The Ultimate New England Fall Road Trip Itinerary (6 States)

[Updated: August 4, 2024]

Planning the New England Fall Road Trip of your dreams? You’ve come to the right place! In this guide, you’ll find EVERYTHING you need to plan a bucket list Fall Road Trip through all 6 New England states.

I’ll cover the best routes to take, must-see places for fall foliage, fun activities, where to stay, what to eat, what to pack, and much, much more. Whew! That’s a lot, but I did say you’ll get everything you need to plan your dream New England Fall Road Trip.

Let me tell you, New England is a bucket list destination during the fall for a reason. My expectations were sky-high, and the reality blew me away.

I believe this is the best New England fall road trip itinerary, but feel free to tweak it to fit your travel plans.

Now, let’s get planning…

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Planning The Ultimate New England Fall Road Trip

When I say this is The Ultimate New England Fall Road Trip Itinerary, I mean IT!

My husband and I covered ALL SIX NEW ENGLAND STATES, (Massachusetts, Maine, New Hampshire, Vermont, Connecticut, and Rhode Island) in just two weeks during mid-October.

First, before we get into it, I want to mention that I experienced New England in October 2020, right in the middle of COVID. Luckily, everything was open, but figuring out accommodations was a bit tricky. But honestly the timing worked in our favor, and I gathered a lot of tips and tricks that’ll help you plan your trip.

Also, I have to mention that not every year will be the same for fall colors. This is very weather-dependent, and some years will be better than others. With that being said, I’ll do my best to help you plan an epic fall road trip.

Let’s get started…

Where to Stay on Your New England Fall Road Trip

Figuring out where your going to stay on your New England fall road trip isn’t as strait forward as you might think. Is it better to book ahead? Or should you keep it spontaneous and book on the fly? I’m going to cover your best options here:

Reservations vs Spontaneity

Most people recommend booking accommodations in advance, especially during peak fall season. However, I don’t completely agree with them.

Booking last minute allows you to follow the foliage. You don’t want to finally get your chance at a bucket list trip and miss the vivid colors just because you made reservations where the leaves have already fallen off the trees. That would be very, very sad!

We did our entire road trip without making any reservations in advance. We booked the day of, depending on where we were, how far we wanted to drive, and how tired we were.

The downside to booking on the fly is that you might pay more since the deals get snatched up quickly. But, if you’re up for an adventure, there are ways around this. Keep reading…

Camping: A Great Option

Camping is the answer to staying flexible, not worrying about accommodation reservations, and saving A LOT of money!

We discovered that camping is the absolute best way to road trip New England in the fall. By accident, not by choice. You see, when my husband and I went to New England in October of 2020, Covid was still a thing. It made traditional accommodations tricky.

So, we decided to give the car camper route a try, and it turned out to be the best experience ever!

We rented a large SUV with seats that folded flat, bought an inexpensive blow-up mattress, and brought our sleeping bags and travel pillows with us. This setup was perfect and budget-friendly.

🍁 Pro Tip: For a cozy camping experience in your car, pack a good sleeping bag, warm pajamas, and thermal socks. You’ll be snug and comfortable while surrounded by gorgeous fall foliage.

Finding Campsites

Now, it’s important to know that some campgrounds begin to close in the fall, but we didn’t have much trouble because we opted for FREE or “Wild” camping when we could!

If you want to find areas where you can camp for free, check out the BLM website and explore their interactive map or the USFS website for rules and regulations.

RV or Camper Rentals

If sleeping in your car doesn’t sound appealing, consider renting an RV or camper from Outdoorsy for more comfortable while camping.

When To Visit New England for the Best Colors?

I want to cover this topic in more detail since it is the most critical factor for planning a successful fall road trip in New England!

New England’s breathtaking sea of colors draws travelers from all over the world. To ensure you can catch the fall foliage at its most spectacular, it’s essential to time your visit just right.

New England’s peak fall foliage is somewhat unpredictable! Peak fall foliage doesn’t happen at the exact same time every year. The exact timing can vary on these factors:

• Specific location and elevation within the region.
• How much water did the trees get during the year?
• But mostly, weather conditions and temperatures in any given year.

🍁 Pro Tip: Before you hit the road, check fall foliage prediction maps closer to your travel dates to see where the colors are peaking. You can also look at online webcams for real-time images of the foliage in different areas and parks.

Fall Colors Quick Guide for New England

This quick guide breaks down the ideal times to explore each region, making sure you catch the colors at their peak. Whether you’re starting early or catching the late colors, you’ll know exactly when and where to go.

🍃 Mid-September:

If you’re schedule only allows you to visit mid-September, then I would head north for a taste of early autumn. Northern Vermont and New Hampshire will show the first signs of fall colors. The benefit of a road trip at this time is that it is quieter and less crowded.

