The only concern with this itinerary is the inclusion of Acadia National Park. It’s a 4 hour drive from Mt Washington to Acadia and 4 hours 20 minutes back from Acadia to Wolfeboro.

However, if you do have more time you can include stops on the way to and from Acadia to break up the longer drives. US-1 and US-2 are picturesque but slow going. If you’re pushed for time, take the less scenic but faster I-95 instead.

Alternatively, if you’re not so bothered by Acadia, plan to spend even more time in each of the other 9 places in this list. That would give you wiggle room in case of bad weather and plenty of time to relax.

Notice how the route starts furthest north and loops around Acadia then comes back further south?

That’s because with 10 days you should try to ‘follow’ the peak colors as they transition southwards over the first two weeks of October.

New England Fall Road Trip Map

Red Markers – Locations of the 10 best places to visit on a New England fall road trip itinerary.

Click or touch the map to activate.

Zoom in and out, move around the map of New England to find locations for the best places to visit in the area.

More From New England

• Best things to do in Burlington Vermont
• Best things to do in Woodstock Vermont
• Driving the Kancamagus Highway in fall
• How to visit Flume Gorge in New Hampshire
• The best things to do in Lake Placid New York
• The best things to do in Stowe Vermont
• Top things to do in Manchester Vermont
• Unmissable things to do in Acadia National Park

We hope this New England fall foliage road trip guide with itinerary ideas helps you plan the perfect leaf-peeping vacation!

Please let us know if you have any questions about New England or need any help planning your visit in the comments below.

Happy Travels,

Mark and Kristen

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Mark and Kristen Morgan are travel, hiking and photography experts. Over the last 6 years traveling full time, they have explored more than 40 countries and 30 US states.

Where Are Those Morgans has been featured in USA Today, Gestalten, Get Your Guide, CityPASS and Condé Nast Traveler along with various other publications. Read more about us .

29 thoughts on “New England Fall Road Trip Itinerary: 10 Stunning Stops”

I really appreciate your compressive guide to New England for travel in the Fall. We have enjoyed most of the areas you mention in years past and loved it. My sister is visiting from Australia at perfect Fall Foliage time so we’re planning to do your 10-day roadtrip this year. I was wondering if you have an App you prefer to use to plan each segment of the roadtrip. I used Roadtrippers earlier this year and found it good, but would welcome your suggestions for a roadtrip App. I plan to download your digital guide as well. Thank you and happy travels.

Hi Sharon, we’re happy to hear you will be visiting New England again and this time with your sister. If you are looking for alternatives to Roadtrippers you could check out Wanderlog which is another useful resource. But to be honest we don’t use any apps for our road trips except for the basic and free Google Maps app. We plot points for attractions, restaurants and hotels as we research before visiting a new place, and we plan ahead so we can really get organized. If you download our digital guide and go to the end, you will find a map we created that will open in your Google Maps app and it already contains the locations for top attractions, foliage photo spots, hikes, restaurants and hotels that we discuss throughout the guide. You can of course see more places but we have preloaded the map with the essential spots to visit around New England in fall. Have a fantastic trip!

@Mark and Kristen Morgan, Thank you so very much for your advice. I downloaded the digital guide to use. So looking forward to this trip and having your guide to get organized makes this a lot less daunting. Keep up the great work and happy traveling.

Hi Sharon, Visiting New England in fall is an amazing trip and you will have a wonderful time! Thanks so much for taking the time to leave a nice comment and downloading our guide. Just let us know if you have any specific questions as we get closer to fall season 🙂

@Mark and Kristen Morgan, I have accommodations booked from Lake Placid to Woodstock. Since we want to add a couple of nights in Boston to walk the Freedom Trail and visit the Boston Tea Party site, would you recommend skipping Manchester, Vermont and going directly to Boston from Woodstock. Or, would we be missing out if we skip Manchester. Appreciate your advice.

Hi Sharon, you will have covered almost all of the best fall spots between Lake Placid and Woodstock. We like Manchester but it isn’t going to ruin your trip if you skip it, especially if you really want to see more of Boston. After 10 days or so you will have had your fill of fall colors anyway, so Boston will be a welcome change of scenery and pace. Have a fantastic time!

