Experiencing a New England fall is like stepping into a coloring book. From colorful woodland paths to decorated charming villages and towns, following a New England fall road trip itinerary is the best way to experience that autumn magic you dream about!

During fall 2021, I did a memorable 7-day New England fall road trip where I got to experience the best of fall foliage in four different U.S. states – New Hampshire’s White Mountains, Vermont, the Berkshires of Western Massachusetts and the Catskills of New York. I am excited to share a thorough New England fall itinerary to follow as you plan your leaf-peeping trip for this year!

(Discover the best New England fall foliage tours for 2022.)

I did my Northeast road trip with Hannah Liz Weaver and we had the best time enjoying every scenic drive and small town! As you are planning your New England fall foliage trip, I recommend following my 1-week itinerary listed below in the article.

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Traveling to the East Coast for a Fall Road Trip:

Since this New England fall road trip itinerary starts in New Hampshire’s White Mountains, you can either take a flight or drive to this colorful area. The closest international airport to the White Mountains of New Hampshire is Boston Logan International Airport in Boston, Massachusetts.

There is also a regional airport you can fly into called Manchester-Boston Airport in Manchester, New Hampshire. You can find affordable flights through Skyscanner.

One of the best ways to see fall foliage in New England is by driving! Since I came from my home in Northern New Jersey, I drove my own car five hours north to Waterville Valley, New Hampshire. On the way, I picked Hannah up from Boston Logan since she flew from Dallas.

Whether you take your own car or hop on a flight to see the foliage, you will need a vehicle to get around New England and Upstate New York. From the airport, I recommend renting a car.

(Click here if you are planning to road trip around the United States and want to rent an RV.)

If you want to extend your New England road trip, I recommend spending a weekend in Boston and also visiting the Halloween town of Salem.

Where to Stay during a New England Fall Road Trip:

Throughout New England, you can find many great accommodations ranging from all different budgets. In addition, you can also find perfect rental properties in this area.

Below are the accommodations Hannah and I stayed in during our 7-day New England fall road trip:

2 nights in Waterville Valley, New Hampshire: We stayed at The Valley Inn in Waterville Valley, New Hampshire.

1 night in Woodstock, Vermont: We stayed at Mountain Meadows Lodge in the nearby town of Killington, Vermont.

2 nights in the Berkshires, Massachusetts: We stayed one night at the Red Lion Inn in Stockbridge, Massachusetts and one night at Miraval Berkshires in Lenox, Massachusetts.

2 nights in the Catskills, New York: We stayed at Getaway House in the Eastern Catskill town of Catskill, New York.

The Best New England Fall Road Trip Itinerary:

There isn’t a more perfect time to visit the New England states than in late September and early October. This is usually the best time to see fall colors and the weather is perfect for outdoor activities!

If you want to ensure you experience peak foliage, use this New England tracker. You could also experience beautiful fall foliage in the middle of the month, but most of it is past its peak by late October.

Day 1: Arrive in New Hampshire’s White Mountains – The Best of Fall Foliage in New England

Discover the best fall foliage weekend in NH’s White Mountains.

Hotels to Stay at Surrounding White Mountain National Forest:

Luxury Accommodation: Omni Mount Washington Resort, Bretton Woods, NH

Boutique Accommodation: Stonehurst Manor, North Conway, NH

Mid-Budget Accommodation: Sugar Hill Inn, Sugar Hill, NH

Budget Accommodation: Town and Country Inn and Resort, Shelburne, NH

After arriving in New Hampshire, I recommend checking into your accommodation and settling in. You will be hungry from there, so I suggest enjoying a nice lunch or dinner at Covered Bridge Farm Table. It is a cozy American restaurant overlooking the scenic Penigewasset River and the historic Blair Covered Bridge. (Both New Hampshire and Vermont are known for their iconic covered bridges.)

Enjoy Peak Fall Colors at Flume Gorge:

If you have time on your first day, I advise checking out Flume Gorge. It is known as one of the best jewels of Franconia Notch State Park. Flume Gorge, formed during the Ice Age, features a 2-mile loop trail where you can enjoy stunning nature.

Day 2: Explore Franconia Notch State Park – The Best of Peak Foliage

Enjoy all the beautiful foliage during the fall season in Franconia Notch State Park on your second full day in New Hampshire! First, I suggest enjoying an excellent breakfast at Polly’s Pancake Parlor in Sugar Hill before conquering the hiking trails.

