It is officially that time of the year. People start closing their windows, the sunsets are earlier and earlier and the leaves change to all kinds of beautiful colors. There are so many incredible places in the United States to enjoy the fall colors (also known as leaf peeping), but none can compare to New England. By taking a New England fall road trip, you’ll be rewarded with fall colors acting as a backdrop to the quaint towns and covered bridges, tons of maple syrup and some great beer. It honestly feels like you are in a movie set that was created just for the enjoyment of visitors with everything perfectly fitting the part.
It’s been fun to relive our trips to New England while putting this together. It’s embarrassing how many photos I have of trees, but then I can’t bring myself to delete any of them. Don’t worry, I’m not sharing everything here – just a few to give you an idea and convince you to plan your New England fall road trip.
A Few Notes on Planning Your New England Fall Road Trip
- You can start anywhere there is an airport. The map I included started in Albany and ended in Boston, but you can loop through Rhode Island and Connecticut or even start and end in New York City. New England isn’t too big, so you might save a lot on airfare to try different airports.
- Check the Peak Foliage Map for the area you want to visit. If you are planning for next year, check the last few years to see which weeks were peak. You may not plan it perfectly, but the good news is that the area is still GORGEOUS.
Alright, let’s dive into the full list of places to visit. The guide for a New England fall road trip is broken down by state. I included places we have stayed and loved to help take some of the extra work out of it.
A Seven Day/Six Night New England Fall Road Trip Itinerary
Vermont – Day 1
Vermont is so much more than the home of Bernie Sanders. The Green Mountains run north-south through the state and you will find covered bridges around every curve. In the winter, it’s an amazing ski destination with some classic resorts, but in the fall, you can see the mountainsides covered with different colors.
100 Mile View at Hogback Mountain
Hogback Mountain was a perfect spot to kick off a New England fall road trip. With coffees in hand, we pulled over to this viewpoint and just allowed ourselves to get giddy about what was to come in the week ahead. From this viewpoint on a clear day, you can see Vermont, Massachusetts, and New Hampshire. If you are ready to stretch your legs, take a hike to the headwaters of the Green River.
Townsend, VT
This town may not be on the radar for many people, but we could not miss the opportunity to visit. One of our favorite movies was filmed in this town. If you are a fan of Chevy Chase, hopefully, you have already seen Funny Farm which takes place in the fictional town of Red Bud. It tells the story of a big city couple that moves to small-town life in Vermont and the comedy of errors that comes with that transition. It’s a classic fish out of water story with the incredible backdrop of Vermont. It’s the perfect complement to this road trip. The town itself is adorable and picturesque and by detouring here, you’ll be able to stay off the main highway.
Harpoon Brewery in Windsor
In Windsor, check out the Harpoon brewery with bonfires outside and a huge selection of beers on tap. In the same parking lot, you’ll also find a great outfitters shop and a distillery. It’s a great place to take an afternoon break and try a flight of beers and some great snacks. Pop into Blake Hill Preserves and grab some things to keep in your car cooler to snack on while on your New England fall road trip.
Spend the Night in Woodstock or Nearby
In Woodstock, there are quite a few inns, like the beautiful Lincoln Inn, which also has a wonderful restaurant attached. Find a cozy spot for dinner in town. There is so much that is walkable in Woodstock.
Vermont – Day 2
Grab Breakfast in Woodstock
There are some incredible coffee spots and breakfast in town. We ate at the Mountain Creamery and enjoyed bagels topped with apple and Vermont cheddar cheese. If you’re lucky like we were, you might get a perfect foggy morning to do some window shopping. This town feels like it belongs in a fairy tale so make sure to enjoy it a little before moving on. Walk the covered bridges in town and pick out which of the adorable houses you could see yourself living in.
Stop in for Lunch at Long Trail Brewery
Just outside of Woodstock is Long Trail Brewery. It was one of our favorite breweries in Vermont. There is a great backyard where you can sit outside. Grab a growler to go so you can enjoy it later if it’s still too early in the day for a beer. Our favorite is the classic Long Trail Pale Ale.
Take the Gondola at Killington
Killington Ski Resort is located just west of Woodstock. Even before the snow flies and ski season kicks off, you can take advantage of the gondola and head to the top of the mountain for some incredible 360-degree views. There are quite a few hikes to enjoy if you want to get in your exercise.
Head North on Route 100
Route 100 is an essential part of your New England fall road trip. You will cruise through a beautiful valley with mountains all around you. There will be small farm stands, beautiful fall colors, and even a covered bridge or ten. Make sure you have a good playlist and enjoy the scenery. Road trips are the best because you can go as fast or as slow as you want.