I would love a copy of the book as well, to use as we travel Thank you for a wealth of information!

Wow, amazing information, thank you. Have you written it in book form by any chance? I would love to drive with the book on hand for reference.

Hi Helen, you have asked at just the right time. We are currently in the process of creating a digital guidebook filled with key information and itinerary ideas for the New England fall road trip. It will be ready within the next week or so and we will email you once it is live. You will be able to either keep it on your smartphone or print it if you prefer to have a paper copy.

@Mark and Kristen Morgan, I’m using this article to plan our New England fall leaves trip and would also be interested in a copy of your digital guidebook, please. The information you provide is outstanding — thank you! ~ Carol

Thank you, Carol! We’re happy to hear you are planning a New England trip this fall. You can follow this link to see more details about our digital guidebook. If you do purchase the guidebook, remember to open up the map on page 45 when you are in each place to see the best hikes, foliage spots, attractions, restaurants and hotels. And if you have any specific questions, feel free to ask away. Have a fantastic trip!

Hello! What a wonderful site you have given us :). Question…do any of the New England fall road trips include the Berkshires? I would love to include a quick visit to The Mount/Edith Wharton’s home. Thanks, Jo

Thank you, Jo! Yes absolutely, you could easily add The Mount / Edith Wharton’s Home to the end of our 10 day New England fall road trip itinerary because it is just 1 hour 30 minutes drive to the south of Manchester VT (which is the last stop in our guide), before heading back to the Boston / NY airports. It wouldn’t be much of a detour and if you are heading that way you might also want to consider including a short drive along scenic highway 2, also known as The Mohawk Trail. Have a fantastic trip later this year!

Hi There! We are flying into Portland, (Sept 23rd) Maine and flying out of Boston, Mass (October 2nd) We have about one full week for our Fall Foliage road trip. Knowing we arrive Portland and depart Boston, what would you map out for itinerary.

Part II question, I prefer staying at one hotel for a few days and taking day trips as opposed to staying one night in several places.

Would it be wise to stay 3 nights near Acadia Nat’l Park and then 3 nights in New Hampshire (near all of the Franconia State Park and Kancamagus Hwy ?

Hi Erin, yes staying 3 nights in Bar Harbor and then 3 nights somewhere near Franconia Notch sounds like the best idea if you would prefer to stay in one hotel for each part of your trip. You can easily visit the most popular fall foliage areas in VT and NH from Franconia. Depending on how much driving you want to do, you could split your days into Vermont and New Hampshire. So one day you do Stowe, Woodstock and Manchester (the driving in between is just as picturesque as the towns), then another day you do Mt Washington, Kancamagus, Artists Bluff and Flume Gorge (which are all much closer together). Then stop at Lake Winnipesaukee on the way down to Boston. Hopefully the peak colors will be in north / central VT and NH early Oct for your trip – have a great time!

Love your site! we are planning a a Fall Foliage trip for 2023 over our 34th Anniversary. thinking any where from 10 – 14 days from the last week in Sept. to the first week of Oct. We are thinking to end our trip in Boston for a few days. If I followed tour 10 day trip guide would it make sense to fly into Albany, NY and out of Boston. Or are we better off to make Boston a long weekend trip?

Hi Randy, thanks for getting in touch and we’re happy to hear you’re planning a trip to New England next year, congrats on the 34th! Absolutely, flying into Albany and out of Boston makes perfect sense. If you make your trip 14 days total, you can follow the 10 day itinerary in our guide and then spend 2 or 3 days in Boston at the end. Something to consider is whether or not you want to see Acadia NP, it is a stunning place but it’s a long way out from the rest of New England’s top foliage spots. If you don’t include Acadia, you can spend longer in the fall color hotspots of Stowe, Woodstock and Manchester in VT, plus Franconia Notch, Kancamagus Highway and Lake Winnipesaukee in NH. Let us know if you have any more questions and best of luck with planning!

We are planning a trip to Maine in the fall of 2023 for our 40th anniversary for a total of 7 days. We would be interested in mainly leaf peeping,Arcadia NP, sight seeing/boat tours, driving the back roads and easy hikes. I really like the coast. Now that I have run across this post, I am rethinking our trip. What city should we fly into? Do you recommend spending 2 days in Arcadia NP? Should we hit some of the areas you mentioned in NH? I don’t think we have time to do your whole itinerary in 7 days. Your thoughts?

