The summer heat is starting to give way to the cool autumn breeze. One of the quintessential events that mark the start of the fall season is the changing of the leaves from the vibrant green color to the varying hues of red and orange.
It will be a bit longer before we start to see that here in the South, for those looking for a classic Fall In New England experience, it’s time to finalize plans to head on up North for the annual pageant of natural beauty.
New England is the region of the Northeast United States that is comprised of six states: Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island and Vermont. The area is rich in American history and culture, which makes for an excellent destination.
For a 6 day driving trip around New England in the fall, here’s a my suggested itinerary based on a trip I took with a good friend to celebrate her 50th birthday.
The main goals of the trip are to view the gorgeous foliage as well as to absorb and bask in the atmosphere of fall in New England. This itinerary also has stops for those with an interest in art, literature, and architecture as well as American culture and history. Accommodations, whenever possible, are done via Airbnb or traditional bed and breakfasts, in order to have the opportunity to interact with residents to experience being a temporary local.
Trip Itinerary: Fall In New England
- Arrive in the morning at Boston Logan International Airport.
- Rent a car.
- Drive to Cambridge to visit Harvard University (approx. 20-30 mins).
If you’re lucky as we were, you might chance upon a event like the Head of the Charles Regatta, an annual event where the best crew teams participate in a rowing competition along the Charles River. This year, it’s happening on Oct. 17-18. It’s one of the preppiest experiences I’ve had, watching athletic young men and women from Ivy League universities, prep schools and other upper crust clubs pull on their oars for the prestige of winning the title.
- Head down to Harvard Square for an early lunch at Beat Brasserie, a hippy-trippy restaurant in the heart of Cambridge that serves great food with a seasonal menu and craft cocktails in a grown up-beatnik ambiance.
- Cross the street for dessert at Sweet Cupcakes, another homegrown favorite, making some of Boston’s best cupcakes with fancy ingredients like Callebaut chocolate, Madagascar bourbon vanilla, and Bensdorp cocoa.
- Walk off the calories around Harvard Square. You can take the free student-led Official Historical Tour of Harvard Yard for glimpse inside the hallowed grounds of this prestigious academic institution.
- Leave before rush hour and drive down to Providence, RI (approx. 1h 15m). Drive around and take in the architecture of the city.
If you happen to be there at the right weekend, you might catch Waterfire, an elaborate art installation compromised of sparkling bonfires on the three rivers in downtown Providence. Firetenders on torch-lit vessels make their way on the water while music and performances take place around Waterplace Park. Check the schedule of full lighting events here.
- Head further south to your Airbnb accommodation for the night. I suggest finding a place either in the East Greenwich area or in Newport. I highly recommend booking a room in Michael’s lovely cottage by the Greenwich Bay. If you’re feeling adventurous, try the outdoor shower by the side of the house.
- Wake up early and walk around the neighborhood. If you stayed with Michael, you can walk over to Greenwich Bay and sit by the water’s edge for a serene start to your day. Your host can give you suggestions for a great local place for a quick breakfast.
- Drive down to Newport (approx. 40 mins).
- Visit the opulent summer homes of America’s richest families during the late 19th century. Depending on your time and interest, you can visit one or more of these mansions. If you had to choose just one, visit the Breakers, the Vanderbilts’ lavish mansion that epitomized the decadent luxury of the Gilded Age in American history.
- After salivating over the sumptuous interiors of the mansion, partake in the freshest catch at one of the restaurants in Bowen’s Wharf for a late lunch. Walk around the area and enjoy the quaint shops.
If you go on Oct 16-17 this year, you’ll catch the 25th annual Seafood Festival where good music goes great with New England classics like clam chowder and lobster bisque.
- Leave before sunset for a twilight to evening drive to New Haven, CT (approx. 2 hrs).
- Have a quick bite at one of the oldest and best pizza joints in the country, Frank Pepe’s.
- Stay at an Airbnb apartment near Yale for the night for a collegiate feel.
