The Ultimate New England Fall Road Trip Itinerary (6 States)
I had dreamed of taking an epic fall road trip in New England for years before finally making it a reality! I can see why New England is world-famous for its fall foliage! I had high expectations, and it exceeded all my expectations and then some. If you are considering taking your own New England Fall road trip- DO IT!
I am beyond excited to share the magic of Fall in New England with you! I hope this post helps you plan your perfect New England fall road trip, too.
In this post, I will cover the route we took, the must-see places for fall foliage, must-do activities, where to stay, what to eat, what to pack, and much, much more.
I believe this is the best New England fall road trip itinerary based on real experience!
The Ultimate New England Fall Road Trip
When I say this is The Ultimate New England Fall Road Trip Itinerary, I mean this is THE ULTIMATE Fall Road Trip Itinerary!!!
My husband and I covered ALL SIX NEW ENGLAND STATES! (Massachusetts, Maine, New Hampshire, Vermont, Connecticut, and Rhode Island) We covered it all in two weeks in mid-October.
First, before we hop into it, I want to mention that my New England fall season experience was just that -“my experience.” Moreover, I experienced New England in October 2020- During COVID-19.
Luckily, everything was open, but our accommodations were a bit tricky to figure out. Ultimately, I think going during this time really worked in our favor. I gained a lot of helpful tips I feel will help you when planning your New England road trip.
Also, I have to mention that not every year will be the same for fall foliage. This is very weather-dependent, and some years will be better than others. With that being said, I will surely do my best to help you plan your epic fall road trip itinerary in New England.
It’s time to hit the road and experience THE ULTIMATE New England fall road trip!
Tips for Planning a Fall Road Trip in New England
Quick Guide: New England Fall Road Trip Planning 101.
- Choose the Right Timing! Late September to mid-October historically is the window for peak fall foliage in New England. If you shoot for the first week in October, you’ll most likely capture the best colors. (This will be discussed more below.)
- Route Planning I would start in a major city like Boston as we did. If you are flying in, they have better prices on flights. Then head north through coastal Maine, cross over through New Hampshire’s White Mountains, and Vermont’s Green Mountain national forest where you will have the best New England fall experiences. Then chase the fall foliage down through Massachusetts Berkshire Hills, Connecticut’s Litchfield hills, and finish with the scenic Rhode Island.
- States With the Best Foliage Vermont and New Hampshire have the best fall foliage, in my opinion.
- How Many Days? I’d say a minimum of seven days, but 10-14 days is ideal for your fall road trip itinerary. (This will also be discussed more below.)
- Do you need a Rental Car? You 100%, without a doubt, need a car. It’s a road trip, after all. You either live within driving distance of New England and can use your own (lucky duck!), or you’ll need to rent a car. My go-to for renting a car is Expedia or KAYAK so that you can compare prices.
- Should You Make Accommodation Reservations in Advance? The popular recommendation you’ll find is YES! Especially during the peak fall season when accommodations fill up fast. However, with that being said, I don’t completely agree with that recommendation. I feel it takes the spontaneity out of the road trip and hinders your freedom to change your route depending on where the colors are best. You don’t want to finally get your chance at a bucket list New England fall road trip and miss the vivid colors all because you made reservations where the leaves have already faded or fallen off.
FYI: We did our entire road trip without any reservations. We made ours the day of depending on where we were, how far we wanted to drive, and how tired we were. The downside to not making reservations in advance is that you might have to pay more since the deals get snatched up quickly. But, there are ways around this, especially if you are up for an adventure! (I will discuss this option below.)
Pro Tip:
Leave Room for Spontaneity!
I know it’s tempting to plan out every detail to not waste a moment of your time or money. Believe me, I know! I am a detailed trip-planning freak myself! But over time I have learned that some of the best discoveries happen when you least expect them. In this case, a New England Fall Road Trip is the best time to let go and practice flexibility in your itinerary and allow for unexpected detours. You won’t regret it!
Check out this post here if you want more fall bucket list ideas. I’ve lined up THE ULTIMATE FALL TRAVEL BUCKET LIST experiences for you!!
Camping is Another Option – or is it the BEST OPTION?
Shout out to all my fellow campers out there. I see you!
I have the answer on how to stay flexible, not worry about accommodation reservations, and save a lot of money! – CAMPING!
I 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. Many accommodations wouldn’t let out of staters stay, or you needed a negative covid test within 72 hours of your reservation.
We decided to give this whole road trip car camping thing a try. It turned out to be the best experience ever!