Hi Randi, glad to hear you have a trip planned to Maine for your 40th anniversary – congrats! Honestly, 7 days isn’t enough time to be rushing around New England trying to cram in everything. If you like the coast and you want to do Acadia, why not fly into Portland in Maine and slowly drive up to Bar Harbor via the back roads? Acadia is great but it is touristy and expensive, plus you won’t get the best fall colors (when compared to NH or VT). Boothbay Harbor is a nice place to stop between Portland and Bar Harbor, and you can do whale watching tours right out of the small town. If Portland doesn’t work for flight times or prices, Boston will be your best bet. Let us know if you need any more help before you travel next year.

Hi. I’m glad I found this. We are planning our 50th Anniversary to see Vermont and Maine in late September. Is it possible to stay in one place and drive to see the sights? We don’t want to keep changing hotels. This is a lifetime dream for us. Thank you.

Hi Jan, congrats on your 50th anniversary! Without knowing exactly which places in Vermont and Maine you want to see, it is possible to stay in one place but that would mean quite a lot of time spent in the car. If you have a 50/50 split, maybe stay somewhere in New Hampshire in the middle? Or if you plan to spend more time in VT, stay somewhere just inside VT near the NH border? Somewhere near Franconia NH might be a good fit so you are central to most of the fall hot spots and far enough North to see peak colors at the end of September. Have a great time!

Great article! While planning and researching for our New England Fall Foliage Adventure we saw right away that trying to predict “peak” conditions was a difficult proposition, at best. With that in mind and because we have a bit of time on our hands we decided our adventure would be from mid September to mid October 2022. We have booked all of our accommodations and now it’s all about deeply researching the areas and filling in the days. Finding your well written and in depth blog helped confirm our research was spot on and added to our happiness that we are actually going to pull this off. Plus, now we have an excellent study guide to boot! Bring on the trails, the mountains, the breweries, the lobster, cheese, cider donuts, Octoberfests and even the rain! Thank YOU and keep up the fantastic and insightful work!

Hi Jeff, thanks for getting in touch and we are so happy to hear you have planned a full month up in New England! Your list of activities is spot on – hiking, scenery, fall colors, food and beer … recipe for a perfect trip! Good luck filling in the days and hopefully you’ll get optimal weather conditions leading into the peak, just remember to keep an eye on the peak fall colors tracker when you are on site in New England. Have a wonderful trip!

Hello! This post is really very useful! We are planning to go to New England from September 30th to October 8th (we have already booked our flight from Italy). Since we would like to spend a couple of days in Boston too, do you recommend to begin with Boston and then start our road trip or to do the other way round? We would very glad if you could give us more details! Thanks a lot!

Hi Simonetta, thanks for getting in touch and we’re happy to hear you will be visiting New England this fall! This is a tough question because nobody can predict when “peak” fall colors will be in each part of New England. You can keep an eye on a live peak foliage tracker and book everything last minute, but that is risky as accommodation will book up. So, we would suggest starting with Boston and then driving up as far North as you will go on your trip (ie Stowe in VT or Franconia in NH) and then working down South to follow the peak. Please let us know if you have any more questions and you might even see us up there somewhere this year! Have a great time 🙂

I’m so happy to have found your blog post. I know how much time and effort goes into planning these type of trips, so I appreciate you writing about it and sharing it. We are looking at doing a mix of rural/city for both NH, VT, and ME. Looking closer to a 10 day trip and flexible on the dates. Would you say the hikes are fairly easy, medium, or difficult? Do you think looking into Air BNB’s out there would be better vs. hotels?

Hi Ani, thanks for getting in touch and we’re glad to hear you have a trip planned for VT, NH and ME. There are countless hikes spanning the difficulty range on this road trip route, so you do have a lot of flexibility over how long you want to spend hiking and how hard the trails are. Artists Bluff is short but has a steep climb, so we would say it is moderate but well worth it. Flume Gorge is easy and shouldn’t be missed. Acadia (if you make it that far) has a host of easy through hard hikes. Lake Winnipesaukee has plenty of hikes to suit all. If you’re looking for hard hikes take on Mt Washington or Mt Mansfield, tallest in NH and VT. You’ll likely only be spending one night or a maximum of 2 at any given place so we would say go for hotels. AirBnB’s are great for uniqueness and meeting people but for one night they are always more expensive with cleaning fees / service fees etc. By all means check prices and see if you can find any good deals or special places but we will be sticking to hotels ourselves the next time we are in New England. Let us know if you need any more help and have a fantastic trip!