- Take a seat and have coffee and a breakfast pastry among Yalies at Blue State, Jojo’s or Claire’s Corner Copia.
- Depending on your time and energy, you could walk or drive around the dignified buildings of Yale University. Stop by the Visitors’ Center for a map if you want to do a self-guided tour or pick up their MP3 audio tour.
- Drive 45 minutes up to Hartford.
- Depending on your literary taste, you could visit either the Mark Twain House and Museum or the Harriet Beecher Stowe Center.
- Drive up north back into Massachusetts for about 1h40m where you start looking for fall foliage in earnest.
- Stop over in Stockbridge for a late lunch.
- Arrive at the Norman Rockwell Museum before 3pm to enjoy the fascinating exhibit of his amazing works that reflected an America of a bygone era. Don’t miss going out back to the replica of Mr. Rockwell’s studio.
- Drive back to Stockbridge’s Main Street. Walk around and find yourself in the middle of a Norman Rockwell painting. Stop in at the general supply store for candy and other knick knacks. Have dinner at the historic Red Lion Inn.
- Check in at your bed and breakfast in the Stockbridge area or head up another 15 miles north into Pittsfield and stay with Billy and Waterfall in their cozy home that they share with a sweet dog named Sequoia and a boss cat named Robert.
- Take in the New England morning over an breakfast before driving up 5 miles to The Mount. This is the home of Pulitzer Prize-winning writer Edith Wharton who wrote The House of Mirth and The Age of Innocence.
- Stop by a local store or deli and order a picnic lunch to take with you.
- Start driving on the Mohawk Trail and make your way through 3-4 hours of driving in a sea of orange and gold foliage. There are several routes to take. We went with the route that took us from Pittsfield to Williamstown then east through the North Berkshires.
- Find a spot for lunch along the way. I suggest to find a picnic spot at the Mohawk Trail State Forest, right by a lovely stream under the cover of golden leaves.
Take in the beauty of the surroundings, take your time to stop and take photos. Be careful to park safely to the side.
Find charming small towns to stop in to stretch your legs, like Shelburne Falls.
- Head north on I-91 into Vermont (approx. 2h 15m).
- Check in at your accommodations for the night. I recommend trying out a farmstay with James and Laura in Northfield.
- Take James, your host, up on his offer to tour the farm where you’ll get to meet the animals including Prudence the Pig and Hazel the Cow. Return to your room for breakfast before heading out.
- Head up to Montpelier and drive around the streets of this beautiful city. Stop for pastries and on the road snacks at Birchgrove Baking.
- Get back on the interstate. Depending on the season and the weather, the trees here may be bordering on brown or just about ready to fall off the branches.
- As you contemplate the coming of winter up in this northern part of New England, perk up your spirits at your next stop: the Ben and Jerry’s Factory. Join the 30 minute guided tour that includes a free sample.
- Get back in the car and head up the road for a couple of food stops. Go in for a sampling of scrumptious cheese at the Cabot’s Annex Store. Stop at Cold Hollow Cider Mill for their apple cider doughnuts and apple cider drink.
- With your eyes and bellies satisfied, buckle down for the easy 3-hour drive back to Boston.
- Check in at your Airbnb accommodation. I recommend Christian’s place, a spacious loft in a great central location that’s close to the downtown area and the airport.
- If you still have energy, head out for your last New England dinner. If you want to stay in the Chelsea area, Floramo’s is an Italian family style restaurant that’s an institution.
- Depending on what time your flight leaves, you may have some time to check out Boston’s landmarks. If you’re an art lover, the Museum of Fine Arts is a great visit. It you’re a sports fan, pay a visit to Fenway Park and do a tour of the home of the Red Sox. If you’re a history nerd, walk the Freedom Trail and learn about the American Revolution. You could go on your own or go with a guided tour.
This trip will give you a taste of New England’s charm. There’s so many other places to discover in this region all year round: there’s summer in Nantucket, winter skiing in Vermont and maple sugaring in the early spring. in New Hamsphire, among other trip ideas.