What makes Franconia Notch State Park iconic is that the Appalachian Trail runs through it.

Artist Bluff Trail: The Best Hiking Trail during Fall in New England

After breakfast, a great hike to enjoy in Franconia Notch State Park is the Artist Bluff trail! This great hiking trail is one of the best spots to see fall colors during your New England road trip itinerary.

The Artist Bluff trail is a 1.5-mile moderate loop trail that includes two overlooks, some rock scramble and beautiful woodland paths. It is a heavily trafficked hike, especially during the fall.

What is great about doing the Artist Bluff trail during autumn is that there is an overlook offering the best of New Hampshire’s fall foliage over the entire Franconia Notch valley.

Cannon Mountain Aerial Tramway: One of the Best Things to do in New England

If you don’t want to hike, I recommend riding the Cannon Mountain Aerial Tramway in the State Park. It’s a great way to enjoy the colorful foliage!

Cannon Mountain is a 4,080-foot peak. When you take the tramway to the summit, you can enjoy 360-degree views of the White Mountains and its stunning fall foliage. You can also see up to four states and two countries – New Hampshire, Maine, Vermont, New York and Canada!

The tram runs between 9 am to 5 pm from late May through mid-October, but it is subject to change based on weather. It costs $25 USD to take the aerial tramway for adults and teens 13 years and older; $20 USD for children ages 6-12 and it is free for young children ages five and under.

For lunch, a great place to visit is Littleton Freehouse Taproom & Eatery which serves local craft beer and cider along with New England staples like clam chowder. After your meal, I suggest strolling around the charming town of Littleton and checking out some of the shops.

If you don’t have your own vehicle, you must enjoy the scenic Mount Washington Cog Railway, which takes you to the highest mountain in the Northeastern United States.

Another area to go hiking and enjoy the most beautiful autumn foliage is Crawford Notch State Park!

Kancamagus Scenic Byway: Best Scenic Route in NH’s White Mountains

In the afternoon, drive around and enjoy the best views of the White Mountains’ fall foliage on the Kancamagus Scenic Byway. This 34.5-mile drive along Route 112 offers the best viewing areas for leaf peepers and can be added to all New England fall road trips!

Please note that you must have a full gas tank before driving on Kancamagus Highway. Once you drive past the town of Lincoln, there are no gas stations or cell phone reception.

Along the Kancamagus fall foliage drive, you’ll admire some of the best views of the White Mountains during the fall season. You’ll see the beautiful Swift River, Sabbaday Falls, Lower Falls and the Rocky Gorge. There are also plenty of overlook spots to pull over and enjoy stunning views.

Once you’re finished completing the Kancamagus Scenic Byway during your New England fall road trip itinerary, I recommend making a pit stop at Matty B’s in Bartlett to enjoy some pizza.

Day 3: Wander Around the Perfect New England Fall Town of Woodstock, Vermont

Discover the best places in Vermont to see fall colors.

Hotels to Stay at in Woodstock:

Luxury Accommodation: Woodstock Inn & Resort

Boutique Accommodation: 506 on the River Inn

Mid-Budget Accommodation: The Woodstocker B&B

Budget Accommodation: Comfort Inn White River Junction

On the third day of your fall road trip in New England, wake up early and drive to Woodstock, Vermont. It took us over an hour and a half to drive from Waterville Valley, NH to Woodstock, VT. After checking into your hotel, stroll through the charming autumn village!

Please note that Woodstock is a popular destination during autumn due to its charm and historical sites. It’s best to book your accommodation in advance!

Woodstock, Vermont: The Most Charming Town to Visit during a New England Road Trip

After enjoying a late breakfast at Mon Vert Café, walk to the Woodstock Inn. This beautiful place is a luxury hotel with fall décor and plants to enjoy. At Woodstock Inn, you can make a reservation at one of the four restaurants or attend a wine or cooking class. There are also fireplaces around the hotel for you to cozy up and enjoy a glass of wine in front of.

As you stroll around Woodstock, VT, check out the covered bridges surrounded by beautiful fall colors. Even if you don’t have time to see a lot of covered bridges during your New England fall trip, I suggest checking out the Middle Covered Bridge, which is across from the Woodstock Inn, and the Taftsville Covered Bridge that is right off of Route 4, which is the main road that takes you into the heart of town.

