Taylor-Sleepy-Hollow-Farm3

A woman enjoying fall in Woodstock, Vermont

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 for you to follow as you plan your leaf peeping trip for this year!

A woman enjoying fall foliage at Artist Bluff in New Hampshire

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

I did my Northeast road trip with Hannah Liz Weaver and we had the time of our lives! As you are planning your New England fall foliage trip, I recommend following my 1-week itinerary that is listed below in the article.

**Please note that this blog post uses affiliate links meaning that if you make a purchase via my affiliate link, I receive a small commission at no additional cost to you. I only promote and talk about products and services that I have used and like.


Pin the Below Image to Keep Handy

New England Fall Road Trip Itinerary

Traveling around the New England States:

A woman at Sleepy Hollow Farm during a New England fall road trip itinerary

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 the city of 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. During the way, I picked Hannah up from Boston Logan since she flew from Dallas.

Fall foliage in New England

Whether you decide to 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 Northeast Road Trip:

A woman staying at The Valley Inn in New Hampshire's White Mountains during a New England fall

All throughout New England, you can find a plethora of 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.

The Best New England Fall Road Trip Itinerary:

A woman staying at Mountain Meadows Lodge in Killington, Vermont during a Vermont road trip itinerary

Day 1: Arrive in New Hampshire’s White Mountains

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

Hotels to Stay at in New Hampshire’s White Mountains:

A woman staying in Waterville Valley in New Hampshire during a New England fall road trip itinerary

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. From there, you will be hungry, so I suggest enjoying a nice lunch or dinner at Covered Bridge Farm Table. It is a cozy American restaurant that overlooks the scenic Penigewasset River and historic Blair Covered Bridge. (Both New Hampshire and Vermont are known for their iconic covered bridges.)

Flume Gorge:

Flume Gorge in New Hampshire

If you have time in on your first day, I recommend checking out Flume Gorge. It is known as one of the best jewels of Franconia Notch State Park. Flume Gorge, which was 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 beautiful fall colors of New Hampshire's White Mountains

On your second full day in New Hampshire, enjoy all the beautiful fall foliage in Franconia Notch State Park! First, I suggest enjoying a nice breakfast at Polly’s Pancake Parlor in Sugar Hill.

Artist Bluff Trail:

A woman at the top of Artist Bluff trail during a New England fall road trip in New Hampshire

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:

New Hampshire White Mountains with fall foliage

If you don’t want to hike, I recommend riding the Cannon Mountain Aerial Tramway in the State Park. 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 even Canada!

The tram runs between 9am to 5pm 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 5 and under.

For lunch, a great place to visit is Littleton Freehouse Taproom & Eatery that 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.

Kancamagus Scenic Byway:

Driving the Kancamagus Scenic Byway during a New England fall road trip itinerary

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 fall road trips in New England!

Please note that you must have a full tank of gas before you start driving on Kancamagus Highway. Once you drive past the town of Lincoln, there are no gas stations nor cell phone reception.

Along the Kancamagus fall foliage drive, you’ll admire some of the best views of the White Mountains, the 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 enjoying pizza at Matty B’s in Bartlett.

Day 3: Wander Around the Charming Fall Town of Woodstock, Vermont

A woman at Woodstock Inn & Resort in Vermont during fall

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 a little 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!

Woodstock, Vermont:

Checking out the New England town of Woodstock during a Vermont road trip itinerary in the fall

After enjoying a late breakfast at Mon Vert Café, walk over to the Woodstock Inn. This charming luxury hotel has a lot of beautiful fall décor and plants to enjoy. At Woodstock Inn, you can make a reservation at one of the four restaurants or even 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 different 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.

A woman at Sleepy Hollow Farm in Woodstock, Vermont

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 one of the most “Instagrammable” spots in Woodstock, 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 crafted 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

A woman enjoying Halloween decorations in Woodstock, Vermont during a New England fall road trip

Even though I made my way to the Berkshires on my 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.

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:

Fall foliage in Vermont

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 that has 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. There are also great waterfall hikes such as Bingham Falls and Moss Glen Falls.

Stowe, Vermont:

Cider tasting at Cold Hollow Cider Mill in Stowe, Vermont

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 country store and market, bakery, restaurant and cidery.

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

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

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

Visiting Ben & Jerry's during a New England fall road trip itinerary

Afterwards, 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 flavors!

Before you head back to Woodstock, take a fun ride on the Gondola Skyride to the summit of Mount Mansfield, which is 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 prices 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 5 years of age are free to ride the gondola with a parent or guardian.

