THE PERFECT FALL IN NEW ENGLAND ROAD TRIP ITINERARY
Every Fall for the past four years my sister and I have gone to Paris. Free flights, free hotels, it was easy. During 2020, our fall Paris trip was obviously not going to happen because of the pandemic. When we started researching best places to visit in the U.S. in the Fall one place kept popping up. New England! While both of us had visited Boston several times in the summer, neither of us had visited New England in the Fall. We booked a four-night trip and were able to visit all six New England states in five days. We loved it so much; we returned in 2021, 2022 and I’m heading back in 2024.
GETTING HERE
If you don’t live within driving distance of New England, Boston Airport is where you’ll want to fly into. Every national carrier flies into Boston. We booked our flights with points on American Airlines. Flights can be expensive since visiting for Fall Foliage is very popular. I recommend booking flights by late July/August.
You have to have a car for this itinerary. Book this one early. Like flights, car rental prices also rise sharply in September/October.
WHEN IS THE BEST TIME TO VISIT TO SEE FALL COLORS?
We have visited New England three times in the Fall. The first trip we visited a week or so after peak fall foliage. It was stunning. Because we visited lower states like Rhode Island and Connecticut which were just hitting their peak season, we were able to see leaves in all stages of color over our six state road trip. On our second trip in 2021, we timed it a little too early. The leaves were beginning to turn, but we had to drive as far north as we could in Vermont and New Hampshire to really see the color. One our third trip, heavy rain meants a lot of leaves had fallen.
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 maps 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 ONE: BOSTON TO MYSTIC, CT
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. We used points to stay free in Mystic at the Hyatt Place Mystic.
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, school house, 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.
While there are no points hotels in the town of Woodstock, I did find a Holiday Inn and a Fairfield Inn less than ten miles away that you can book with points.
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 sugar 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.
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 in 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.
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.
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.
DAY FIVE: BOSTON
We had just a few hours to enjoy Boston before we flew out. We headed to Beacon Hill where the homes were all decked out for Halloween. Don’t forget to stop by one of Boston’s most Instagrammable streets, Acorn Street. These homes are occupied so be respectful and don’t step onto any of the porches.
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”.
WHAT TO EAT: You’re going to be spending a lot of time in the car on this road trip. We stopped at the store and bought a case of water for the trunk and lots of good road trip snacks. We bought a loaf of bread and peanut butter for impromptu picnics. You don’t wanna get hangry on your road trip.
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 week-end. 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 roarding rivers and several covered bridges.
Happy Travels!
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