Another beautiful spot to see in Woodstock that you must include in your New England fall road trip itinerary is Sleepy Hollow Farm. It is a short drive from the heart of town and one of Woodstock’s most “Instagrammable” spots, so be prepared for crowds when you visit.

Sleepy Hollow Farm isn’t a typical fall farm where you go pumpkin picking and enjoy a hayride. It dates to the 1780s when two young brothers from Connecticut left their family farm for a new life in Central Vermont. They weren’t pioneers but were known for their milking herd and chickens. They would deliver eggs to homes around Woodstock and the surrounding towns.

For dinner in Woodstock, I suggest enjoying a lovely fall meal at 506 Bistro & Bar at 506 on the River Inn! This cozy, farm-to-table restaurant boasts an incredible seasonal menu with craft cocktails to enjoy. Each dish is inspired by fresh, high-quality ingredients from local Vermont farms.

Day 4: Follow Along a Mini Vermont Road Trip Itinerary

Even though I made my way to the Berkshires on the fourth day of my New England fall road trip itinerary, I recommend spending another night in Woodstock and enjoying a day trip to Smugglers’ Notch and Stowe Mountain Resort.

Before heading up north, I suggest fueling up at Soulfully Good Café in Woodstock. It is a great organic restaurant that has mouthwatering plates.

Smugglers’ Notch:

Situated less than two hours north of Woodstock, Smugglers’ Notch is the perfect fall place to visit during a Vermont road trip itinerary. It boasts the beautiful Green Mountains with stunning fall colors and there are a lot of great half-day and mini hikes to enjoy!

I recommend visiting Smugglers’ Notch before heading to the quaint fall town of Stowe. Some of the best hikes in Smugglers’ Notch are on Mount Mansfield, the highest peak in Vermont. There are also great waterfall hikes like Bingham Falls and Moss Glen Falls.

Stowe, Vermont: The Best Place to do Fall Activities in New England

When you get to Stowe in the afternoon, you must visit Cold Hollow Cider Mill in Waterbury Center. It is a fun fall spot with a general store, country market, bakery, restaurant and cidery. The surrounding area also boasts breathtaking views of the Green Mountain National Forest.

Cold Hollow Cider Mill is the perfect place to enjoy homemade apple cider donuts, a staple baked good during fall in the Northeast. If you’ve never tried a cider donut, it is a cake donut with cinnamon sugar, powdered sugar or baked plain.

At the market, you can also purchase fresh Vermont maple syrup; a variety of pies; pumpkin, apple and maple butter; pancake mixes and souvenirs.

I recommend eating at Cold Hollow’s Luncheonette for lunch and doing a fall cider tasting. They offer great ciders to choose from and taste, ranging from sweet, fruity, dry and seasonal.

Afterward, visit the Ben & Jerry’s factory for a nice treat! During a fall road trip to Stowe, it is a must to do a factory tour while tasting some of Ben & Jerry’s most renowned ice cream flavors!

Before heading back to Woodstock, take a fun ride on the Gondola Skyride to the summit of Mount Mansfield, Vermont’s highest mountain. It is where you can see some of the best fall foliage in Vermont!

Stowe’s Gondola Skyride operates during the daytime and the price for one adult and teenager, ages 13 and older, is $37 USD and the price for a child, aged 5-12, is $26 USD. Young children under five can ride the gondola with a parent or guardian.

When you return to Woodstock, enjoy dinner and drinks at Dr. Coburn’s Tonic. It is a fun pub with great craft cocktails, flatbreads, burgers and more.

Day 5: Experience Fall in the Berkshires of Western Massachusetts

Read all about fall in the Berkshires.

Hotels to Stay at in the Berkshires:

Luxury Accommodation: The Barrington, Great Barrington, MA

Boutique Accommodation: Hotel on North, Pittsfield, MA

Mid-Budget Accommodations: The Black Swan Lee – Lenox, Lee, MA

Budget Accommodation: Holiday Inn & Suites, Pittsfield, MA

Monument Mountain in Stockbridge, Massachusetts: Best Place to See Fall Foliage in the Berkshires

It took us over two and a half hours to drive from Woodstock, VT, to Stockbridge, MA. When you arrive in the Berkshires, I recommend stopping in Lee first.

A great place to get an excellent breakfast or brunch is at Starving Artist Creperie and Café. From there, head to Stockbridge and do the Hickey and Peeskawso Peak Loop trail at Monument Mountain.