When you arrive back in 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

A woman staying at Red Lion Inn in the Berkshires during a fall road trip

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:

A woman at the top of Monument Mountain in the Berkshires during fall

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

Pittsfield, Massachusetts:

A woman at Balderdash Cellars in the Berkshires during a New England fall road trip itinerary

For lunch, head to the town of Pittsfield to savor a delicious meal at Mission Restaurant. It is an incredible tapas and wine bar that features 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 all around.

Great Barrington, Massachusetts:

Visiting Great Barrington in the Berkshires during a New England fall road trip

In the evening, head into the town of Great Barrington to enjoy delicious food and drinks. A swanky cocktail bar with incredible small plates is Mooncloud Lounge and an awesome restaurant to eat dinner at is Agaves Mexican Grill. In general, Great Barrington is also a charming town to stroll through and enjoy awesome shopping, live music and art galleries.

Day 6: Enjoy Fall Foliage in the New York Catskills

A woman staying at a Getaway House in the Catskills of New York

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

A fall hike in the Northeast

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, it is a must to also add on Upstate New York to your itinerary. Even though New York isn’t technically New England, it is still a stunning destination to see fall colors and it’s in close driving distance to a lot of spots in Massachusetts, Vermont and Connecticut.

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

Kaatserskill Falls and Hunter Mountain:

Oktoberfest in the Northeast USA

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. During the winter, it is a ski resort, but in autumn, they host a great Oktoberfest event to enjoy amongst the fall colors.

Tannersville, New York:

Wine tasting at Hudson-Chatham Winery in the Catskills

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 at on a crisp autumn day. During a visit to Hudson-Chatham Winery, you can taste a variety of different wines from the Hudson Valley wine region.

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

Day 7: Wrap Up Your New England Fall Trip

A woman enjoying a fall road trip.

On the final day of your New England fall road trip itinerary, you can either 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 to do 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.)


A woman at Miraval in the Berkshires during her New England fall road trip itinerary

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 [email protected]

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.

Shop my New England Look:

Click here to shop my Poshmark closet!

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2 Comments

  1. Kim Deer on September 1, 2022 at 12:06 am

    This is the perfect week trip to the stunning New England area ~ that area is gorgeous to begin with but in the fall it is fabulous! Nothing like being out in nature during the fall months in New England. Great nature scenes, restaurants, hikes and many more fun filled activities! Can’t wait to visit this area again this fall ~ love you, mom xoxo ♥️👩🏻

    • Taylor Deer on September 6, 2022 at 9:32 pm

      It really was such a fun trip last year. New England truly is a gem during the fall!

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Taylor-Sleepy-Hollow-Farm3

A woman enjoying fall in Woodstock, Vermont

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 for you to follow as you plan your leaf peeping trip for this year!

A woman enjoying fall foliage at Artist Bluff in New Hampshire

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

I did my Northeast road trip with Hannah Liz Weaver and we had the time of our lives! As you are planning your New England fall foliage trip, I recommend following my 1-week itinerary that is listed below in the article.

**Please note that this blog post uses affiliate links meaning that if you make a purchase via my affiliate link, I receive a small commission at no additional cost to you. I only promote and talk about products and services that I have used and like.


Pin the Below Image to Keep Handy

New England Fall Road Trip Itinerary

Traveling around the New England States:

A woman at Sleepy Hollow Farm during a New England fall road trip itinerary

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 the city of 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. During the way, I picked Hannah up from Boston Logan since she flew from Dallas.

Fall foliage in New England

Whether you decide to 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 Northeast Road Trip:

A woman staying at The Valley Inn in New Hampshire's White Mountains during a New England fall

All throughout New England, you can find a plethora of 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.

The Best New England Fall Road Trip Itinerary:

A woman staying at Mountain Meadows Lodge in Killington, Vermont during a Vermont road trip itinerary

Day 1: Arrive in New Hampshire’s White Mountains

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

Hotels to Stay at in New Hampshire’s White Mountains:

A woman staying in Waterville Valley in New Hampshire during a New England fall road trip itinerary

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. From there, you will be hungry, so I suggest enjoying a nice lunch or dinner at Covered Bridge Farm Table. It is a cozy American restaurant that overlooks the scenic Penigewasset River and historic Blair Covered Bridge. (Both New Hampshire and Vermont are known for their iconic covered bridges.)

Flume Gorge:

Flume Gorge in New Hampshire

If you have time in on your first day, I recommend checking out Flume Gorge. It is known as one of the best jewels of Franconia Notch State Park. Flume Gorge, which was 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 beautiful fall colors of New Hampshire's White Mountains

On your second full day in New Hampshire, enjoy all the beautiful fall foliage in Franconia Notch State Park! First, I suggest enjoying a nice breakfast at Polly’s Pancake Parlor in Sugar Hill.