We rented a large SUV with seats that laid down flat in the back, went to the good ol’ Walmart, and bought a cheap blow-up full-size mattress that fit the back of the SUV. We had brought our own sleeping bags on the plane with us and travel pillows. We had our accommodation on wheels – It was perfect and cheap!
Now, it’s important to note that some campgrounds are beginning to close this time of year. We really didn’t have much difficulty with this because we chose to camp in places that were FREE or what’s called “dispersed camping.” We preferred to camp on BLM or United States Forest Service lands where we could.
If you want to find areas where you can disperse camp, then click on this BLM website and explore their interactive map or this USFS website for rules and regulations.
If you are not thrilled with the idea of sleeping in your car, then consider renting an RV or camper from Outdoorsy.
Pro Tip:
To have a cozy and comfortable camping experience sleeping in your car, make sure you pack a high-quality sleeping bag and warm pajamas. Oh, and don’t forget thermal socks, a warm hat, and gloves! Layer your clothing to stay warm during the chilly fall nights. You can be snug as a bug with the right gear and sleep comfortably in your car. All while being surrounded by the gorgeous fall foliage.
When Should You Plan 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 foliage road trip in New England!
New England’s breathtaking sea of colors draws travelers from all over the world. To ensure you catch the fall foliage at its most spectacular, it’s essential to time your visit just right.
New England’s 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.
Make sure to check the fall foliage prediction maps closer to your road trip. Or look at online webcams that give you real-time images of the fall foliage in certain areas and parks. Here is a great fall foliage map. We found it to be the most accurate.
Here is a general breakdown of when to plan your visit:
1. 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 begin to show the first signs of fall colors. The leaves are just starting to change from green to yellow and orange. The benefit of a road trip at this time is that it is quieter and less crowded.
2. Late September to Early October:
As you move deeper into September and early October, the fall foliage in New England intensifies. This is when the trees and rolling hills start to burst into vibrant shades of red, orange, and gold. The White Mountains of New Hampshire, the Green Mountains of Vermont, and the coastal areas of Maine all come alive with the most stunning colors during this time. 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.
3. Mid to Late October:
If you decide to visit this time of season, I recommend you hunt for fall foliage in the lower states like Massachusetts, Connecticut, or Rhode Island. This is getting late in the season, and the fall foliage will have moved down. Towards the end of October, the foliage may begin to fade, but there’s still beauty to be found with the leaves on the ground. It’s also a great time if you are looking to avoid larger crowds while still enjoying fall on the East Coast.
Ultimately, no matter when you plan your visit, New England won’t disappoint. Each stage of the season offers its own unique beauty. Pick the timeframe that suits you and your schedule.
How Many Days Do You Need?
How many days do you have at your disposal? 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 for an enjoyable yet all-inclusive trip:
Long Weekend (3-4 Days):
If you’re short on time, you can still experience New England in the fall with a long weekend getaway. Focus on one or two key destinations, or explore a specific state like Vermont for a taste of the autumn colors. This shorter trip allows for a bite-size portion of the fall foliage and one or two key experiences. 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 would suggest, at a minimum, spending one week in New England. A week-long trip is great if you are looking to cover a bit more ground. You could explore two or three states and their top attractions in this amount of time. It would allow you to explore a region a little deeper and see peak fall colors.
Extended Adventure (10-14 Days or More):
If you can, consider extending your fall road trip out to 10 days or more. This allows you to really explore New England and all it has to offer. No stone unturned, so to speak. You can venture deeper into each state, discover hidden gems, and take leisurely leaf-peeping detours along the way. This would make for the Ultimate New England Fall Road Trip.
Pro Tip:
Remember that driving between destinations takes time, so factor this into your itinerary. New England’s scenic routes are part of the experience, but they can be slower than highways.
Some Things You Should Know About My Itinerary
Timing During COVID-19:
My New England Fall Road Trip took place in October 2020, a time when the world was still navigating the challenge of COVID-19. While the pandemic did present some unique considerations for travel, it’s worth noting that all the attractions and destinations we visited were open and welcoming visitors. However, there were specific guidelines and restrictions in place to ensure everyone’s safety.
Accommodation Challenges:
One of the biggest complications we encountered during our trip was related to accommodations. Due to the pandemic, some lodgings, including hotels, inns, and even campgrounds, had specific policies in place. Some did not allow out-of-state visitors, while others required a negative COVID-19 test within 72 hours of our reservation.
FYI: If we could navigate our New England Fall Road Trip without advanced reservations during COVID-19, then you should have no problem planning yours today without any, either.
Starts in Boston:
Our adventure began in the city of Boston, where we flew into Logan International Airport. Boston is an excellent launch point for a Fall New England Road Trip, with its iconic attractions, delicious seafood, and cobblestone streets.