🍁 Late September to Early October:

As late September and early October rolls in, New England’s fall colors hits its stride. The trees and hills burst into bold reds, oranges, and golds. During this time, the White Mountains of New Hampshire, the Green Mountains of Vermont, and coastal Maine showoff their most stunning colors.

This is what you would call Peak Fall Foliage Season. Plan your visit in the first week of October for the best chance of hitting peak fall colors.

🍂 Mid to Late October:

If you visit in late October, I recommend you hunt for fall colors in the lower states like Massachusetts, Connecticut, or Rhode Island. This is getting late in the season, and the colors will have moved south.

No matter when you visit, New England won’t let you down. Just pick the time that works best for you and your schedule and go where the colors are.

How Many Days for a New England Fall Trip?

How many days do you have? That’s the real question. I believe the more, the better!

My husband and I spent two weeks (14 days) exploring all six New England states, and honestly, we could have used another week.

There’s no one-size-fits-all answer, but here are some guidelines to help you determine how many days you might need:

Long Weekend (3-4 Days):

If you’re pressed for time, a long weekend in New England can still give you a taste of fall. Focus on one or two beautiful towns, or really explore a single state like Vermont. Be selective and prioritize your choices, and you will have the best New England fall mini-road trip.

Week-Long Journey (7-8 Days):

I suggest spending one week at a minimum in New England. In this amount of time, you could explore two or three states and their top attractions. It will allow you to explore a region a little deeper and have a better chance of seeing peak fall colors.

Extended Adventure (10-14 Days or More):

If you can, extend your fall road trip to 10 days or more. This will allow you to really explore New England and all it has to offer. No stone unturned, so to speak. You’ll dive deeper into each state, discover hidden gems, and take detours along the way.

Two weeks would make for the Ultimate New England Fall Road Trip.

🍁 Pro Tip: Allow extra time for driving between destinations and take the scenic routes, even if they’re slower than highways. This way, you can really soak in the charm of New England.

Some Things You Should Know About This Itinerary

Starts in Boston:

Our adventure began in the fun city of Boston, where we flew into Logan International Airport. Boston is an excellent launching point for a New England Road Trip, with lots of awesome things to do, delicious seafood, and cobblestone streets.

A Counterclockwise Road Trip:

This fall road trip follows a counterclockwise route, covering all six New England states—Massachusetts, Maine, New Hampshire, Vermont, Connecticut, and Rhode Island.

Starting in Boston, Massachusetts, you’ll make your way north along the coast to Bar Harbor Maine. Crossing over from there to Vermont and zig zagging your way back down, hitting all the best sites in Vermont, Connecticut, and Rhode Island. You’ll explore historic cities, beautiful coastal towns, and mountainous regions.

True Road Trip Style:

This 14-day itinerary is designed in true road trip fashion, which means there’s quite a bit of driving involved, and most stays are for just one night. This allows you to cover a lot of ground and experience all of New England’s amazing fall destinations.

Of course, I know everyone has their own style and pace when it comes to traveling. So, feel free to change this itinerary to your liking.

🍁 Pro Tip: Customize your New England road trip based on the things that excite you. Like, If you love hiking, plan extra days in the White Mountains of New Hampshire or if your obsessed with covered bridges, like I am, then Vermont is where its at. Just make the trip truly your own.

New England Fall Road Trip At a Glance

Here’s a quick overview of your ultimate New England fall road trip.

Day 1: Arrival in Boston, Massachusetts

Day 2: Explore the city of Boston

Days 3-5: Explore Maine’s Coast Line & Acadia National Park

Day 6: Drive to Jackson, New Hampshire

Days 7: Drive the Kancamagus Highway and head up to Montgomery, VT

Days 8-9: Explore Stowe, Woodstock & Green Mountains, Vermont

Day 10: Explore the Berkshires, Massachusetts

Day 11: Litchfield Hills & Essex Connecticut

Day 12: Newport, Rhode Island

Day 13: Back to Boston for one Night

Day 14: Fly Home

The Ultimate New England Fall Road Trip Itinerary

Buckle up and get ready to chase those fall colors! Here’s the ultimate fall road trip itinerary through all six New England states.

Day 1 – Arrive in Boston

Depending on what time of day you arrive, take today to get settled into your hotel, maybe take in a few sites around the city, and grab a delicious seafood dinner down by the marina.

Here is what we did for reference:

• Grabbed an Uber to our hotel from the airport.
• We stayed at the Club Quarters Hotel for our first two nights in Boston. (We chose this hotel for its good location and walking distance to all the highlights.)
• After we settled into our room, we were starving! We walked down to the Marina in search of a seafood dinner. We chose to eat at the Chart House on Long Wharf. (Great atmosphere and amazing seafood! Highly recommend.)
• After dinner, we decided to do a little pre-road trip celebration with a self-guided pub crawl. Some of our favorites we popped into were, The Black Rose, The Broadside Tavern, Emmets, and Mr Dooley’s.

