The Ultimate New England Fall Road Trip Itinerary: 5 Days of Scenic Drives, Leaf Peeping & Charming Towns
View from the Woodstock Inn
If you’re dreaming of the perfect fall foliage road trip in New England, this 5-day itinerary will take you through all six states: Massachusetts, Rhode Island, Connecticut, Vermont, New Hampshire, and Maine. Think covered bridges, charming coastal towns, historic landmarks, and some of the best fall colors in the U.S.
For years, my sister and I traveled to Paris every fall, but in 2020 we decided to explore closer to home. After researching the best places to visit in the U.S. for fall foliage, one destination kept coming up again and again, New England in the fall. We booked a four-night trip, and it was so magical that we’ve returned every year since.
This guide will help you plan your own New England fall road trip, with tips on when to go, how to get around, where to stay, and all the must-see fall attractions.
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GETTING to new england for your fall road trip
Most travelers will want to fly into Boston Logan International Airport (BOS). Every major U.S. airline service Boston, and it’s the most convenient starting point for a New England scenic drive itinerary. Keep in mind: flights get expensive in peak foliage season (late September through October), so try to book by July or August.
Pro Tip: You’ll absolutely need a car for this trip. Reserve your rental early since prices skyrocket in September and October.
best time to visit new england for fall foliage
The most common question is: When is peak fall foliage in New England?
Peak season typically runs from late September through mid-October, but exact timing depends on weather and location:
Northern New England (Vermont, New Hampshire, Maine): Late September – early October
Southern New England (Massachusetts, Connecticut, Rhode Island): Mid to late October
Use the New England fall foliage map as a guide when planning, but remember, leaves change differently each year depending on rainfall and temperatures. A great tip is to plan your visit about a week after peak foliage predictions for the most vibrant colors.
There are several foliage prediction maps we referred to while planning which days to visit. I recommend checking each of them early and often.
This Fall Foliage map shows New England as a whole. Just toggle back and forth to see peak dates.
This foliage prediction map is exclusively for New Hampshire
This foliage prediction map is for Vermont. You can sign up to get updated foliage reports at this website which I’ve been checking every week this month.
If you’re visiting Maine on your trip, you’ll want to check this foliage map.
Massachusetts fall foliage predictor map
Remember, the map is just a guide and that foliage color is based on many factors including summer temps and rainfall. We booked our second trip based on the map saying it was peak foliage when in fact it was probably still a week or two away. When in doubt, book your trip for a week after peak foliage. For us, we were able to see much more color by arriving a week later.
Day 1: Boston → Newport, Rhode Island → Mystic, Connecticut
After arriving in Boston, we picked up our rental car and headed south towards Mystic Connecticut. We knew we wanted to stop over for a few hours to explore Newport, Rhode Island, especially since it’s just an hour away from Boston. Traffic was pretty terrible getting out of Boston, so it took us a couple of hours to get to Newport.
Newport is a gorgeous coastal town best known for its Gilded Age mansions and cliff walk along the coast. It was starting to get dark when we arrived (remember in the Fall it gets dark close to 5p.m.) so we did a quick drive by the mansions, headed to the historic waterfront to explore the shops and grab a bite to eat. It was fun to see the boats heading in with just a bit of fog coming off the water. Trees were bright orange with color. Newport definitely deserves more time than what we gave it. After exploring downtown, we hopped in the car and headed to Mystic, Connecticut which was just an hour drive away.
Where to stay in and around Mystic, CT:
Hyatt Place Mystic: This is where we stayed using a Hyatt free night award. Just a short 5 minute drive to the historic Mystic and the Seaport Museum.
Holiday Inn Express Mystic: Great location, pool, free breakfast and some rooms have 2 queen beds.
Residence Inn Mystic: I love a good Residence Inn with a kitchen and happy hour.