Overall, the Hickey and Peeskawso Peak Loop trail is one of the best spots to enjoy fall foliage in the Berkshires while you follow along a New England road trip itinerary. It is a 2.4-mile, moderate and heavily trafficked loop trail that features mini waterfalls, streams, rocky hills and overlooks of the colorful mountains of Western Massachusetts.

Enjoy a the Perfect Fall Afternoon in Pittsfield, Massachusetts:

For lunch, head to Pittsfield to savor a delicious meal at District Kitchen & Bar. It is a swanky restaurant that features tasty seasonal plates.

From there, enjoy an afternoon at Balderdash Cellars, where you can do a wine production tour, taste from different bottles, listen to live music, make memories with friends and admire the beautiful fall foliage.

Have a Relaxing Evening in Great Barrington, Massachusetts:

In the evening, head into the town of Great Barrington to enjoy delicious food and drinks. A fun cocktail bar with incredible small plates is Mooncloud Lounge and an excellent restaurant to eat dinner at is Agaves Mexican Grill.

Great Barrington is also a charming town to stroll through and enjoy boutique shopping, live music venues and art galleries.

Day 6: Admire Fall Foliage in the New York Catskills

Discover the perfect Getaway House in New York.

Hotels to Stay at in the Catskills:

Luxury Accommodation: Emerson Resort & Spa, Mount Tremper, NY

Boutique Accommodation: Urban Cowboy Lodge, Big Indian, NY

Mid-Budget Accommodation: Foxfire Mountain House, Mount Tremper, NY

Budget Accommodation: Catskill Mountain Lodge, Palenville, NY

It takes around an hour to get from the heart of the Berkshires in Massachusetts to the heart of the Catskills in New York.

During your New England fall road trip, adding Upstate New York to your itinerary is a must. Even though New York isn’t technically New England, it is still a stunning destination to see fall colors. It is close to many spots in Massachusetts, Vermont and Connecticut.

When you first arrive in the Catskills, a lovely spot to grab breakfast or brunch is in Leeds, NY. Gracie’s Luncheonette is a cute “Instagrammable” café that offers great coffee, a lovely Southern comfort breakfast and an excellent lunch menu.

Hike Kaatserskill Falls and Visit Hunter Mountain:

Next, a picturesque spot to enjoy fall hiking with waterfall views during your Northeast road trip is Kaaterskill Falls in Hunter, New York.

Also situated near this popular spot is Hunter Mountain. It is a ski resort in winter, but in autumn, they host a great Oktoberfest event to enjoy amongst the fall colors.

Wander through the Quaint Town of Tannersville, New York:

In the afternoon, head into the charming Catskills village of Tannersville to enjoy shopping and wine tasting at Hudson-Chatham Winery. (The one in Tannersville is their tasting room. If you want to visit the actual vineyards, it’s located in the town of Ghent.)

This great winery is indoors, making it the perfect fall spot to warm up on a crisp autumn day. During a visit to Hudson-Chatham Winery, you can taste various wines from the Hudson Valley wine region.

At night, a great place to savor a delicious Italian dinner and local craft beer is Rip Van Winkle Brewing Company in Catskill, New York.

Day 7: Wrap Up Your New England Fall Trip

On the final day of your New England fall road trip itinerary, you can enjoy another hike in the Catskills, visit a Hudson Valley winery or explore New York’s capital, Albany. Not far from that area is the breathtaking Lake George.

A great airport to fly home from the Catskills of New York is Albany International Airport.

(No matter what hikes you choose in New England, I recommend that you download the AllTrails app when you have cell phone reception so that you can find the best trail and use it as navigation.)

Enjoy these other awesome fall destinations in New England:

Visiting Salem, Massachusetts during Halloween

Girls Weekend in Boston

Newport, Rhode Island in the Fall

Planning a memorable USA trip? Find more USA travel tips here.

I hope you all enjoyed discovering the best 1-week New England fall road trip itinerary. If you have any questions, please email me at info@browneyedflowerchild.com.

Basic Facts of the United States:

Currency: United States Dollar, Capital: Washington D.C., NH State Capital: Concord, VT State Capital: Montpelier, MA State Capital: Boston, NY State Capital: Albany, NH/VT/MA/NY Time Zones: All are in Eastern Standard Time

*Anything could happen during your travels. Always make sure you are insured in case there are unforeseen circumstances such as lost luggage/theft, natural disasters, personal liabilities and more. Click here to get insured for your next trip.

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