Spend the Rest of Your Evening in Stowe
Stowe, Vermont, is a beautiful town with tons to do. If you have an extra day, spend two nights here with a whole day to explore. The Ben & Jerry’s factory is here. You can take a full tour complete with samples. We didn’t have time, so we just visited the company store and the flavor graveyard.
You can also visit the Von Trapp Family Lodge just outside of town. They brew their own beers there, and you can order a flight to enjoy while taking in the scenery. We watched goats play in the pasture before us and learned about the Von Trapp family’s relocation to Vermont. Check out the options to spend the night here as well.
We stayed at the beautiful Stowe Mountain Resort, and I would have loved to extend our stay here. It was beautiful and so comfortable. It helps that they upgraded us when we arrived to a suite.
Other Vermont Favorites
If you want to do more exploring in the beautiful Green Mountain state, you can go off course and visit our other favorite places in the state.
Rutland
Rutland is a great winter spot to stay. It’s a tiny town close to a few ski spots. But the main highlight for us there is the Rustic Rooster. A woman named Donna moved from the big city to the mountains of Vermont and opened this wonderful little restaurant. We ate there three days in a row and were treated to different daily specials. Even as vegetarians, we were able to indulge. Try a Donna-tini cocktail and make sure to chat with her for a while. There are a few great AirBnBs right in the little town, so it makes for the perfect weekend escape.
Burlington
This is one of the only “cities” in Vermont and it’s a wonderful place to hang out for a weekend. The downtown area has a great variety of restaurants and bars to choose from. You can also use the airport here to fly into because it has a surprising amount of flight options.
Day 3 – Vermont/New Hampshire
Get Up Early and Grab Coffee to Hit the Road
Drive into town and grab a coffee before making the trek to New Hampshire. You’re going to have a giant brunch, but you can have a little pastry or something to hold you over. Stowe Bee Bakery & Cafe and Cafe on Main are two popular coffee spots.
Make the Drive to Polly’s Pancake Parlor
Located about 90 minutes from Stowe, Polly’s Pancake Parlor is an incredible place to spot for food. It opened in 1938 as a way for the family to highlight their maple products. It’s grown in popularity over time, and it’s best to visit on a weekday for a shorter wait. We shared our table with another couple and ordered the variety plate with a collection of their top-selling cakes. There is no picture of the actual pancakes because we were hungry.
I would also recommend leaving with as much pancake mix and syrup that you can fit into your suitcase. We enjoyed Polly’s for weeks after our trip and it wasn’t quite as good when we made it ourselves, but a fun reminder of this magical trip.
Stop to Stretch Your Legs at Franconia Notch State Park
If you need to work off some of the pancakes you ate, visit Franconia Notch State Park. There are tons of great trails to hike in the area and beautiful scenery. Unfortunately, we had a very rainy day when we left Polly’s, so we just pulled off and did some quick runs out of the car to explore. It’s definitely on my list to come back.
Kancamagus Highway
The Kancamagus Highway is the pinnacle of this leaf-peeping trip. When we first told my dad about our plans for this trip, he said we absolutely had to take the 34-mile stretch of Route 112 called the Kancamagus Highway. He quickly said it was one of the most beautiful drives he had ever taken. It has made the list of the Best US Road Trips in many different publications.
We circled back around later in the day when it had dried out a little, but I would cruise this route no matter what the weather. It was incredible. There were a few places to pull over and enjoy the views of the White Mountains covered in a variety of different fall colors. It was breathtaking.
Check Into Your Jackson B&B
We spent two nights at this wonderful bed and breakfast in Jackson. We could not get over the coziness of this place with fun wallpaper, a large front porch, a gorgeous fireplace, and an insanely good breakfast each morning. Don’t miss out on the freshly baked cookies that are sitting out each evening. It’s everything cozy in one spot.
Day 4 – New Hampshire
We chose to stay in the same place for two nights so we could avoid that travel burnout that comes with repacking and moving on every single night. Jackson was a great place to do that because there is so much to explore near there.
Mount Washington Auto Road
The Mount Washington Auto Road was first opened in August of 1861, making it one of the oldest man-made attractions in the United States. The road winds up Mt. Washington and offers some of the best views of the White Mountains.
Our drive was a little scary because the fog was so thick when we headed up. It was hard to see very far in front of the car. We were so bummed that we had wasted money, but in a few minutes, the clouds started moving, like a curtain opening with the most beautiful scenery behind it.