Artist Bluff Trail:

A woman at the top of Artist Bluff trail during a New England fall road trip in New Hampshire

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:

New Hampshire White Mountains with fall foliage

If you don’t want to hike, I recommend riding the Cannon Mountain Aerial Tramway in the State Park. 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 even Canada!

The tram runs between 9am to 5pm 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 5 and under.

For lunch, a great place to visit is Littleton Freehouse Taproom & Eatery that 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.

Kancamagus Scenic Byway:

Driving the Kancamagus Scenic Byway during a New England fall road trip itinerary

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 fall road trips in New England!

Please note that you must have a full tank of gas before you start driving on Kancamagus Highway. Once you drive past the town of Lincoln, there are no gas stations nor cell phone reception.

Along the Kancamagus fall foliage drive, you’ll admire some of the best views of the White Mountains, the 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 enjoying pizza at Matty B’s in Bartlett.

Day 3: Wander Around the Charming Fall Town of Woodstock, Vermont

A woman at Woodstock Inn & Resort in Vermont during fall

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 a little 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!

Woodstock, Vermont:

Checking out the New England town of Woodstock during a Vermont road trip itinerary in the fall

After enjoying a late breakfast at Mon Vert Café, walk over to the Woodstock Inn. This charming luxury hotel has a lot of beautiful fall décor and plants to enjoy. At Woodstock Inn, you can make a reservation at one of the four restaurants or even 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 different 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.

A woman at Sleepy Hollow Farm in Woodstock, Vermont

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 one of the most “Instagrammable” spots in Woodstock, 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 crafted 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

A woman enjoying Halloween decorations in Woodstock, Vermont during a New England fall road trip

Even though I made my way to the Berkshires on my 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.

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:

Fall foliage in Vermont

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 that has 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. There are also great waterfall hikes such as Bingham Falls and Moss Glen Falls.

Stowe, Vermont:

Cider tasting at Cold Hollow Cider Mill in Stowe, Vermont

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 country store and market, bakery, restaurant and cidery.

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

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

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

Visiting Ben & Jerry's during a New England fall road trip itinerary

Afterwards, 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 flavors!

Before you head back to Woodstock, take a fun ride on the Gondola Skyride to the summit of Mount Mansfield, which is 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 prices 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 5 years of age are free to ride the gondola with a parent or guardian.

When you arrive back in 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

A woman staying at Red Lion Inn in the Berkshires during a fall road trip

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:

A woman at the top of Monument Mountain in the Berkshires during fall

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

Pittsfield, Massachusetts:

A woman at Balderdash Cellars in the Berkshires during a New England fall road trip itinerary

For lunch, head to the town of Pittsfield to savor a delicious meal at Mission Restaurant. It is an incredible tapas and wine bar that features 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 all around.

Great Barrington, Massachusetts:

Visiting Great Barrington in the Berkshires during a New England fall road trip

In the evening, head into the town of Great Barrington to enjoy delicious food and drinks. A swanky cocktail bar with incredible small plates is Mooncloud Lounge and an awesome restaurant to eat dinner at is Agaves Mexican Grill. In general, Great Barrington is also a charming town to stroll through and enjoy awesome shopping, live music and art galleries.

Day 6: Enjoy Fall Foliage in the New York Catskills

A woman staying at a Getaway House in the Catskills of New York

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

A fall hike in the Northeast

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, it is a must to also add on Upstate New York to your itinerary. Even though New York isn’t technically New England, it is still a stunning destination to see fall colors and it’s in close driving distance to a lot of spots in Massachusetts, Vermont and Connecticut.

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

Kaatserskill Falls and Hunter Mountain:

Oktoberfest in the Northeast USA

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. During the winter, it is a ski resort, but in autumn, they host a great Oktoberfest event to enjoy amongst the fall colors.

Tannersville, New York:

Wine tasting at Hudson-Chatham Winery in the Catskills

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 at on a crisp autumn day. During a visit to Hudson-Chatham Winery, you can taste a variety of different wines from the Hudson Valley wine region.

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

Day 7: Wrap Up Your New England Fall Trip

A woman enjoying a fall road trip.

On the final day of your New England fall road trip itinerary, you can either 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 to do 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.)


A woman at Miraval in the Berkshires during her New England fall road trip itinerary

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 [email protected]

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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2 Comments

  1. Kim Deer on September 1, 2022 at 12:06 am

    This is the perfect week trip to the stunning New England area ~ that area is gorgeous to begin with but in the fall it is fabulous! Nothing like being out in nature during the fall months in New England. Great nature scenes, restaurants, hikes and many more fun filled activities! Can’t wait to visit this area again this fall ~ love you, mom xoxo ♥️👩🏻

    • Taylor Deer on September 6, 2022 at 9:32 pm

      It really was such a fun trip last year. New England truly is a gem during the fall!

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