Great information, love your post! We have never been to New England and would like to go see the fall colors in late Sept. or Oct. We also want to spend some time in Boston and Cape area. We are flexible on dates and number of days in itinerary. We would be interested in some hikes. After looking at you post I’m thinking Vermont and New Hampshire might work after seeing Boston. Can you help with an itinerary? We would be flying from San Diego, CA. Would appreciate any information! Thank You!

Thanks for getting in touch, Marilen – we’ll respond through email so we can provide more information.

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5 best fall foliage cruises in New England, Canada and beyond

If you feel left out whenever your social media feeds blow up with beautiful pictures of fall foliage, you probably should plan your own leaf-peeping trip. Sure, you could arrange an epic road trip, complete with traffic jams and overpriced, overcrowded tourist traps. Or, you could take a fall foliage cruise.

From a cruise ship, you can enjoy the autumnal hues of the Canadian and New England coastline as you sail between northeastern U.S. home ports like New York and Boston and Canada's Montreal or Quebec City. Book shore excursions for a more relaxing day out; the bus driver will navigate the traffic along tree-lined byways to scenic vistas, and your mealtimes will be prearranged (or held on board your ship's multiple dining venues).

If you'd rather explore fall's colors outside of the Northeast, a few cruise lines will take you to fall foliage destinations in other parts of the U.S., too.

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You'll want to book your Canada and New England cruise at least six months (if not a year or more) in advance for the best pricing and availability. Here, we present the five best fall foliage cruises you should consider in New England, Canada and beyond.

7-day Canada and New England Discovery cruise on Holland America

Holland America 's 1,964-passenger Zuiderdam is a delightfully midsize ship, so you don't have to worry about crowds as you sail between Boston and Quebec City. The ship starts sailing this route in late August, but for the best leaf peeping, you'll want to book one of the two October departures.

Ports of call include Charlottetown, Prince Edward Island; Sydney and Halifax, Nova Scotia; and Portland or Bar Harbor, Maine. Take your pick of scenic drives or strolls through gardens or along hiking paths, camera at the ready. On board, spend your evenings rocking out to live music or enjoying a leisurely meal of steak or seafood at the Pinnacle Grill.

Best for : Holland America attracts mainly retirees and couples who appreciate the line's focus on fine dining and live performances. Zuiderdam's itinerary is ideal for anyone who doesn't mind flying in and out of different cities in order to travel farther north into Canada than the one-way sailings.

Related: 11 best cruises to Canada and New England

7-day Canada and New England cruise on Princess Cruises

For an easy round-trip New York cruise that leans more into New England than Canada, consider Princess Cruises ' weeklong October sailings on the 3,660-passenger Enchanted Princess. Choose from itineraries with four or five ports, including Newport, Rhode Island; Boston; Bar Harbor; Halifax; and (only on certain sailings) Saint John, New Brunswick.

If seascapes are your thing, don't miss the beautiful coastal landscape by the Bay of Fundy (from Saint John) or Peggy's Cove in Nova Scotia. Head to the hills in Bar Harbor for elevated views, or escape to sea with a harbor cruise from Newport.

Best for : Princess Cruises also attracts mature couples and lovers of classic cruising, but the 2019-debuted Enchanted Princess is much larger and bigger than Holland America's Zuiderdam. Kick back with the line's signature Movies Under the Stars (complete with blankets for fall nights in New England), or enjoy multiple specialty restaurants devoted to Italian specialties, steakhouse fare and seafood. Bundle up for a romantic breakfast on your balcony while the colorful coastline passes by.