If you want to skip the drive, you can take the Cog Railway up to the top or sign up for a guided drive where you just get to ride along with a guide.
Give Yourself a Relaxing Afternoon With Views
You may be staying in a quaint B&B, but that doesn’t mean you can’t spend the afternoon soaking in the luxury and views at the Omni Mount Washington Resort. Take advantage of the spa services or the dining areas that are open to the public.
Take a Late Afternoon Hike at Hall’s Ledge
If you want a little more adventure, check out the 5-mile roundtrip trail at Hall’s Ledge. You’ll get some views of Mount Washington and you may even catch a glimpse of a moose later in the day. Keep an eye on the time with sunset to make sure that you allow yourself time to get back before it’s dark. Check AllTrails for more hikes if you want something shorter or longer.
Day 5 – New Hampshire/Maine
Enjoy the Drive
Grab your breakfast at the B&B and some coffees to go and hit the road towards the coast. The small highways that cut through New Hampshire and Maine are beautiful. You will pass by beautiful, calm lakes and through all kinds of small towns. We didn’t make many stops because it was one of our longer drives, but you could find some great spots to stop and picnic.
Bar Harbor
My biggest regret of the trip is not including an extra night in Bar Harbor to enjoy Acadia National Park. I cannot wait to return again in the future. We were a little overwhelmed when we arrived in Bar Harbor due to the cruise ships that had just docked. There were people everywhere. It’s such a beautiful town, and I think our timing was just off.
We did enjoy a local beer called the Leef Peeper, from Atlantic Brewery, and some incredible clam chowder and crab cakes. After lunch, we just walked off our food by doing some window shopping and enjoying the beautiful harbor area. We only stayed for the afternoon.
Camden
Camden is the little harbor town where we spent the night. The Lord Camden Inn was fantastic. After checking in, we strolled along the tiny Main Street and picked out our dinner spot. Our main goal was Lobster, and it was served everywhere. I had only ever eaten lobster rolls and lobster in other dishes like pasta. This was my first experience where it was just cooked and served on the plate. I did not love it, but I am so happy I tried it. Another great food option in town is Cappy’s Chowder in the Sea Dog Brew Pub.
Day 6 – Maine/New Hampshire
Our plan for the day was to head south down the coast with no real agenda. We hoped for a beautiful rocky coastline drive, but this is not the Pacific Coast Highway. You have to detour a lot for those postcard moments. We did find a few gems, though.
Mount Battie Sunrise Hike
A sunrise hike is not everyone’s idea of a good time, but if you are going to do one on your trip, make it this one. Set your alarm and head out of the hotel going north. You’ll find a trail that takes you through the woods to the top of Mount Battie, and you’ll have a gorgeous view of the entire town and harbor area as the sun comes up over the ocean. The lookout area can also be reached by car if you overslept or don’t want the morning sweat.
Portland
This is another spot that I would love to return to for a little more time. We just stopped for some beers at Shipwreck Brewery and to stretch our legs a bit. There are so many great walkable areas in town where you can do some shopping or find a great lunch spot (although save some room for the next stop).
Kennebunkport
Kennebunkport is an adorable town that came highly recommended. We cruised past the Bush Compound that sits out on the water. There were some insane oceanfront mansions in town. Our food stop was at the Clam Shack, and I still think about that meal years later. The Fried Clam Sandwich was suggested by quite a few of our friends, and it did NOT DISAPPOINT. The shack sits over the water and has a pretty simple menu, but if you want some good seafood without any fancy fanfare, this is the place for you.
Portsmouth, NH
We arrived in Portsmouth, New Hampshire, at the end of our day and checked into a small hotel there in time to wander around and explore a bit. We met a friend for beers and got to recap our incredible week. This was the perfect place to end our trip.
Other Notable Spots for a New England Fall Road Trip
Salem, Massachusetts
This town is famous for the Salem Witch Trials and really puts on a show for the Halloween season. If you like history and want to include a little spookiness to your trip, it’s a short drive from Portsmouth and would be on the way if you were flying out of Boston.
The Berkshires
In northern Connecticut and Western Massachusetts, the Berkshires is a region with rolling hills and historical New England towns spread throughout the countryside. You’ll feel like you’ve been dropped right into a Norman Rockwell painting.
Woodstock, New York
The Catskills Region is one of our favorites, and we tried to visit at least twice a year. If you’re looking for something closer to New York City, this is less than two hours and serves up some incredible fall colors.
New England Fall Road Trip Map
Pin these to help you plan your New England fall road trip
And make sure to tag us in any of your photos. We always love a good road trip.
