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4 New England Fall Road Trip Ideas

Are you looking for some New England road trip ideas?  It’s now fall, and despite the fact that we were able to spend the weekend on the beach last weekend, it’s really a great time for some fabulous fall road trips. 

Fall is a great time to travel on a New England road trip with your family, because the weather is usually good for travel, and the weather is still good for some outdoor activities. Of course, there is also that gorgeous world-famous New England fall foliage, so it’s the perfect time for a leap peeping trip.

In general, you can really look at two different aspects of the fall for your New England road trip. The beginning of fall can almost feel like summer, so it’s a good time to take advantage of the warm temperatures and smaller crowds. Just do some research in advance because some restaurants and attractions may have seasonal closings after the summer.

October, especially late October, is peak fall foliage season in New England. Of course, the season varies by year, so you’ll want to do some seasonal research if you are hoping to see the leaves changing color.

Regardless of when in the fall you are traveling, or how much time you have, there are lots of great options for New England fall road trips – here are my favorites.

Note: some of the hotels mentioned were visited at no cost for purposes, and some links are affiliate links. A purchase/click through one of these links may result in a commission paid to us at no additional cost to you. All opinions are my own.

New England Road Trip Ideas for the Fall

Hilton Garden Inn Freeport

Freeport, Maine

A few years ago, we road tripped up to Freeport, Maine for a weekend away. We were able to attend a fall festival at Wolfe’s Neck Farm, shopped at the outlets (including the LL Bean flagship store), and swam in our hotel’s indoor pool.  It was a great getaway and the kids also had a wonderful time.

The coast of Maine would be a great road trip. If you start in Boston, you can drive up past Portsmouth, NH, Kittery Maine, and Portland, Maine. You could get some outlet shopping done in both Kittery and Freeport, and the late fall can be a great time to get started on Christmas shopping.

We also really love Ogunquit, Maine, which is located about 20 minutes north of Kittery. Ogunquit is a beach town, but it’s extremely popular in the summer. If you visit in the fall, you’ll be able to enjoy the shops and restaurants with less crowds.

During your road trip, be sure to get a famous lobster roll at one of the many road stands throughout the state. Bob’s Clam Shack in Kittery is one of my favorites.

See hotels in Freeport, Maine.

Nantucket, MA

Nantucket isn’t technically a road trip destination, since you’ll need to take the ferry to get there. But, it’s still a great fall destination within New England. Hotel rates are lower in the fall, and if you travel over Columbus Day weekend, you can enjoy the family-friendly Nantucket Cranberry Festival.

Like Cape Cod, Nantucket gets significantly less crowded in the late summer/early fall, but you can still have some great weather. It’s always a good idea to make your Nantucket ferry reservations in advance, because they do fill up – even when the crowds are smaller.

Depending on where you are staying, you probably won’t need your car – book a passenger ferry and skip the car ferry. Parking on the island can be challenging, so it’s best to walk everywhere. So, road trip to the ferry and leave your car in the lot to save money and hassle.

See hotel reviews in Nantucket here.

North Conway, NH

Story Land NH, one of the most popular theme parks in New England, is open through Columbus Day. New Hampshire is lovely in the fall, so hop in the car, and travel up to North Conway to enjoy the weekend away. There are lots of other things you can do while you are up there – even visit the North Conway outlet shops for some belated back-to-school shopping.

For a gorgeous New England fall road trip, consider driving from the Lincoln, NH (where you’ll find the Franconia Notch State Park) to North Conway on the Kancamagus Highway. This scenic byway, which goes through the White Mountain National Forest, is a stunning ride in any season. During foliage season, it’s the perfect drive to do some leaf-peeping.

New Hampshire is an especially popular fall foliage destination, so I’d recommend booking in advance and going on an off-peak time if possible. Holiday weekends can be especially busy and expensive.

See hotel reviews here.

Cape Cod, MA

Cape Cod, like Nantucket, is another destination that’s much more affordable in the fall than it is in the summer. It can also be a much more relaxing experience because there are so many less people.

Many hotels, like the Sea Crest Beach Hotel (where we’ve stayed in the fall a few times) offer indoor pools, so you can swim even if the weather doesn’t cooperate.

For a history road trip, start in Boston, (or more North, in Salem, MA) and head south towards the Cape. While you are in Boston, visit the Freedom Trail and other historic sites right in the city. Then stop in Plymouth on your way to the Cape to visit Plimoth Plantation.

While you may also consider visiting Plymouth Rock for the historic significance, I prefer Plimoth Plantation for the learning experience. Plymouth Rock is a bit disappointing because it’s so much smaller than you’d expect.

See hotels in Cape Cod here.

Although not included here, there are lots of other gorgeous destinations for a New England fall road trip. These include Newport, Rhode Island, Acadia National Park in Maine, the Mohawk Trail in Western Massachusetts (the first scenic road in New England), and Mount Washington, NH.

Related: Day Trips From Boston

Where will you be road tripping this fall?

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