Related: The best time for a Canada and New England cruise

7-night Canada cruise on Royal Caribbean

Combine an easy Boston round-trip sailing with a fall foliage cruise focused more on Canadian than New England ports with Royal Caribbean 's seven-night voyages on the 2,191-passenger Jewel of the Seas, setting sail in September and October 2024, and 2,142-passenger Brilliance of the Seas, departing in September and October 2025. Most itineraries call in Portland, Maine; Saint John; Sydney; and Halifax.

The ships are among Royal Caribbean's older and smaller ships, so don't go in expecting a humongous megaship with wild top-deck amenities (a good thing or not, depending on your style). You'll still find plenty of dining options (including Izumi for Japanese cuisine and Giovanni's Table for Italian), the line's signature circular Viking Crown Lounge and — perfect for fall weather — an indoor, adults-only solarium.

Best for : Royal Caribbean fans seeking a midsize ship experience with fewer children on board should book this cruise. Anyone looking for a round-trip cruise to Canada that doesn't require a passport will appreciate the convenient Boston departure port (with plenty of beautiful fall foliage on its own) and three port calls in Nova Scotia and New Brunswick.

Related: Canada and New England cruise packing list: What to pack for every season

7-night Puget Sound and San Juan Islands cruise on American Cruise Lines

Canada and New England aren't the only regions of the U.S. known for their fall foliage. American Cruise Lines offers several small-ship sailings in October to other leaf-peeping regions, including the Hudson River Valley, the Upper Mississippi and the Chesapeake Bay.

But for something completely different, why not try the line's seven-night, round-trip Puget Sound and San Juan Islands cruise from Seattle on the 90-passenger American Spirit or the 170-passenger American Constellation?

Your itinerary will take you to Anacortes, Friday Harbor, Port Angeles (gateway to Victoria, British Columbia, and Olympic National Park), Port Townsend and Poulsbo, Washington, with a day spent cruising around the San Juan Islands. Take advantage of the Fidalgo Island walking trails near Anacortes, and don't miss the photogenic Deception Pass nearby. Gaze at the Olympic and Cascade mountains in their fall glory, and enjoy the fall weather in historic waterfront towns.

Best for : Travelers looking for a different destination for their fall foliage cruise, but also cruisers who prioritize time on shore over time on the ship. American Cruise Lines' ships are tiny, just four to six decks, with amenities limited to a restaurant, a couple of lounges, small fitness areas and a sun deck, perhaps with a putting green. Be prepared to entertain yourself in the evenings — or go to bed early so you're energized for a full day in port nearly every day. Also, know that these ships generally draw an older retiree crowd.

12-day Canada and New England Fall Foliage cruise on Seabourn

Smaller ships can visit more off-the-beaten-path ports than their big-ship counterparts. Seabourn 's 458-passenger Seabourn Quest (2024) and Seabourn Sojourn (2025) sail 12-day cruises between New York and Montreal. Itineraries vary slightly by sail date, but visit several destinations in Quebec, including Trois-Rivieres, Quebec City, Baie-Comeau and Saguenay, with scenic cruising along the Saguenay Fjord. The ship also visits Charlottetown, Prince Edward Island; and Halifax, Nova Scotia; it stops at a couple of American ports, too, such as Newport, Rhode Island, and Boston, Martha's Vineyard or Provincetown, Massachusetts.

This is also one of the best fall foliage cruises if you're looking for an all-inclusive voyage in luxurious surroundings. On Seabourn Quest, every cabin is a suite with a view (not to mention a walk-in closet and spacious bathroom with tub). You can enjoy gourmet cuisine, complimentary wine and cocktails and a friendly crew that will go above and beyond for you.

Best for : Luxury lovers who wish to be pampered on their leaf-peeping vacation will enjoy this nearly two-week cruise around Canada and New England. The extended itinerary features several days at sea to enjoy the ship's spa or delicious afternoon tea service, as well as some lesser-visited ports and, on select departures, an overnight in Halifax. It's ideal for travelers who want to make the most of their fall Northeast trip.

Bottom line

You might be surprised by how many choices you have for late-September and October fall foliage cruises. In addition to Seabourn, all the major luxury cruise lines dedicate a few cruises to this region, including such lines as Silversea Cruises , Regent Seven Seas Cruises , Windstar Cruises , Oceania Cruises and Crystal . Big ships like NCL's Norwegian Breakaway and Getaway also get into the leaf-peeping action.