A Counterclockwise Road Trip:
Our fall road trip followed a counterclockwise route, covering all six New England states—Massachusetts, Maine, New Hampshire, Vermont, Connecticut, and Rhode Island. Starting in Boston, Massachusetts, we then made our way north, transitioning from the city to the charming towns and landscapes of northern New England. This route offered a wide range of experiences. We explored historic cities, beautiful coastal towns, and mountainous regions.
True Road Trip Style:
My 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. While this might not be your preferred pace, it allowed us to cover a lot of ground and experience all of New England’s landscapes and destinations. Of course, I know everyone has their own style and pace when it comes to traveling. Feel free to change this fall road trip itinerary to your liking. Adjust the number of nights in each location and add or subtract stops based on your interests.
Pro Tip:
Tailor the length of your New England road trip to your interests. For example, if you’re passionate about hiking, you might want to spend more time in the White Mountains of New Hampshire or Vermont’s Green Mountains.
Two Week New England Fall Road Trip Itinerary -Starting in Boston
14 Day Road Trip Overview:
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 Kancamagus Highway and head up to Montgomery, VT
Days 8-10: Explore Stowe, Woodstock & Green Mountains, Vermont
Day 11: Explore the Berkshires, Massachusetts
Day 12: Litchfield Hills & Essex Connecticut
Day 13: Newport, Rhode Island
Day 14: Back to Boston for one Night (Fly Home in the Morning)
Breakdown of Our 14-Day Itinerary:
Day 1 – Arrive in Boston
FYI: We chose to kick off our New England road trip with TWO NIGHTS (One Full Day) 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.
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!)
- 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.
Day 2 – Explore The City of Boston
FYI: Fall foliage peaks later in Boston – usually mid to late October. We did not get any fall foliage in the City of Boston till we came back around on our way home.
Here are the Highlights if You Plan to Start Your Trip in Boston:
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 world’s oldest commissioned warship 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. Sample their famous clam chowder or enjoy a classic seafood dish in a historical setting.
Here are a Few Other Suggestions to Consider:
We did not do these, but I wanted to give you other popular options so you could tailor your visit to your liking.
- Samuel Adams Brewery Tour: If you love beer, take a tour of the Samuel Adams Brewery.
- 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 culinary highlights.
For more of Boston’s top tours and activities, check out Viator or Get Your Guide.
Pro Tip:
One of the best ways to experience Boston is to explore on foot. I found Boston to be a very walkable city filled with quaint streets and hidden gems! When you explore on foot, you have the freedom to stumble upon these lesser-known but equally exciting spots.
Day 3-5: Explore Maine’s Coastline
It’s time to hit the road my friend! How excited are you??
Pick up your rental car, and head up Maine’s coastline first.
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. TIP: Because we didn’t have hotel or campsite reservations in advance, we had the freedom and flexibility to extend our trip in Maine!
Day 3: Salem & York
On your way up the coastline, consider making a pit stop to check out 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 was VERY crowded when we were there! We had a difficult time finding a parking spot. When I say difficult, I mean 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.
CONTINUING ON! Make your way up North along the coastline of Maine.
This drive is 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 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 dispersed camping in this area, we camped at York Beach Camper Park, just outside of town. It wasn’t a free campsite, but it was 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
Along your drive up the coastline, the farther North you go, the better the foliage colors get.
Stop at some of the beautiful lighthouses Maine is known for: Cape Elizabeth Lighthouse and Portland Head Light Lighthouse were a few of our favorites. 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 1.5-pound 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. We were hoping to make it as close to Acadia National Park as we could this night. It was getting late, we were getting tired, and they had open spots and were taking out of staters. 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! Bonus: they had hot showers!
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
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 adorable houses with colorful doors, colorful lobster boats, seafood shacks, and fishermen going about their daily routines. You will get to experience 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 is the town where most travelers choose to stay. It is the base for exploring Acadia National 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 and exploring Acadia National Park, that I just couldn’t shake. So we found a room last minute that had a HOT TUB so I could try to get rid of my chill! Tip: Dress appropriately for the damp weather along the East Coast!
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. I collect snow globes from everywhere I go, and Bar Harbor had a cute all-Christmas store!
- 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:
Consider visiting Acadia National Park during the less crowded times of the day. Tourists flock to popular spots like Cadillac Mountain at sunrise. While sunrise at Cadillac Mountain is a must, you can avoid the crowds and enjoy the stunning views by visiting later in the morning or early afternoon. Additionally, exploring the park’s hiking trails and attractions during off-peak hours can provide a quieter and less crowded experience.