🍁 FYI: We chose to kick off our New England road trip with TWO NIGHTS in Boston. If you want to take in the historical city of Boston as we did, then you can either start your trip with Boston or tack it on at the end.

Day 2 – Explore The City of Boston

Today you will explore Boston on foot. I found Boston to be a very walkable city with quaint streets and hidden gems around every corner.

The best way to see all the top sites in Boston is by following the Freedom Trail.

You can start your self-guided Freedom Trail tour by picking up your guide book at the visitors center Boston Commons, located at 139 Tremont Street. You’ll finish the trail at the USS Constitution Battleship Museum.

Along the way, you’ll see all the famous sites and plenty of hidden gems. Don’t hesitate to take detours and enjoy the freedom of wandering!

🍁 FYI: Fall foliage peaks later in Boston—usually mid to late October. We did not see any fall foliage in the City of Boston until we came back around on our way home.

Freedom Trail Highlights

We were able to accomplish everything on the list below in one day.

• Freedom Trail: Walk along this 2.5-mile-long trail that takes you through 16 historical sites, including the Massachusetts State House, Old North Church, and Paul Revere’s House.
• Boston Common and Public Garden: Stroll through the oldest public park in the United States, Boston Common, and its adjacent Public Garden, known for its swan boats.
• Quincy Market and Faneuil Hall: Shop, dine, and enjoy street performances at Quincy Market, and learn about Boston’s history at Faneuil Hall.
• USS Constitution Museum: Explore “Old Ironsides,” the nickname for the world’s oldest commissioned warship still afloat, and learn about its history in the adjacent museum.
• Beacon Hill: Wander through the picturesque streets of Beacon Hill, known for its historic brick townhouses, gas street lamps, and charming ambiance.
• Union Oyster House: Eat at one of the oldest continuously operating restaurants in the United States. Order up some oysters or try their famous clam chowder.

More Things to do in Boston

We did not do these, but I wanted to give you other popular options so you could tailor your visit to your liking.

• Hop-On Hop-Off Trolley Tour: These are a fantastic way to see the city sites without having to walk everywhere.
• Fenway Park: If you’re a baseball fan, catch a game at the iconic Fenway Park, home to the Boston Red Sox, or take a guided tour of the stadium.
• Food Tour: Boston has a rich food culture! Book a guided food tour, if your schedule allows, that takes you to all the best places to eat.
• Duck Boat Sightseeing City Tour: Jump on a Duck Boat for a fun and unique tour of Boston by land and water. You’ll see the city’s top spots.

For more of Boston’s top tours and activities, check out Viator or Get Your Guide.

Day 3-5: Explore Maine’s Coastline

It’s time to hit the road my friend! How excited are you?

First, you’re going to need some wheels. Pick up your rental car early and start making your way up the coastline.

🍁 FYI: We loved Maine! Initially, we planned on only spending two nights in Maine, but because we weren’t ready to leave, we added a third night. The benefit of not having a hotel or campsite reservation in advance, is we have the freedom and flexibility to adjust our trip!

Day 3: Salem & York, Maine

On your way up the coastline, consider making a pit stop to check out the witchy town of Salem, Massachusetts. This is an incredibly popular town known for the 1692 witch trials!

Salem is just an hour dive North of Boston.

🍁 FYI: The town is VERY crowded and the parking is atrocious! We drove around for nearly an hour looking for a parking spot. Although it was a cute witchy town, the crowds kinda ruined it for us.

Tips to make your Salem visit more enjoyable:

• I highly suggest parking outside of town and then grabbing an Uber or taxi that can drop you off in the town of Salem. If I had known we would have spent 45 minutes driving around looking for parking, we would have just skipped over Salem.
• Another great idea is to do a day trip from Boston to Salem via the Ferry.

MOVING ON!

Make your way up North along the coastline of Maine.

This drive is absolutely beautiful! There are plenty of stops along the coastline where you will want to get out and take pictures.

Stop in a charming seaside town like Newburyport, Massachusetts, for lunch, shopping, and to sample my favorite seasonal treat – PUMPKIN BEER!

Stop for the Night in YORK, MAINE.

York, Maine will be a 1 hour drive north of Salem, Massachusetts.

🍁 FYI: Because there were no options for free camping in this area, we camped at York Beach Camper Park, just outside of town. It wasn’t a free campsite, but it was very affordable and a short 7-minute walk to the town center. Provided us with a great location for exploring the cute coastal town of York.

Things to do in York, Maine:

York, Maine, is a good stopping point. It is a stunning coastal town with lots of historical charm. Below is the list of things we did during our time in York.