Here, we've picked the best fall foliage cruises for different itinerary configurations and ship styles. They might be our favorites, but only you know which combination of ports and onboard experience is the perfect match for your travel style.

Planning a cruise? Start with these stories:

• The 5 most desirable cabin locations on any cruise ship
• A beginners guide to picking a cruise line
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• The ultimate guide to what to pack for a cruise
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Protect Your Trip »

Icon of the seas: the best dining, amenities and more on royal caribbean's new ship.

This family-friendly megaship features plenty of activities, entertainment and restaurants.

Icon of the Seas

Courtesy of Royal Caribbean International

Key Takeaways

• Icon of the Seas is the largest cruise ship in the world, with 18 passenger-accessible decks, eight different neighborhoods and 2,805 staterooms.
• Think of Icon of the Seas as an all-in-one adventure vacation contained on a ship. Young families and energetic travelers will enjoy it most.
• Itineraries originate from Miami , sail to destinations around the Caribbean and include a stop at Royal Caribbean's private island , Perfect Day at CocoCay.

If you have any degree of interest in traveling or cruising, chances are you've heard the buzz around Icon of the Seas. Another record-breaking ship by Royal Caribbean International , Icon of the Seas debuted on Jan. 27, 2024, as the largest cruise ship in the world. It is epic in every sense, featuring 18 cruiser-accessible decks and stretching 1,196 feet from bow to stern.

With greatest-of-all-time soccer player Lionel Messi as the ship's godfather, the Icon of the Seas is truly iconic. Messi brought the entire Inter Miami team along for the opening ceremony and the big reveal of the team's new Royal Caribbean-sponsored jerseys. I was fortunate enough to attend this star-studded ceremony as part of the press preview sailing in the days leading up to the ship's grand debut to the public. It was everything I thought it would be and more, and nobody could have been more appropriate than Messi to send this ship on her maiden voyage.

Boarding a ship of this size can seem overwhelming, but not when you understand the layout. Icon of the Seas is broken up into eight distinct neighborhoods: AquaDome, Central Park, Thrill Island, Chill Island, Royal Promenade, The Hideaway, Suite Neighborhood and Surfside, a neighborhood built for young families looking for nonstop fun and kid-approved eats and treats.

In addition to these public areas, there are 2,805 staterooms spread across 12 decks. Icon of the Seas' capacity maxes out at 7,600 passengers and 2,350 crew members, but with the plethora of public spaces and variety of things to do and see, you can choose your own adventure without encountering more crowds than you want to.

Find your perfect cruise

Skye Sherman

Icon of the Seas itinerary

During its inaugural 2024-2025 cruising season, Icon of the Seas offers seven-night eastern or western Caribbean adventures from Miami, stopping at a variety of tropical destinations. All sailings include a stop at Royal Caribbean's award-winning private island, Perfect Day at CocoCay, in the Bahamas . Other destinations include Basseterre, St. Kitts & Nevis ; Roatan, Honduras; and Cozumel, Mexico .

During the 2025-2026 cruising season, new destinations will include Puerto Plata, Dominican Republic ; San Juan, Puerto Rico ; Labadee, Haiti; Costa Maya, Mexico; and Charlotte Amalie, St. Thomas (part of the U.S. Virgin Islands ). All sailings will originate from Miami.

No matter your Icon of the Seas itinerary, you'll visit beautiful places – but you can expect to feel torn about spending any time off the ship, because it's just that jampacked with things to do.

Who should sail on Icon of the Seas?

Icon of the Seas appeals not so much to a demographic as to a psychographic; you're going to need to be someone who likes to live life in all caps. Royal Caribbean set out to create "the world's best vacation" contained on a ship, so Icon of the Seas is for anyone who would enjoy the combination of a beach trip, a resort stay, a water park adventure and island-hopping.

Fun-loving travelers and families with kids of varying ages will do best on this ship; it feels a little bit like Disney World with over-the-top everything and a truly massive sprawl. Older travelers who prefer a more quiet, refined experience may want to opt for a less kid-friendly ship. Still, even couples without children will find plenty of fun adult-friendly things to do and romantic places to tuck in.