DAY TWO: EXPLORE MYSTIC, CT DRIVE TO WOODSTOCK, VERMONT
While most people have probably heard of Mystic, Connecticut because of the popular Julia Roberts movie from the 1980’s, there is so much more than pizza in this seaside town that makes it worth a spot on your New England Road trip. It has an adorable downtown with shops right on the water and a drawbridge.
We had dinner at Mystic Pizza the night before (because you can’t come here without doing that!) and spent the day at the Mystic Seaport Museum which is a recreation of a 1900’s Seaport village. We felt like we had walked back in time exploring the old cabins, schoolhouse, bank and lighthouse. Trees were orange and yellow and there were pumpkins everywhere. The museum is totally Instagrammable. Put this on your list and plan to spend 1-2 hours.
By lunchtime we were hungry and stopped to eat the famous lobster rolls at the Seaview Snack Bar. I’m not a very adventurous eater, but my sister confirmed these were some of the best she’s ever eaten.
Next, we headed north towards Woodstock, Vermont. Although we had no planned stops on our agenda, our motto is always “if it looks pretty, we’re stopping”. So, what should have been a three-and-a-half-hour drive turned into a five-hour drive. But it was totally worth it.
The further north we drove, the more brilliant the leaf colors became. We made a quick detour in Amherst, MA to check out the home of poet Emily Dickinson. Unfortunately, the home/museum was closed due to the pandemic, but we were able to walk around the property and peek in the windows. Amherst was such a cute college town and the foliage was amazing that we parked and walked around for a little bit.
We made one more quick stop in Brattleboro, VT before continuing on to Woodstock. I wish I had done more research on Brattleboro. It was so cute. When my sister and I went to bed that night, we turned on the tv and the Hallmark movie that was on was set in Brattleboro. No kidding!
WOODSTOCK, VERMONT
We pulled into Woodstock and felt like we had stepped into a Hallmark movie. White church steeples, covered bridges, orange and yellow trees, pumpkins everywhere. What a dream. I can’t think of a better place to do leaf peeping. Now if you have followed me on Instagram for a while you know I’m pretty conservative when I choose hotels. I really like to stretch my dollars.
In Woodstock, my sister splurged (it was her birthday) and booked the Woodstock Inn for us. Our room was so big, two huge beds with the fluffiest down comforters I have ever slept in. The bathroom was like a spa. I emailed the hotel before our arrival and the staff was kind enough to leave a sweet note and some treats for her birthday in the room. You can find my hotel upgrade email template here.
On our second visit, my daughter and stayed at The Vesper B&B. It was super cute and steps from everything. Room rate included a generous breakfast.
Where to stay in and around Woodstock, Vermont:
The Village Inn of Woodstock: If you’re looking for an adorable place to stay within walking distance of all Woodstock has to offer, this property is amazing.
The Woodstocker B&B: Great location, short walk to downtown Woodstock
On the River Inn: This property sits just west of Woodstock but it’s riverfront and you will be surrounded by gorgeous fall color. It has an indoor heated pool.
There is a Holiday Inn Express about 10 miles away. May be worth it for a lower price and if award nights are available.
MUST SEE IN WOODSTOCK
Covered Bridges: There are four covered bridges in the Woodstock area. One is right in the middle of town, the Middle Bridge. It’s right across the street from the Woodstock Inn. Then there is the Taftsville Bridge. This bridge is east of Woodstock. It’s bright red and hard to miss. Built in 1836 it’s one of the oldest covered bridges in the nation. Lincoln Bridge is west of Woodstock and the Quechee Bridge east of town near the entrance to Quechee. We were short on time and just visited Middle Bridge and Taftsville Bridge.
Sleepy Hollow Farm: Updated: Since our visit the road to this farm has been closed during peak fall foliage season. We saw photos of this farm everywhere on social media and knew we really wanted to see it. The drive to the farm was amazing. Narrow, winding roads lined with trees of orange and yellow. When we found the farm we were shocked that there were no cars there. We had the place to ourselves for a good ten minutes before the next car arrived. Another reason why visiting post-peak is a good idea. There is a small arm gate blocking the driveway so you can’t go down, but the views are worth the drive.
