Fabulous 5 Day New England Fall Road Trip

There’s nothing quite like fall in New England. As the summer sun begins to fade, we begin to crave the feeling of crisp fall air, the tastes of freshly harvested apples, cranberries and pumpkins, and, of course, the beautiful fall foliage.

The best way to experience this magical time is by taking a New England road trip

Typically, fall in New England runs from September 1st through late October. It’s during this time that you’ll find a number of family-friendly festivals celebrating the sights, sounds, and tastes of the season. It’s also when leaves change their colors and create brilliant landscapes of yellow, orange, and red. 

Peak fall foliage generally takes place between the 1st of October and Columbus Day. For specific information on locations and the changing of the colors check out foliage trackers like those of Vermont, Maine and New Hampshire

5 Day New England Fall Road Trip  

There are a number of different fall road trips in New England to choose from. Here, we’ve designed one that’s ideal for a long weekend. Depending on your starting point, you can arrange your New England fall road trip itinerary to suit your needs. 

If you’re flying into the area, Boston is a good starting point with Logan International Airport. The fall road trip itinerary we’ve put together here does just that. It begins in Boston, then heads west to the Berkshires, up north through Vermont, and then east to the Acadia on the coast by way of the White Mountains of New Hampshire. 

Since this trip is all about seeing the beauty of fall in New England, remember that leaves change earlier in the season, the further north and inland you are. So, if you’re visiting later in the fall, the suggestion would be to start in the north and work your way south. 

Day 1: Boston & Cape Cod, Massachusetts

There’s no better way to start an epic New England Road Trip than with a day in the great city of Boston. 

USA New England Fall Road Trip - Cape Cod

Fall is the perfect time of year to explore all the historic sites of this great city. Walk the Freedom Trail, stroll through Boston Commons, and check out the big ships in the harbor. If the weather is a little bit iffy, kids will love to visit the New England Aquarium and see all the underwater creatures. 

Boston is also a great home base to explore the surrounding area. Salem, Massachusetts, is a mere 30 minutes from downtown and has so much fun during the Halloween season. 

Driving south from the city, it’s easy to spend a day exploring Cape Cod as the fall colors change in the season. The whole family will love exploring the towns on the cape and walking along the sandy beaches. Don’t miss a visit to the Whydah Pirate Museum in West Yarmouth.

Fall on the Cape is tons of fun, with the Harwich Cranberry & Arts Festival in September and the Yarmouth Seaside Festival in October. Both are tons of fun for the family, with music, vendors, and fireworks. 

Day 2: Berkshires, Massachusetts

In less than a three-hour drive west on I-90 it’s on to the second leg of this New England road trip, The Berkshires. Set in Western Massachusetts, this landscape is an escape into nature any time of year. But fall foliage transforms the area to be even more breathtaking.

USA New England Fall Road Trip - Berkshires

Any New England road trip should plan for at least a day in the Berkshires. Here, it’s easy to fill your fall road trip itinerary with outdoor activities like hiking, biking, and even horseback riding.

In the fall, the whole family will love picking apples or pumpkins and sipping cider at places like Bartlett’s or Furnace Brook Winery at Hilltop Orchards. The Naumkeag Pumpkin Show in Stockbridge is a favorite with families throughout October.

Known for its excellent Farm-to-Table culture, the Berkshires has wonderful restaurants and farmers’ markets. Towns like Pittsfield, Lenox, and Williamstown have excellent markets to explore through October. 

For outdoor adventures like ziplining and alpine sliding, head to Jiminy Peak or Berkshire Eastern Mountain Resort.

Pro Tip: The Berkshires are the perfect place to camp. With dozens in the area, it’s easy to find the one for you, including RV hookups like at Fernwood Forest Campground. 

Pro Tip: Massachusetts has a number of incredible scenic drives, including the Mohawk Trail in the Berkshires. 

Day 3: Burlington, Vermont

Nothing quite compares to Vermont in the fall. The Green Mountains are picturesque as they change colors from green to brown, orange, and yellow. There’s no better way to enjoy the season than taking a New England fall road trip to Burlington with your family. 

USA New England Fall Road Trip - Green Mountains

The drive from the Berkshires to Burlington takes only about three and a half hours without stopping. But instead of rushing along, we recommend stopping off at Woodstock (VT, not NY) and Montpelier. Both are quintessential Vermont towns and are postcard-perfect in the fall.

An excellent family activity is visiting the Ben & Jerry’s ice cream factory, just a short distance from Burlington. No matter your age, you’ll love learning about Ben and Jerry’s journey to becoming the kings of ice cream.

