New England Fall Road Trip

Hi, I'm sure there will be others that will post here, but I was there with my sister in the fall of 2022 to see the beautiful fall colors. Our trip was limited to Connecticut because we were there for a cousin's wedding, but we stayed in Litchfield, CT for the first portion of the trip and loved it there, and then also visited Glastonbury, CT and spent a night there. We really loved Glastonbury. I remember telling my sister that this was a place I could easily move to. It was just lovely.

So Litchfield and Glastonbury are just a couple that you might want to take a look at. You also might want to use the search function (upper left hand corner) to see what other folks have said here in the past. There are lots of threads about New England on the forum.

Also, Burlington, VT is a wonderful place as well, so you might want to add that. I really enjoyed it, and it has the Ben and Jerry's ice cream factory there and the incredible Shelburne Museum nearby, which was really wonderful and well worth a visit.

If you are planning this trip for Fall 2026, your destinations may depend on where you can find accommodations-of any kind. When we went to NC during leaf season, we reserved our accommodations a year in advance.

This list is incredibly ambitious and definitely not doable in 2-3 weeks time.. Many of these places on your list deserve more than 1 day. You could spend more than 1 day in Boston, Acadia, North Conway/ Franconia Notch. alone. You can group Acadia together with Rockland and Camden but Acadia deserves more than 1 day. You didn't list Bar Harbor, Maine which can be seen in conjunction with Acadia. Franconia Notch, North Conway, Kancamagus Highway are all within a similar area. I think you can cross off Lyndon, Vt and Chester, Ct. You also didn't list Bennington, Vt which is definitely worth a visit. As someone who lives in Ct , I have been to all of these places on your wish list except 2 . For my vacations in New England, I have stayed 1 week each multiple times in Maine, Vermont, Mass. and N.H. I have done the 4 places in Ct on your list as day trips.

Native New Englander here. I would suggest you narrow the scope of your visit to either northern NE (VT/NH/ME) or southern NE. I agree it is too much for 2-3 weeks.
Depending on exactly when you come, the leaves may not be changing significantly in southern NE (with the possible exception of the Berkshires in western MA). So late Sept early Oct would be best for northern NE.

Agree that finding lodging might be your biggest issue but I think it can be done even now. If you belong to AAA, enlist their help in plotting out a driving loop.

I would start my travel by driving to western MA and traveling up the western edge of VT up to Burlington. I agree about adding Burlington VT. Definitely add Shelburne Museum to your must visit list. Use the city as your hub for Stowe and Waterbury. Woodstock as your hub for central VT and western NH (Hanover for example). Longest covered bridge in US? In Windsor VT. Great little museum on precision toolwork and early gun manufacturing - Windsor VT. Most photographed town/farm in VT-Peacham. Tons of B and B's but these may be booked already. One of the best adventures I ever had was a quest to travel only on dirt/gravel roads from my town to Montpelier - approx 60 miles all via dirt road. BTW-our dirt roads are major roads for many towns.

Cross over to NH from central VT to the mountain region. Kangamangus is just a road, very scenic but a road. If you plan on hiking any the the moutains in the north be very aware of weather conditions on the mts. A man just died in the presidentials after underestimating the weather conditions.

Cross over to ME-unless you drive down to southern NH, you are taking secondary roads from NH to ME. This will be the longest travel day due to no interstate driving. I can't really recommend anything in ME since I have not traveled anywhere but Portland and the coast south of Portland.

Yankee Magazine has had many articles on scenic New England foliage trips.

Have fun and hope for great weather.

The litinerary does seem to try to cover too many destinations ( 21 of them) for a 2-3 week trip including 6 states. You would be driving way too much to cover the places on the list and I’m not sure it would make for an enjoyable trip.

My recommendation is to focus on Massachusetts, Vermont, New Hampshire and Maine. Maine is one of the most beautiful states in the U.S. and—if you visit Acadia National Park, Camden, Rockland and Portland— you’ll be seeing some of Maine’s other scenic highlights along the way. West of Acadia National Park on Deer isle is the scenic lobster fishing town of Stonington.

In Vermont, rural Highway 100 runs through the entire length of the state and travels through or near many of Vermont’s most iconic towns such as Weston and Warren. For leaf peeping, the optimal time to be in Vermont is generally the first week of October. Hotel rates can be very high throughout New England during this time as it is part of the tourism high season. The influx of drivers hitting the roads during this time is why you need to be selective about where you choose to visit timewise. You might take a look now at sites such as Booking.com or Hotels.com to get an idea of what rates are like.

Have a great trip!

Hi, I’m also heading to the NE states for the Fall leaves color in early October. I will be going with the Modern Widows Club, and we’re doing a Vermont, Maine, New Hampshire, Massachusetts loop with a tour bus. I have been to all of those states except Vermont. You will have a wonderful time!

Looking at your list, I would suggest a loop similar to the route I will be doing but plan to stay at a coastal town in New Hampshire, too. It’s been several years, so I can’t give you the name of the lovely B&B where my hubby & I stayed.