• Dip your toes in the Atlantic Ocean along Short Sands Beach (one of the nicest beaches in Maine).
• Stroll through the boutique shops in York Village, where you can grab yourself a unique handmade souvenir.
• Grab dinner with a view from the restaurant at Union Bluff Hotel. (I had the best Lobster Roll of the entire trip here!)
• Watch the Sunrise from Nubble Lighthouse in the morning. You won’t regret waking up early for this!
• Another must-do before you leave town is to grab a home-cooked style breakfast from The Goldenrod!

Day 4: Lighthouses & Portland, Maine

Along your drive up the coastline, the farther North you go, the better the fall colors get.

Be sure to stop at some of the beautiful lighthouses Maine is known for. Portland Head Light Lighthouse and Marshall Point Lighthouse were two of my favorites. You may recognize the Marshall Point lighthouse from the movie Forest Gump.

The Portland Head Light is one of the most photographed lighthouses in the United States.

Make a day stop in PORTLAND, MAINE. – 45 minute drive from York.

Below you will find a list of our favorite things we did in Portland.

List of things to do in Portland, Maine:

• Explore the charming Old Port district with its cobblestone streets, historic architecture, and boutique shops. It’s a great place for a leisurely stroll, shopping, and people-watching.
• Walk along the working waterfront or take a harbor cruise.
• Don’t miss the chance to eat fresh Maine lobster, lobster rolls, and clam chowder at one of the many restaurants, seafood shacks and food markets.
• Ship home fresh whole lobsters from a Fish Market!

🍁 FYI: We shipped my parents four fresh lobsters for their Anniversary from Harbor Fish Market. It was the cheapest lobster I’ve ever bought. And my parents were so excited when they arrived the next day alive!! They said it was the best lobster they had ever eaten.

🍁 FYI: We camped this night at Oceanfront Camping at Reach Knolls. It was the perfect location with beautiful views of the ocean and surrounded by fall foliage. We had our morning coffees on a bench overlooking the ocean!

The drive to Oceanfront Camping at Reach Knolls takes 3 hours to reach without stops from Portland, Maine. Of course, we stopped a lot, so it was dark when we pulled in for the night.

Day 5: Stonington, Bar Harbor & Acadia National Park, Maine

Drive 30 minutes down to the cute working waterfront town of STONINGTON, ME.

Located on Deer Isle, Stonington is a charming lobster port. In fact, it is the most popular and largest lobster port in Maine.

• You will find cute houses of all different colors, lobster boats, seafood shacks, and fishermen going about their daily chores. You will get an authentic glimpse into Maine’s coastal way of life.
• Consider taking a lobster boat tour to learn about the lobstering. You’ll also have the chance to see the beauty of the Maine coastline from the water.

🍁 FYI: We ate our favorite lobster meal in Stonington! I had homemade lobster stew, and my husband had a lobster patty melt that was to die for! My mouth is watering just thinking about it.

Next stop, ACADIA NATIONAL PARK! It is one of the most beautiful and popular national parks in the United States. Bar Harbor, Maine, is the gateway to Acadia National Park.

Try to arrive early and head straight into the park. The drive takes 1 hour 20 minutes with out stopping from Stonington.

The best things to do in Acadia National Park:

• Go for a hike on one of the park’s hiking trails. Some popular hiking trails include Jordan Pond Path, Precipice Trail, and Cadillac Mountain South Ridge Trail.
• Take a scenic drive along the Park Loop Road, which offers some of the most scenic views with fall foliage in New England.
• Rent a bicycle and explore the Carriage Roads, a network of car-free paths designed by John D. Rockefeller Jr., offering picturesque routes.
• Make sure you drive to the summit of Cadillac Mountain in the morning to witness the first sunrise in the U.S. Also, you will get stunning panoramic views at any time of the day!

After exploring Acadia National Park, it’s probably time for you to check into your hotel or camping spot.

Bar Harbor, located just outside the park is where most travelers choose to stay when visiting the park.

Get settled, then head out to explore the town of BAR HARBOR.

🍁 FYI: We decided to get a hotel room this night in Bar Harbor at the Holiday Inn Resort Bar Harbor. I had caught a chill, out hiking in Acadia National Park, that I just couldn’t shake. So we found a room last minute that had a HOT TUB so I could get rid of my chill!

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List of the best things to do in Bar Harbor, Maine:

• Stroll through the charming and walkable downtown area of Bar Harbor. Here, you’ll find boutique shops, art galleries, cafes, and souvenir stores.
• Eat fresh Maine lobster and seafood at local restaurants and lobster pounds, such as Thurston’s Lobster Pound.
• Walk along the Bar Harbor shore path. This picturesque path hugs the shoreline and provides beautiful views of the harbor.
• Eat Lobster ice cream! Yes, you can even eat lobster in ice cream and it’s not bad.
• Take a scenic schooner cruise around Frenchman Bay to enjoy breathtaking views and the sunset.

