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.

One of our favorite ways to experience this magical time of year 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 colors and create brilliant landscapes of yellow, orange, and red. 

Peak fall foliage generally takes place between the last weekend of September and Columbus Day. For specific information on locations and the changing of the colors check out foliage trackers like ExploreFall.com.

5 Day New England Fall Road Trip  

With Logan International Airport Boston being a big international hub airport, we have designed our New England road trip itinerary with this starting point. Next, you’ll head 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. 

You can complete the drive from Bar Harbor back to Boston following this itinerary.

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. 

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. 

Stay overnight in Cape Cod – search suggestions here!

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.

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.

The Berkshires are known for their excellent Farm-to-Table culture. They have 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.

Staying overnight we recommend Stockbridge – search suggestions here!

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

If you have a little longer in the state, Massachusetts also has a number of incredible scenic drives, including the Mohawk Trail in the Berkshires youcould add to this itinerary, time permitting. 

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. 

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. 

Best places to stay in Burlington – search suggestions here!

Stowe, Vermont, is another 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. With extra time in your itinerary, we’d suggest staying an additional day in the area and heading up the Gondola SkyRide at Stowe Mountain Resort.

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.

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 a bucket list item and a must on any fall road trip itinerary. Besides the gorgeous fall colors, visiting Acadia in the fall means fewer crowds but colder temperatures.  

Many come to Acadia to hike the picturesque terrain but there are plenty of scenic driving routes to enjoy, 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 New England fall road trip activity that is permitted until late October. Vehicle reservations are required to drive to Cadillac Summit, so ensure you’ve reserved this journey in advance (30% of reservations go on sale 90 days in advance, the remaining reservations open 2 days in advance).

If the timing aligns, the Acadia Night Sky Festival and Acadia Oktoberfest are two great things to add to your New England fall road trip itinerary. 

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!

Best places to stay in Bar Habor – search suggestions here!

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

Consider driving along the Atlantic Coast to Boston when heading south from Acadia National Park. You’ll love 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, plus a stop at Take Flight Aerial Adventure Park is bound to be a must for the kids.

With an extra day or 2 available, don’t rush the journey back. Instead, follow our coastal itinerary from 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:
Individual states post their own yearly foliage maps like New Hampshire, Maine and Vermont
The Farmers Almanac uses historical data to predict the foliage schedule 
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 accommodation well in advance, particularly on weekends. 
Always stay up to date on weather and road conditions as things can rapidly change; New England 511 is an excellent resource to keep saved on your phone as it covers road conditions for the entire region. 
Find more inspiration here for fall getaways on the East Coast – plus don’t forget you can head a little further north and enjoy the best of fall in southern Canada, too.