I would recommend leaving Connecticut & Rhode Island for a second trip, giving them adequate time to really enjoy them. My husband & I had a fantastic time in Connecticut and especially in Newport, RI touring through the magnificent summer homes. (One of them made me smile that the “Do not sit” signs were written in French, even though most visitors now would need it in English.). We finished that trip with several days in NYC - nice variety within one itinerary.

You are trying to do way too much for 2-3 weeks. This is the most popular time in New England and you will run into not only lots of cars but tour buses. Even if you plan to rarely get out of your car or don't mind one night stays, then you will still have a problem hitting all of these places.

As stated, accomodations will be your biggest issue. And be ready for some real sticker shock. Prices will be insane in some areas for whatever accomodations may still be available.

Great advice from others. I agree to delete CT and RI. I suggest pinpointing activities (hikes, museums) that interest you. Also use Google to find out about local festivals you'd like to attend. They're every weekend at that time. We live in SoCal and have traveled a bit around the west and weren't blown away by the scenery at Acadia NP. But Maine is lovely with lots of cute places and you could do a loop BOS, Maine, Kancamangus, some of Vermont or western MA, BOS.

I agree that it will be too early to see fall colors in CT and RI in late September and early October. And although I am about a 15 min. drive from Providence, RI, I wouldn't try to spend that much time there. The area around Brown Univ. is nice and Federal Hill has some great food but you can easily see what you may want to see in a day. If you do want to spend time in RI consider Bristol and Westerly (where Taylor Swift has a house) as well as Newport.

Do you intend to spend any time in Boston? If not, consider flying into and out of Manchester, NH. You're coming from the west coast so your flight will arrive fairly late so even getting to Rockport from Boston may be a slog. If Boston/Logan remains the best travel option, skip Rockport. I love Cape Ann but it may not be worth your time. (Apologies to Wray). Just go straight to Portsmouth.

For your time in ME, consider staying in the Penobscot/ Blue Hill/Brooksville area.

Thank you for all your replies. We’ve taken a lot into consideration and have decided what we are going to look into moving forward, depending on where we can find good accommodations, etc.

I am a native New Englander, too, and have lived here all my life. I agree with everyone else that you cannot possible do what you want to do in 2 to 3 weeks. Even though I grew up in Western Massachusetts, and I love this area, I would suggest omitting MA from your itinerary so that you can concentrate on Maine, Vermont, and NH. These 3 states will have the best fall colors for late September/early October. And what is the sense of rushing from place to place? Do you really want to see the fall colors solely from your car window?

In addition to the places you listed in Vermont, I would include a visit to Norwich, which is about 30 minutes from Woodstock. Norwich has a very pretty center. It's small but that is what makes it charming. If you love baking, you can visit the King Arthur Flour Company and have a delicious lunch here. There is a very nice farmer's market on Saturdays. In the center, there is the wonderful Norwich bookstore, Dan & Whit's General Store (motto: if we don't have it, you don't need it), and the Norwich Inn. Full disclosure: I think the Inn has mediocre dinners, but it's a warm and inviting place to have a drink and appetizers. If it's warm enough, the Inn has a charming, covered porch where you can have drinks.

If you fly into Boston, and then head straight north to NH, you can make a stop in Rockport, MA along the way, time willing.

If you stop in Norwich, and you have the time, you can then meander over to Hanover, NH, home of Dartmouth College. Hanover is a 10 minute drive from Norwich. Interesting shops, lots of restaurant choices. A pretty town with the lovely campus in the center.

If you omit Western MA from this trip, you can still logically reach Burlington, VT from Norwich or Woodstock. It's about a 1.5 hour drive from Woodstock.

If you come to New England another time, that would be a good time to visit MA, CT and RI.

Two other suggestions for VT: The upper northeast corner of the state is called the Northeast KIngdom (NEK). Base in St. Johnsbury or nearby. Visit Dog Mountain (an homage to all things dog, including a chapel for deceased pets), the Fairbanks Museum, and a nice downtown. Lake Willoughby is an incredible lake (Google for images) within easy driving distance as are the towns of Greensboro, Craftsbury, Hardwick.

The other suggestion is White River Jct. (WRJ). Easy drive from Woodstock or base here and day trip from here. Quirky downtown with an equally quirky museum called Main Street Museum (very difficult to describe), active rail station, Center for Cartoon Studies (a MFA program for cartooning), and restaurants/cafes. Norwich is the next town north of WRJ. King Arthur is a big a attraction year round but I find the cafe very noisy. If you are into baking check out offerings for classes.

I lived in Norwich for over 40 yrs (currently in WRJ). Dan and Whit's is a longstanding fixture in town. If you go be sure to go to the backrooms. There you'll find cow licks, horse feed, and other misc. objects. Most people don't realize there are back rooms (you need to walk between the beer coolers and the deli space. D&W also has THE BEST BREAKFAST SANDWICH in the state. Norwich also has many hiking trails. Google the town's website.