🍁 Pro Tip: Visit Acadia National Park during less crowded times of the day. While sunrise at Cadillac Mountain is popular, you can enjoy the views by going later in the morning or early afternoon. It’ll be a much quieter experience if you visit the park during off-peak hours.

Day 6: Drive to Jackson, New Hampshire

Today is a long day of driving!

After you wake up early and catch the sunrise on top of Cadillac Mountain in Acadia National Park, you will then make your way across Maine to Jackson, New Hampshire.

Without stops, this drive will take you about 4.5 hours.

Stops I recommend making along the way:

• Lovejoy Covered Bridge
• Sunday River Bridge

These covered bridges are a little off the main route. I was so excited to get to see my first covered bridges that we made the detour just for them. They were very much worth it, in my opinion!

🍁 FYI: I’m obsessed with covered bridges, so you’ll see a lot of them here! Don’t worry, I’ll also share plenty of other fascinating things to see in New England. You won’t be stuck just looking at bridges!

Spend the Night in JACKSON, NEW HAMPSHIRE.

Jackson is a good starting point for the must-drive Kancamagus Highway that we will be driving tomorrow!

Here are fun things to do in Jackson, NH:

• If you arrive early enough, I highly suggest you take a drive about 45 minutes outside of Jackson and ride The Mount Washington Cog Railway! This is the world’s first mountain-climbing cog railway and it takes you to the top of the tallest peak in New England – Mount Washington! This is one of the best fall experiences in New England!
• Also, on your way to the Cog railway, you will drive through Crawford Notch State Park, which is a beautiful dive for leaf peeping.
• Take a walk down along Jackson Falls in the center of the village.

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🍁 FYI: We found a sweet little spot in the White Mountain National Forest just outside of Jackson to free camp that night. There are no amenities, but it’s FREE!

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Day 7: Drive The Kancamagus Highway, then up to Montgomery, Vermont

Start your day early because we have a lot of beautiful things to see and ground to cover today!

Driving the KANCAMAGUS HIGHWAY, also known as the “The Knac” is an absolute must on your New England fall road trip! This route is known to have some of the best fall foliage in the country and takes you right through the heart of the White Mountains in New Hampshire.

You can get on The Knac at Conway, which is 23 minutes outside of Jackson.

But, before you hop on the scenic highway, stop at the Eliss River Covered Bridge and The Honeymoon Covered Bridge in North Conway.

Kancamagus Highway Tips:

• Once you are on The Knac there are no bathrooms, no gas stations, no restaurants, and no other businesses, so plan accordingly!
• There is no cell service either, so it would be a good idea to make sure your maps are downloaded onto your phone before you lose service.
• The drive is 35.5 miles long and takes 45 minutes to drive one way, but you will want to budget for about 2 hours, allowing you plenty of time to enjoy the breathtaking view of fall foliage from the lookouts.
• The Knac offers 6 campgrounds for those who want to spend more time exploring the White Mountains.

Places to visit along The Knac:

• Swift River Covered Bridge
• Albany Covered Bridge
• Rocky Gorge – picturesque viewpoints where you can see the swift river rush through a narrow gorge.
• Sabbaday Falls – a short hike leads to these beautiful falls
• Scenic Overlooks: Sugar Hill Overlook, Pemi Overlook, and the Hancock Overlook.
• Lincoln Woods Trailhead – Scenic suspension bridge.

🍁 Pro Tip: Before you hop on The Knac, download an audio tour to enhance your drive along this iconic scenic highway. We downloaded this audio tour, which really added to our road trip experience! We recommend it!

The next stop is the FRANCONIA NOTCH STATE PARK.

• The FLUME GORGE is one thing within the Franconia Notch State Park that I highly recommend you add to your itinerary! It is an easy 2-mile loop that takes you through a granite gorge with waterfalls and beautiful fall colors and crosses two covered bridges.
• Be sure to buy your tickets online to save a few bucks and reserve your time slot for entry. We bought our tickets online when we got to the parking lot. We only had to wait about 20 minutes for our time slot.

Okay – at this point, you have two options. (Well, actually, the options are endless, but I’m only giving you two!)

Option 1:

You can continue North, cross into Vermont, and head to Montgomery, Vermont. Why Montgomery, you may ask? Well, because it is the covered bridge capital!

At one time, the town had 13 covered bridges. Currently, Montgomery has six beautiful covered Bridges inside the town and one more on the border.

The drive will take 1 hour and 40 minutes without stopping to reach Montgomery from Franconia Notch State Park.

