10 Places to Celebrate Fall in New England

See recent posts by Melissa Kravitz

Fall can be magical in many places, but it's especially charming in New England. The trees turn a fiery array of reds, oranges, and yellows, the grass smells fresh, and the coastal breeze feels calming. Beyond that, several New England towns celebrate autumn with festivals, food, fairs, and other seasonal events, too. Here, we compiled a list of the top spots to ring in the season.

1. Nantucket, Massachusetts

Nantucket may be known as a beach town, but visiting after peak season is a wise move. Not only is the isolated island calm and quiet during the fall, but the scenery is gorgeous as well. The crash of the ocean waves is just as mesmerizing even if it’s not warm enough to swim in. Local businesses, which lack the crowds come autumn, stay open. Visit September 26 through October 6 for Nantucket Restaurant Week. Those in the mood for seasonal eats should also plan a trip on October 8 for the annual Cranberry Festival, which celebrates Nantucket’s cranberry harvesting history as well as its two remaining organic cranberry bogs. 

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2. Berkshires, Massachusetts

The bucolic western Massachusetts destination, which was once a retreat for well-to-do Americans, offers plenty of quintessential fall activities. Indulge in apple picking and cider tasting at Hilltop Orchards, embark on a hike to Mount Greylock (the highest post in Massachusetts) for plenty of leaf-peeping opportunities, or take a narrated tour of the fall foliage on a train ride that’s operated by the Scenic Railway Museum. If you happen to be in town on October 8 and 9, stop by the Berkshire Botanical Garden Harvest Festival for food, local craft vendors, a farmers market, and more.

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3. New London, Connecticut


Founded in 1646, New London is rich with culture, historical sites, and majestic waterfront views. Visit this fall for the fourth annual Connecticut Maritime Heritage Festival, which sails into town the weekend of September 9 and features navy ships, schooners, whaleboat races, the Great New London Chowder Challenge, and more. Those who are in it for the food should visit on October 12, when the annual Fall Food Stroll offers dishes from nearly 50 local restaurants and specialty shops. Throughout leaf-peeping season, New London Landmarks will also host historical walks, where guests can explore the town’s architecture.

4. Newport, Rhode Island

Visiting mansions and exquisite waterfront properties in Newport is not a bad way to spend a fall day. Or many fall days. Endless cultural events and tours will keep travelers occupied. Or, enjoy a walkthrough of the iconic historical mansions yourself. Food and wine lovers should book a trip the weekend of September 22, when Jacques Pepin and other famous chefs are in town for the Wine & Food Festival.

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5. Uncasville, Connecticut

If being outdoors isn’t your thing, head to Uncasville, where the Mohegan Sun casino is the main attraction. Visit September 3 and 4 for the New England Food Truck Festival held at the property. Or, book a trip any weekend throughout the season to see concerts, comedians, and more. The weekend of October 14 marks Mohegan Sun’s 20th anniversary and a big blowout, including a performance by Fergie, is scheduled. 

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6. Montpelier, Vermont


Montpelier, Vermont‘s capital city, is part metropolis and part small town with plenty to do and see in the fall months. For starters, there are many hiking spots and scenic lookouts. And because this is Vermont, make sure to get your fill of local maple syrup. Morse Farm Maple Sugarworks is a great place to stock up on sticky sweets. For a unique fall experience, visit on October 1 and 2 for the Fall Fiber Festival, which features sheep dog trials, hands-on workshops, fiber and crafts vendors, a fleece sale, and above all, a picture-perfect autumnal landscape.

7. Warwick, Rhode Island


Warwick, Providence‘s cuter next door neighbor, was practically built as an ode to fall weather. Thirty-nine miles of exquisite coastline and an unprecedented view of Narragansett Bay make the town an ideal place to relax and soak up all the fall colors and breeze — perhaps with a good book in hand. Nearby, Johnson & Wales’ prized Culinary Arts Museum is worth a visit, too.

8. Portsmouth, New Hamphire


Culture, outdoor activities, and history all collide in Portsmouth. Countless breweries and wineries (some doling out seriously creative fruit-based vinos) might just put your California wine trip on hold. Plenty of golf courses also make this a relaxing destination for those who want to spend the day playing a round. Then, wander through one of the many parks and gardens before making your way to downtown Portsmouth to shop and eat. In addition, fall brings historic walking tours, farmers markets, and other special events like a craft festival, beer and chili festival, live music, and more. 

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9. Westport, Connecticut


Another coastal Connecticut town worth checking out come mid-September is Westport. Seafood enthusiasts should stop in town on October 2 for the annual New England Chowdafest, where regional restaurants compete for the best soup. With over 40 chowders to taste, you’ll leave feeling utterly satisfied. When you’re not gorging on chowder, enjoy an autumnal walk on the beach, stroll through Sherwood Island State Park, or take advantage of suburban amenities like a spa massage or SoulCycle class. 

10. Portland, Maine

Photo courtesy of Flickr/Jeff Gunn

Photo courtesy of Flickr/Jeff Gunn

Spend a weekend in Portland, Maine, soaking up all the season has to offer. Fuel up at one of the many tasty restaurants in town, then digest while marveling at the fall leaves. There’s even a site that tracks the foliage, so you know exactly what colors and sights you’ll see in each spot. Plan your adventures accordingly. For a break from all the foliage selfies, make a trip to the Portland Museum of Art or Portland Head Light, which is a historic lighthouse.

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