In Burlington, don’t miss exploring Church Street Marketplace, walking along the shore of Lake Champlain on the Greenway, or enjoying any of the great restaurants in town. 

The Lake Champlain Byway is one of the most scenic drives in Vermont and runs through Burlington. Check out this and other scenic drives in the state. 

Pro Tip: On the drive between Berkshires and Burlington, take a detour to check out the Vermont Wine and Harvest Festival in West Dover. 

Pro Tip: Stowe, Vermont, is a favorite place among leaf-peepers, and it’s less than an hour from Burlington, making for a convenient detour on your New England fall road trip. 

Day 4: White Mountains, New Hampshire

Heading east from Burlington, it’s on to the White Mountains of New Hampshire. It’s a gorgeous landscape that is best experienced during the fall foliage. In fact, it’s one of the best places to spend fall in New England. 

USA New England Fall Road Trip - White Mountains

Anyone will tell you the best views are from the top of the mountains in New Hampshire. In the White Mountains, there are so many ways to get there. You can ride a gondola at Loon Mountain, hop on a cable car at Cannon Mountain, zip through the trees at Gunstock Mountain, or simply hike to the top of one like Mount Lafayette. They’re all great places to visit in New Hampshire in the fall.

One of the most memorable activities to do as a family in New Hampshire is to climb Mount Washington on the Auto Road. As the tallest peak in the Northeast, it’s one of the best places to visit in New Hampshire in the fall. 

New Hampshire has some of the most beautiful scenic driving in New England. Definitely check out Kancamagus Highway (Route 112) and five other travel-worthy drives in the state.  

Pro Tip: Get the Mt. Washington App to get up-to-date info and listen to audio tours on your climb. 

Pro Tip: There are vehicle restrictions for the Auto Road up to Mount Washington (sorry, no RVs). Check your specs on the websites before starting out on some of the hardest driving in New England.  

Day 5: Acadia National Park & Bar Harbor, Maine

On the final leg of this splendid New England fall road trip, set your sights on Acadia National Park and Bar Harbor, Maine. 

Coming from New Hampshire, the drive should take just under four hours. If you’re not in a huge rush, consider going by way of Rangeley Lakes National Scenic Byway. It’s one of the best parts of driving in New England.

USA New England Fall Road Trip - Acadia National Park

Once you arrive, you’ll understand why Acadia National Park is one of the most visited parks in the country. Visiting this beautiful landscape is definitely a bucket list item and a must on any fall road trip itinerary. Besides the beautiful fall colors, visiting Acadia in the fall means fewer crowds but colder temperatures.  

Many come to Acadia to hike the picturesque terrain. Another great idea is to drive it, too. The Acadia Byway (Route 3) will take you onto Mt. Desert Island around the park and to Bar Harbor. 

Driving up Cadillac Mountain is a favorite thing to do on a New England fall road trip and is permitted until late October. Vehicle reservations are required to drive to Cadillac Summit. So, make sure to reserve yours in advance.

Two great things to add to your New England fall road trip itinerary are the Acadia Night Sky Festival and Acadia Oktoberfest

The historic coastal town of Bar Harbor is the perfect place to stay when visiting Acadia. There are plenty of places to stay, small shops and quaint restaurants. As the season winds down, so does the town. So, it’s best to visit in September and October. 

Pro Tip: Acadia National Park requires an Entrance Pass. Get yours in advance on the NPS website, or if you have a 4th grader in the family, you could be eligible for free entry!

Pro Tip: If you love the scenery in Maine, why not go further on these 7 incredible scenic drives in the state?  

Heading back south from Acadia National Park, consider driving along the Atlantic Coast to Boston. You’ll love all of the quaint seaside towns and the view from the road. Make sure to stop off at the historic town of Portsmouth. It’s one of the best places to visit New Hampshire in the fall – you could follow this coastal itinerary Boston to Bar Harbor in reverse. 

More Tips For A 5 Day New England Fall Road Tripping 

  • Knowing the fall foliage schedule is essential for the perfect New England road trip. The following sites have some of the best info:
  • Peak fall foliage happens earlier in the north and inland. So, it’s ideal to visit places like Burlington, Vermont in September.
  • Visiting New England during the fall is super popular. So, make sure to arrange accommodations and book reservations in advance. 
  • Always stay up to date on weather and road conditions. Conveniently, New England 511 has current road conditions for the entire region. 
  • Find more inspiration here for fall getaways on the East Coast.
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