Option 2:

If you’re rolling your eyes and don’t want to drive through some of the most beautiful countryside, with rolling hills and fall foliage I’ve ever seen, to see a bunch of covered bridges, then I suggest you head to Stowe, VT.

If you choose to head to Stowe, VT instead, the drive will take 1 hour and 30 minutes without stopping.

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🍁 FYI: Montgomery is the start of the famous Highway 100 that runs the full length of Vermont and has been said to be the most scenic route in the state, especially in the Fall. I completely agree!! It’s a leaf-peeping paradise!

For dinner grab a homemade pizza at the pub in Montgomery and camp on the outskirts of town for FREE!

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Days 8-10: Explore Stowe, Woodstock & Green Mountains, Vermont

Vermont was my favorite New England State, and we ended up spending three days exploring it. But honestly, we could have stayed longer!

Day 8: Drive to Stowe, Vermont

In the morning, get up early, grab a coffee, and hit the back country roads in search of charming towns and fall foliage. Some of the best hidden gems await to be uncovered as you make your way down Highway 100 to Stowe, VT.

The drive will take 50 minutes without stopping to reach Stowe from Montgomery. That’s if you don’t take the back country roads.

I highly recommend you take the back roads!!

Places to visit along the way to Stowe:

• Vermont is known for its covered bridges, and you’ll pass several along Highway 100. Notable ones include the Hutchins Covered Bridge in Montgomery and the Grist Mill Covered Bridge in Jeffersonville.
• A detour to Smugglers’ Notch State Park is worth your while for its stunning mountain scenery, hiking trails, and opportunities for leaf peeping.
• Ride the gondola to the top of Mount Mansfield. This is the highest peak in Vermont.
• Head up the mountain to the Von Trapp Brewing Bierhall. Raise a glass to fall with craft beer and delicious Austrian food. We tried our first schnitzel here, and it was so freaking good!

Best things to do in Stowe:

• Explore the cute shops on Main street. Be sure to pop in the Stowe Mercantile.
• Walk or bike the Stowe Recreation Path that starts behind the Stowe Community Church and runs 5.3-mile along the river.
• Photograph the towns beautiful white church – the most photographed church in the United States.
• Stop at sugar shacks along the way and sample maple syrup goodies.
• Visit Cold Hollow Cider Mill and try freshly pressed apple cider, cider donuts, and other seasonal delights such as a flute of hard ciders.
• Tour the famous Ben & Jerry’s ice cream factory and sample seasonal flavors of ice cream.

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🍁 FYI: About 40 minutes south of Stowe, VT, we found a strip of national forest where we wild camped for the night. We were not the only ones camping here, but it was a safe and beautiful location to have a FREE campsite for the night. We got a bundle of firewood from a store in Waitsfield and had a cozy fire to sit around and watch the stars come out.

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Day 9: Drive to Woodstock

Today, you will explore pumpkin patches, farm stands, sugar shacks, apple orchards, more covered bridges, and farms decked out in fall foliage all along the scenic Highway 100.

The best part of this whole road trip is this route, in my opinion!

The drive from Stowe to Woodstock will take 1 hour and 20 minutes without stopping.

When you reach Woodstock, you will feel like you stepped into a storybook. It’s a very charming town that has historic brick buildings, covered bridges, a general store, and white churches and is surrounded by beautiful farming country.

Places to stop along the way to Woodstock:

• You will come across farm stands selling fresh produce, cheese, and other local goods. My favorite part was their honor pay system!
• There are several cute pumpkin patches to stop at along the way. You can dream of picking the perfect pumpkin for carving if you weren’t on a road trip.
• Apple orchards are another fun seasonal stop where you can pick some yummy apples for the road.
• More covered bridges – of course!

Best things to do in Woodstock:

• Snap some pictures of the famous farm landscape of Sleepy Hollow Farm.
• Take a tour of Sugarbush Farm and sample homemade cheese and fresh maple syrup and also see amazing fall foliage views.
• A Scenic drive down Cloudland Road
• Quechee Gorge overlook – Known as Vermont’s “Little Grand Canyon,”
• Hike in Marsh Billings Rockefeller Park to an amazing viewpoint overlooking Woodstock
• Visit Billings Farm and Museum, a working dairy farm, and see Jersey dairy cows
• Explore the historic covered bridges – Middle Bridge & Taftsville Covered Bridge
• Explore nearby Quechee Gorge and its village.
• Stroll through the charming downtown boutique shops, galleries, and quaint cafes.
• Eat at a farm-to-table restaurant to taste locally grown food and produce. We had an incredible meal at Worthy Kitchen!
• Stop by to see the Cornish Windsor Covered Bridge, just a short drive away. It’s the longest wooden bridge in the U.S. and the longest two-span covered bridge in the world!