QUECHEE GORGE: This one is right off the highway so there’s no detour involved. Just east of Woodstock, the Gorge can be seen off of Bridge #4. You can’t miss it, just look for all the people on the bridge.
IF YOU HAVE MORE TIME:
Sugarbush Farm: This little family farm is tucked away in the hills and is so idyllic. Great stop close to Woodstock. Learn how maple syrup is made.
Billings Farm and Museum: This is a working dairy farm where you can view demonstrations and learn about Vermont Farming.
DAY THREE: WOODSTOCK, VERMONT TO PORTLAND, MAINE
After exploring Woodstock, we hit the road and headed to Portland, Maine. The drive was just under three hours, and we got to see all the beautiful fall colors in New Hampshire.
In Portland, we used our free Hyatt night certificate to stay at the Hyatt Place Portland - Old Port. This hotel couldn’t be in a better location - just steps from the port, shops and restaurants. Breakfast is included.
I loved staying in the historic Old Port. Cobblestone streets, old red brick buildings, charming shops and restaurants. Our hotel was a block or two from the waterfront. We explored the old town, walked along the waterfront, ate more lobster rolls and fish and chips and watched the crab boats come in.
If you visit Vermont, you can't leave without seeing a covered bridge. In Maine, you can’t leave without seeing a lighthouse. Luckily, one of the most popular and beautiful lighthouses is right in Portland, the Portland Head Light. Dating back to 1791, this is Maine’s oldest lighthouse. Just a short drive from Old Port, the lighthouse is located within Fort Williams Park.
You do have to pay to park here (don’t try to get away with not paying, there are attendants in the lot that are watching). As you approach the lighthouse, you’ll see a walking path going to the left and right. I recommend walking down each way to get different views of the lighthouse. If you’re in Portland on a clear, sunny day, head here during sunset for amazing views.
Where to stay in Portland, Maine:
Hyatt Place Portland Downtown - Old Port Square: We’ve stayed here twice back when you could redeem your Hyatt free night award. It has a great location, free break and large rooms.
Hilton Garden Inn Hilton Downtown Waterfront: This property has sea view rooms, right on the waterfront, steps from everything.
Courtyard by Marriott: This property is in Old Port, but sometimes prices out cheaper than the other - and you may get lucky and find award nights available.
DAY FOUR: PORTLAND, MAINE TO BOSTON
Today our final destination was the small town of Concord, Massachusetts just outside of Boston. We are big American history fans and wanted to visit the town where the American Revolution started. But in true road trip fashion we made a few stops along the way.
Just forty minutes south of Portland, Maine is the coastal town of Kennebunkport, Maine. The fall colors here were some of the best we saw the entire trip. We parked just off the main street in Dock Square and walked around. There are so many cute shops and restaurants. We spent just about an hour here before heading to the beach for a quick walk to get our toes in the sand.
Because we were visiting New England during the last week of October, we knew we wanted to pop by Salem, Massachusetts just outside of Boston to check out their fall and Halloween sights. Salem in October does not disappoint. We just happened to visit on the day of their big Halloween festival. We weren’t prepared for the huge crowds, so we just did a few drive-by’s of the top sights on our list and continued on to Concord, Mass.
If you love halloween and hocus pocus like i do, Read my Guide to Visiting Salem in October here
Ropes Mansion: If you love the Halloween movie Hocus Pocus, stop in Salem, Mass to see several film locations from the movie.
If you’re planning the perfect fall road trip through New England, don’t miss the chance to take a spine‑tingling ghost tour along the way. In Salem, US Ghost Adventures offers chilling tales of witch trials and haunted history you won’t forget. And in Boston, Boston Ghosts walks you through dark alleyways and eerie landmarks, telling Boston's most haunted tales.