The Royal Promenade can be quite loud and buzzy, but simply relocating to another onboard neighborhood can completely shift the vibe. Also, keep in mind that the ship really is huge, and walking from end to end can be a hike, so those with limited mobility or endurance might want to look into a smaller ship.

Icon of the Seas prices are high in its opening season, but cruisers with big dreams and small budgets can expect rates to drop by the time the next ship in the series debuts.

The stateroom

With a ship this overstimulating, it's imperative that your stateroom is a haven. Luckily, Icon of the Seas offers peaceful rooms, many of which feature ocean or Central Park neighborhood views. Cruise ship accommodations are stereotypically compact – even cramped – but the floor-to-ceiling panoramic windows in Icon of the Seas' cabins (with the exception of the windowless interior rooms) lend an airy, open feel. The cabin layouts are also optimized to provide the maximum amount of storage, floor space and comfort.

Stateroom decor is mildly nautical- and tropical-themed, with calming hues that mimic the scenery outside your window (think blues, beiges and whites). High-tech elements include smart TVs, LED mirrors and the ability to control many aspects of your room from an app.

My husband and I stayed in an Ocean View Large Balcony Stateroom, a 204-square-foot refuge from the hustle and bustle of the ship (the balcony adds another 65 to 70 square feet). This room type can sleep up to four people with a sofa bed for one or two; the room also features twin beds that convert to a king bed for couples.

My husband is 6 feet, 3 inches tall, and we were comfortable in our room, even though our quarters included a large bed, a bathroom, a sofa and a desk. We loved sitting on our private balcony and watching the deep blues of the Atlantic Ocean flow by.

If money is no object, the Ultimate Family Townhouse – an over-the-top eight-guest, three-story pad with a private whirlpool on the balcony, three bathrooms, a slide that connects the second and main levels, an in-suite cinema, a dining room and a kitchenette – looks epic. But keep in mind, it costs nearly $100,000 for the week.

The Sunset Corner Suites (about one-fifth of the cost of the Ultimate Family Townhouse, but still expensive) are also pretty sweet, with a wraparound balcony and a bed facing the sea.

Luckily, not all rooms break the bank; with four main stateroom categories (suite, balcony, ocean view and inside) and 28 subcategories, there's something for everyone.

Best amenities on Icon of the Seas

It's almost impossible to run out of things to do aboard Icon of the Seas.

For thrill-seekers, the largest water park at sea – Category 6 – features the Frightening Bolt (the tallest waterslide on a ship) and the Pressure Drop (the first open freefall waterslide on a cruise vessel).

If you've tired of the seven swimming pools, six waterslides, laser tag, mini-golf, rock climbing wall, escape room, sports courts, outdoor decks, theater, spa and all-day programming, simply take a stroll down the Royal Promenade for Las Vegas -style people-watching. The Royal Promenade has 15 restaurants, bars and lounges, as well as a Starbucks that seems to have a line no matter what time you go. The neighborhood feels a bit like a shopping mall … if a shopping mall had floor-to-ceiling ocean views made possible by the world's largest kinetic art sculpture.

The Pearl, a feat of engineering, is one of the most unique aspects of the ship's design. This art piece is actually a load-bearing structure supporting three decks, but it looks and feels like an interactive art experience designed solely for the enjoyment of guests. The multisensory immersive structure has 3,000 kinetic panels and moody ever-changing lighting. It is one of the first things guests will see when they walk on board, as it stretches from the Royal Promenade up to Central Park.

My husband and I spent most of our time at the FlowRider surf simulator – his favorite amenity – but we made sure to leave time for Taylor Swift trivia at Spotlight Karaoke and the superhuman stunts of the Aqua Theater show, a must on any Icon of the Seas voyage. The ship even has a massive ice arena called Absolute Zero for ice skating (the 20-minute sessions are complimentary) and impressive shows.

We also loved lounging in The Overlook Bar & Pods, an area at the very front of the ship (behind the AquaDome) that features two levels of floor-to-ceiling wraparound windows. It felt airy and open, which can't be said about many cruise ship interiors.

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Best dining venues on Icon of the Seas

There are more dining options aboard Icon of the Seas than you can fit in on a seven-night cruise – but you can give it the old college try. Thirteen of the dining venues are complimentary, while 14 are specialty restaurants (which cost extra; fees vary). There are also 18 bars and lounges.