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🍁 FYI: We did not stay the night in Woodstock. We ventured down the road a little further to a town called Lebanon on the Vermont/New Hampshire border. We chose to stay in a hotel this night for a hot shower! This town had more affordable accommodations than Woodstock, had a grocery store, and also put us right next to the the famous Cornish Windsor Covered Bridge that I wanted to see the next day!

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Day 10: Explore Berkshires, Massachusetts

The Berkshires in the western region of Massachusetts have the most beautiful fall foliage in the State. You’ll find beautiful landscapes full of vivid fall colors, rustic cabins, and charming towns throughout.

As you leave Woodstock, you can expect to drive 2 hours without stops to reach the Berkshires.

But be sure to make a pit stop at a little town called Rockingham, VT, and pop into the Vermont County Store and also snap a picture at the Kissing Covered Bridge

Things to see in the Berkshires:

• Explore the Mount Greylock area. Mount Greylock is the highest peak in Massachusetts and is covered in fall foliage during the season.
• Walk or bike the Ashuwillticook Rail Trail in Lanesborough. This trail is 11 miles of some of the prettiest fall colors.
• Visit the Bartlett’s Orchard & Hilltop Orchards and sample some hard ciders and craft beers.
• Stroll through the adorable towns of Lenox and Stockbridge!
• Swing by and see another pretty covered bridge in Sheffield.

After spending the day exploring the Berkshires, head down to Litchfield, CT, for the Night.

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🍁 FYI: We ran out of national forest camping options after Vermont, so we stayed at the Hopkins Inn in Litchfield, CT. It’s a cozy inn with great views of Lake Waramaug and was affordable. Highly recommend!

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Day 11: Litchfield Hills & Essex, Connecticut

Today, You can Explore the Litchfield area of Connecticut. Kent and Warren are charming towns in the area worth exploring. You should have followed the fall foliage as it moved down, so it should be blazing in Connecticut by now.

Continue on your way to the town of ESSEX, CONNECTICUT, a historic seaport village. The drive from Litchfield to Essex will take you 1 hour and 20 minutes without stops.

Things to Do in Essex, Connecticut:

• Take a fall foliage train ride on the historical Essex Steam Train, aka The Valley Railroad Company. This train ride is an hour long and takes you up the Connecticut River valley into beautiful fall colors. (My husband is a fanatic when it comes to steam trains. He’s like I am with covered bridges! I had to surprise him with a ride on this beautiful steam train in its historic passenger rail cars. My husband was like a kid in a candy store! )
• Visit some local wineries and tour their vineyards. We enjoyed sampling wine and exploring the vines at Sunset Hill Vineyard.
• Stroll through the quaint Essex Village center with its historic buildings, boutique shops, and galleries.
• Spend a night at The Griswold Inn, which is one of the oldest continuously operated hotels in the US. It was built in 1776 and beautifully restored to represent the charm of that era. Located in the Historic seaport of Essex, it is a must when choosing a place to stay for the night. (We chose to stay here this night and loved our time there. Be sure to check out their cool old bar and eat a delicious dinner in their restaurant.)

Day 12: Newport, Rhode Island

If you haven’t run out of time on your New England Fall Road Trip, you should try to make it to the charming town of Newport, RI.

This coastal town was such a gem, and we wished we had one more day to explore it more!

The drive from Essex, CT, to Newport, RI, will take you 1 hour 20 minutes with no stops.

Best things to do in Newport, Rhode Island:

• Take a scenic walk along the cliffs that offer beautiful views of the Atlantic Ocean on one side and views of Newport’s mansions on the other.
• Tour historic mansions like The Breakers, Marble House, The Elms, Rosecliff, and Chateau-sur-Mer to step back in time and appreciate the Gilded Age architecture and lifestyle.
• Wander through Newport’s historic districts like the Point, where you’ll find well-preserved colonial-era homes and cobblestone streets.
• Stroll along the waterfront, watch boats and yachts, and enjoy al fresco dining at restaurants with ocean views.
• Relax on Newport’s beautiful beaches, including Easton’s Beach (First Beach) and Sachuest Beach (Second Beach).
• Newport is a sailing mecca, so you should consider taking a boat tour or charter to experience the city’s maritime heritage.
• Take a scenic drive along Ocean Drive, offering gorgeous coastal views and access to scenic overlooks.

Day 13: Back to Boston

Congratulations, you made it to all six New England states!!

Today is the home stretch back to Boston, Massachusetts. Are you ready to be done or sad that your road trip is coming to an end? Two weeks is a long time to be in a car, but if you followed this Itinerary, then I know you had a fantastic time!

Your drive back to Boston will take you about 2 hours. Remember to top off your rental car before you return it!

Spend your last night in Boston seeing the things you didn’t get to see when you arrived. Or if you decided to tack sightseeing in Boston onto the end of your road trip, scroll all the way back to days one and two of the itinerary for the list of must-sees and do ‘s of Boston.