CONCORD AND LEXINGTON, MASSACHUSETTS
We visited Concord to explore the Minute Man National Historical Park and were shocked to find the absolutely cutest New England town. This should be high on your list when visiting the Boston area (it’s just a 30-minute drive outside of Boston). The tree foliage was bright orange; there were white church steeples and homes dating back to the Colonial Period. We fell in love.
The Minute Man National Historical Park is about six miles long and details the events leading up the American Revolution. We saw the site where Paul Revere was captured and took a ranger led tour of the North Bridge to hear about the ‘shot heard ‘round the world’ that started the Revolution.
If you're a fan of Little Women, you must visit The Orchard House
Concord was also home to many of our country's most beloved authors. We toured the home of Louisa May Alcott, the Orchard House (c. 1650). It’s the home she lived in when she wrote Little Women. Also, just a short drive from Concord is Walden Pond. This is where Henry David Thoreau lived in a small cabin for two years and wrote many of his great works.
Seriously. Can you even handle it? I want to go back right now.
Where to stay in and around Concord, Mass:
I think Concord is the cutest New England town. It has a cute main street, history dating to pre-revolutionary times and the homes are gorgeous and there’s so much to see. We didn’t stay here on our first trip, but we did go back a year later and stayed longer. I really think many people don’t think about coming here but the fall foliage was stunning! It’s just so cute. Put it on your list.
Concords Colonial Inn: This is the cutest Inn and the only lodging in the historic city. It sits right on Monument Square so you can walk to everything. Dates back to 1716
Element Lexington: Sits between Concord and Lexington so it’s a perfect homebase when visiting all things American Revolution. A 10 min drive to Concord.
Aloft Lexington: Right next door to the Element Lexington.
Residence Inn Concord: We stayed here in 2021 because we were able to redeem a free night award. It’s a beautiful hotel, a short drive to Concord, but it is in an office complex so you won’t get the charm of staying in town.
DAY FIVE: BOSTON
Spend your last day exploring Boston in the fall. Head to Beacon Hill, where cobblestone streets and brick townhomes are decorated with pumpkins and autumn wreaths. Don’t miss Acorn Street, one of the most photographed streets in America.
TIPS FOR YOUR TRIP:
WHAT TO WEAR: Fall in New England can be chilly and rainy. I don’t like to carry an umbrella around so I pack a good rain jacket with a drawstring hood. Make sure you wear rain boots or shoes that can get wet. Viewing fall colors means you’ll be outside a lot and remember the old saying “there’s no such thing as bad weather, only unsuitable clothing”.
NO SERVICE: Download Google Maps for the areas you’ll be visiting. There were many times we were driving down country roads where we had no service at all and just had to drive until we had service again to find out where we were. Learn from our mistakes and be prepared for being offline.
BOOK EARLY: Hotels book up quickly during peak Fall foliage. If you wait until the last minute you may find the town you want to stay in completely sold out! We booked our rooms in late July/early August and over 80% of lodging in the smaller towns were already sold out.
TRAVEL MIDWEEK: There is a huge difference in crowds (and hotel prices) during the week versus the weekend. If you have a flexible schedule, I highly recommend New England during the week.
SHORT ON TIME? After Woodstock, skip Maine and drive the Kancamagus Highway through New Hampshire on the way back to Boston. You’ll see some amazing color on this scenic by-way including roaring rivers and several covered bridges. You can read my Four Day New England Road Trip Guide here.
Final Thoughts: Why New England is the Best Fall Road Trip in the U.S.
From scenic drives through Vermont and New Hampshire to quaint towns in Rhode Island, Connecticut, and Maine, there’s no better place to experience autumn than New England in the fall. Whether you’re chasing peak foliage, covered bridges, pumpkin patches, or coastal lighthouses, this New England fall itinerary has it all.
Pack your camera, book your hotels early, and get ready for the leaf-peeping road trip of a lifetime.
Happy Travels!
Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.
