The Perfect 7 Day New England Fall Road Trip Itinerary (+Scenic Drives!)🍁2024

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.

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:

• Book Accommodation Early:
  • Make reservations for accommodations and popular attractions well in advance, as this is one of New England’s busiest times of the year.
• What to Wear:
  • 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.
• Drive with Caution:
  • 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.
• Camera and Binoculars:
  • 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!
• Local Cuisine:
  • Don’t leave New England without indulging in its fall culinary delights, including apple cider donuts, pumpkin pie, and hearty clam chowder.
• Offline Maps:
  • 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.
• Respect Nature and Wildlife:
  • Admire the scenery while being mindful of the environment; practice leave no trace principles and respect wildlife habitats.
• Road Trip Safety Essentials:
  • 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.

1. 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.
2. 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
3. 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 Elms
• 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!

Points of Interest:

• 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
• Best Time to Go: September to Mid-October

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!

Points of Interest: 

• 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.

Points of Interest: 

• 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
• Shore Path – Bar Harbor

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!

Points of Interest:

• 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
• Best Time to Go: September to Early November

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.

Points of Interest:

• 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!

---