🍁 FYI: We spent our last night in Boston enjoying lobster at the Boston Marina and strolling through The North End. We celebrated our Fall New England Road Trip with a pint at Mr. Dooley’s before relaxing in our hotel room. We stayed at Club Quarters Hotel, the same place we stayed when we arrived.

Day 14: Fly Home

After an amazing road trip through all six New England states, it’s time to go home. Have a safe flight home!

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What to Pack for a New England Fall Road Trip

I found New England’s weather to be finicky!

I experienced every type of fall weather in one day and sometimes all in one hour. It would be cool and crisp one minute, then the sun would come out and it would be warm, but before you know it, it’s dumping rain and freezing! Plus, the weather can vary a lot from one region to the next.

I suggest that you check the weather the week before your trip and then again the day before you leave. This way, you can make any necessary changes to your fall packing list if need be.

As a general rule, plan to pack for cooler, rainy weather, but also pack layers you can shed when the sun decides to come out.

New England Fall Packing List:

Here’s everything you need to stay comfortable and prepared on your New England fall road trip.

Layers:

• Pack long-sleeved shirts and sweaters that can be layered and shed for varying temperatures throughout the day.
• Lightweight, moisture-wicking base layers that will help you stay warm.
• New England’s weather can be unpredictable, so wear a waterproof jacket and be prepared for rain or cooler temperatures.
• A versatile fleece or down jacket. This provides extra warmth when needed.
• Keep your hands, head, and neck warm by packing a scarf, gloves, and a beanie.

Comfortable Footwear:

• Waterproof hiking boots or sturdy walking shoes.
• Comfortable shoes for everyday walking.

Casual Clothing:

• Jeans or comfortable pants. New England is pretty casual and jeans or leggings will work just fine.
• T-shirts and casual tops. Pack a mix of short and long sleeves for layering.
• Don’t forget extra pairs of hiking socks that are comfortable and breathable.

Outdoor Gear:

• Daypack or backpack for your hikes and outings.
• Portable umbrella that is windproof!.

Tech and Accessories:

• Compact Camera or smartphone to capture the stunning fall foliage and memories.
• Chargers and power banks for your devices.
• GPS or maps for navigation, especially in more remote areas with limited cell service.
• Headlamp or flashlight if you plan on camping or sunset hikes.

Personal Items:

• Pack your ID, driver’s license, insurance, and road trip itinerary, especially if you plan to rent a car.
• Carry some cash for places that do not accept cards.

Miscellaneous Items:

• Filter water bottle, especially if you plan to go on any hikes.
• Travel pillow and blanket for added comfort during long drives or overnight stays.
• Travel-sized laundry detergent for washing clothes during extended trips.

Fall Essentials:

• Pack hand warmers. These can be a lifesaver on particularly chilly days.
• Travel coffee or tea thermos. Perfect for warming up with a hot beverage on the road.

Frequently Asked Questions

Which states have the most beautiful fall foliage?

With out a doubt, Vermont and New Hampshire take the crown for fall foliage. Vermont’s Green Mountains and New Hampshire’s White Mountains are absolute must-sees for the most stunning autumn colors.

What are the must-try foods in New England during the fall?

Don’t miss the chance to try clam chowder, lobster rolls, apple cider, cider donuts, and maple syrup.

What is the best driving route to see fall foliage in New England?

The “Knac,” or the Kancamagus Highway in New Hampshire, was hands down the best route we took for fall foliage. It takes you through the White Mountains and has incredible lookouts along the way to see gorgeous fall colors as far as the eye can see. It’s a must-see on your New England road trip!

What is the best time to visit New England for the fall?

The best time to visit New England for fall foliage is from late September to mid-October. For peak colors, aim for the first week of October.

What’s the weather like during the fall in New England?

Fall weather in New England can be quite finicky. Expect cool mornings and evenings with daytime temperatures ranging from warm to moderately cool. Be prepared for rain, especially in coastal areas.

Are there any fall festivals or events in New England?

Yes, many towns and communities host fall festivals and events, celebrating the season with live music, local crafts, and traditional foods. Check local event calendars for activities during your visit.

How can I make the most of my fall road trip to New England?

Plan your trip around what you love, whether it’s hiking, wandering cute towns, or trying new foods. But be sure to leave some room for spontaneity! The best adventures often come from unexpected discoveries along the way.

That’s a Wrap: The Ultimate New England Fall Road Trip

Well, that’s a wrap!

I hope this Itinerary helps you plan your epic New England fall road trip.

Remember, this Itinerary is a guide and can be added to or rearranged to fit your schedule. With some flexibility, you will be sure to have an amazing fall road trip no matter what the weather decides to do.

Have an amazing trip!

Talk to you later