The best meal we experienced on the ship was at the Chops Grille specialty eatery. When we spotted Royal Caribbean CEO Jason Liberty and a group of bigwigs at a table next to us, we knew we were in the right place. We loved sitting outside and enjoying the breezes of Central Park while we chowed down, but you can eat indoors for an elegant steakhouse experience and a view of the open kitchen and butcher's display, which shows off specialty cuts like high-grade wagyu and bone-in tomahawks.

While I'd never turn down a swanky steak dinner, grabbing quick poolside bites at El Loco Fresh and indulging in some food hall-style grazing at AquaDome Market were equally enjoyable. We also had no complaints eating several meals at Windjammer, the classic complimentary cruise ship buffet.

Even though we don't have children, we stopped into Surfside Bites for a very kid-friendly meal, complete with soft serve ice cream cones from Sprinkles (because no cruise is complete without soft serve). We didn't try anything from the open-air, lemonade stand-inspired Lemon Post bar, but its menu of cocktails and mocktails looked delicious.

And since you're on vacation, be sure to check out the milkshake bar Desserted, where the sugary creations are as photo-worthy as they are decadent. They're worth the upcharge.

Best excursions on Icon of the Seas

Depending on what's on your Icon of the Seas itinerary, you may be able to book activities like snorkeling, scuba diving, tropical jungle adventures, visits to Mayan ruins, volcano hikes, rainforest zip lining, relaxing beach days or cultural immersion tours.

Note that Royal Caribbean features the same options on many of its other Caribbean cruises; none of the excursions on offer are exclusive to Icon of the Seas.

Because our press preview sailing only visited Perfect Day at CocoCay, we did not experience any of the shore excursions. Royal Caribbean's private island in the Bahamas was plenty of fun, even though we didn't plan anything in advance.

If we had made plans, we would have liked to check out the Up, Up and Away tethered hot air balloon, which wasn't running that day, and the overwater cabanas at Coco Beach Club, which were all booked. Thrill Waterpark (which features the tallest waterslide in North America), Oasis Lagoon (the largest freshwater pool in the Caribbean) and the adults-only Hideaway Beach are other highlights of Perfect Day at CocoCay.

Overall impressions of Icon of the Seas

Royal Caribbean seems to be focused on superlatives. It has the biggest, best, tallest, largest and most of everything – especially when it comes to Icon of the Seas. If you like jampacked, adventurous vacations that squeeze a lot of adventure and relaxation into one memorable week, Icon of the Seas is probably for you.

While I love seeing Royal Caribbean push the limits of what cruises can be, the ship may almost be too big for some. It's an all-out Vegas-esque vessel that feels more like a floating city; you will probably forget (more than once) that you're not on dry land.

That's not necessarily a bad thing – if Icon of the Seas looks fun to you, it probably will be – but my husband and I tend to gravitate more toward authentic, immersive, on-the-ground cultural experiences when we travel. While Icon of the Seas is a lot of things, it's not that. We had a fantastic time and have already started planning a future Royal Caribbean cruise with a group of friends and family, but we also sympathize with the anticruisers of the world. Vacationing does not a traveler make.

Still, the shows are entertaining, the service is attentive, the music is jamming, and the architecture and design are incredibly impressive. I have no real complaints and suspect that most cruisers will have the time of their lives on Icon of the Seas – exactly as the minds at Royal Caribbean envisioned when they dreamed up this iconic ship.

Why Trust U.S. News Travel

Skye Sherman has been cruising since childhood, when her parents took her on her first cruise through the Caribbean. She has sailed various ocean cruise lines, gone off the grid for a six-day riverboat expedition deep into the Amazon River and even planned a European river cruise with 48 of her closest family and friends. She's a fourth-generation Floridian and hopes to visit every country in the world during her lifetime. She covers travel and lifestyle topics for major publications including U.S. News & World Report.

You might also be interested in:

• The Newest Royal Caribbean Ships
• Royal Caribbean vs. Carnival
• The Largest Cruise Ships in the World
• The Best New Cruise Ships
• The Best Cruise Insurance

Tags: Travel , Cruises , Royal Caribbean Cruises

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