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
FYI: 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!
Also, I should warn you now that I have a bit of an obsession with covered bridges and made an attempt to hunt many of them down along the way. So, basically, I’m saying you will be seeing a lot more of them! Of course, I don’t expect you to have the same obsession as I do, and I’m sure you didn’t come to New England just to see bridges! So, I will be supplying you with plenty of other fascinating things to see as well.
Good? Okay, now let’s move on!
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.
FYI: We found a sweet little spot in the White Mountain National Forest just outside of Jackson to disperse camp that night. Dispersed camping means camping outside of designated camping areas in national forests. There are no amenities, but it’s FREE!
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.
Tips for driving the Kancamagus Highway:
- Once you are on The Knac there are no comforts of the modern world (no bathrooms, no gas stations, no restaurants, and no other businesses), so plan accordingly!
- There is no service, 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, provides scenic views of fall foliage, 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. This was perfect so we could go the bathroom and stretch our legs before we could enter!
Okay – at this point, you have two options. (Well, actually, the options are endless, but I’m only giving you two!)
- 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.
- If you are 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.
FYI: Montgomery is almost 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 concur!! It is a leaf-peeping paradise!
We ate a delicious pizza dinner at a pub in Montgomery and Stealth camped on the outskirts of town for FREE!
Days 8-10: Explore Stowe, Woodstock & Green Mountains, Vermont
Vermont was my favorite New England State, and therefore, we ended up spending three days exploring it.
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.
FYI: About 40 minutes south of Stowe, VT, we found a strip of national forest where we dispersed camp for the night. We were not the only ones dispersed 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.
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 New England fall 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 farms and 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!
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 Cornish Windsor Covered Bridge that I wanted to see the next day!
Day 11: 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 two hours without stops to reach the Berkshires.
- 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.
FYI: We ran out of national forest for dispersed camping options by the time we left Vermont. And instead of trying to stealth camp somewhere for free, we chose to stay at the Hopkins Inn in Litchfield, CT. It was such a cozy little inn with great views of Lake Waramaug. And it was affordable! Highly recommend.
Day 12: 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 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 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 Fall foliage 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 13: 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 more!
The drive from Essex, CT, to Newport, RI, will take you 1 hour 20 minutes with no stops.
Here are the 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 14: 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.
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 chose to spend our last night in Boston eating our fill of delicious lobster at lobster shacks down by the Boston Marina and strolling through the cobblestone streets and shops of The North End. We popped into our favorite pub, Mr Dooley’s, for another pint to celebrate the amazing Fall New England Road Trip we just had! Then we relaxed in our hotel room since we had an early flight in the morning. We chose to stay at the same hotel, Club Quarters Hotel, as we did when we arrived.
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 cold and crisp one minute, then the sun would come out, and then before you know it, it’s dumping rain and freezing! On top of that, the weather can vary quite a bit 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 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 make its appearance.
If you would like Fall Outfit Ideas for travel, check out my Fall packing guide here!
Here are the essentials you should pack for your fall New England 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 be prepared for rain or cooler temperatures with a waterproof jacket.
- 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 or rain poncho for unexpected rain showers.
Tech and Accessories:
- 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:
- Reusable 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.
Remember to tailor your packing list to your specific activities and destinations within New England. With the right clothing and gear, you’ll be well-prepared to enjoy New England during the fall season.
Frequently Asked Questions
Which states in New England are the best for fall foliage?
All New England states offer stunning fall foliage, but some particularly renowned destinations include Vermont’s Green Mountains, New Hampshire’s White Mountains, coastal Maine, and the Berkshires in Massachusetts.
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. These are the fall flavors the region is known for.leaf peeping
Are there any scenic drives to experience the fall foliage?
Yes, New England is famous for its scenic drives during the fall. Consider routes like the Kancamagus Scenic Byway in New Hampshire, the Mohawk Trail in Massachusetts, or the Vermont Route 100.
How can I find the best spots for leaf-peeping?
Research fall foliage prediction maps and local resources before your trip. National and state parks, scenic byways, and hiking trails are excellent places to witness the colorful displays.
What’s the weather like during the fall in New England?
Fall weather in New England can be quite varied. Expect cool mornings and evenings with daytime temperatures ranging from mild to moderately cool. Be prepared for occasional 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 itinerary around your interests, whether it’s hiking, exploring historic sites, or enjoying local cuisine. Leave room for spontaneity, as some of the best experiences come from unexpected discoveries along the way.
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That’s a Wrap for 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, and be sure to leave a comment letting me know how it went.
Happy travels!