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Essential New England Fall Festivals for the Whole Family

Fall fair and festival season is upon us in New England. There’s no better region of the country to celebrate the bounty of autumn, and there are plenty of places to find pumpkins, libations, and fantastic food. We’ve compiled a list of some of the premiere fall festivals so you can start planning your New England getaway.


credit: Maine Office of Tourism

Fall Festivals in Maine

Maine is chock full of good festival opportunities. Consider planning a Maine vacation in late October during the annual OgunquitFest, which includes activities like a scarecrow competition, fall story hour for kids, and a high heel race around Perkin’s Cove. Acadia’s Oktoberfest, usually a bit earlier in October, is another great festival full of beer-centric activities — try the Beerless Pong Tournament, the Stein Hoisting Contest, or Torpedo Keg Toss. HarvestFest in York, Maine, is a bit more kid-friendly with face painting, wagon rides, and alpaca visiting hours. Expect live entertainment, great food, and craftspeople to keep the streets lively.

Fall Festivals in New Hampshire

139 years of agricultural history make New Hampshire’s Deerfield Fair a uniquely fun stop for families. Here, the 4-H awards final prizes for livestock, baked goods, and more. Family events include puppet shows, demonstrations by Mad Science Scientists, a Pig Scramble, alpaca shows, and of course, live music to weave the whole weekend together. There’s no shortage of things to do and places to stay in New Hampshire.

Rhode Island Fall Festivals

Find your way to Smith’s Castle for the Smith’s Castle Harvest Festival in late September for a sure-fire good time. Stay in Rhode Island and meet local historians like Tim Cranston and Bob Geake, and friendly alpacas and horses from the local area. Other activities include wool spinning lessons, tips on preserving, and a pie eating contest.

Connecticut Fall Festivals

Stamford Museum’s Harvest Festival happening in October makes our essential fall festivals list with activities like apple cider pressing, an apple slingshot, a costume parade, face painting, live music, and more. Explore Connecticut lodging options and time your trip with Connecticut’s foliage, which hits peak a little later in the season than in its neighboring states to the north.

Massachusetts Fall Festivals

credit: Massachusetts Office of Travel & Tourism
credit: Massachusetts Office of Travel & Tourism

The Martha’s Vineyard Food and Wine Festival is unique in its individually ticketed format: choose between Signature Events, Small Batch Experiences, Dinner Pop Ups, and the Winemaker Cellar Series and pay only for events you’d like to attend. Meet the local culinary talent during your stay on Martha’s Vineyard, and the farmers, fishermen, oyster producers, and artisans they work with — along with guest chefs and vintners from around the world. If you’re bringing the kids, the Berkshire Botanical Garden Harvest Festival may be more your style. Kids will love the bounce house, sword performances, sand art, and friendly hosts like Polly and Molly the goats! These fall festivals are proof that Massachusetts vacations aren’t just for beach season.

Vermont Fall Festivals

Harpoon Octoberfest is just what you would expect from a festival at a brewery: continual live oompah music, chicken dancing, cake eating, bratwurst, and of course, barrels upon barrels of freshly brewed Harpoon beer. If you prefer grapes over hops, we recommend the Vermont Wine and Harvest Festival. Taste your way around Mount Snow, sampling dozens of Vermont’s finest wines, spirits, cheeses and farm-fresh products. Vermont accommodations range from classic inns and bed and breakfasts to full-scale resorts. If your fall priorities include pumpkins and apples, crisp fresh air and vibrant leaves, these New England fall festivals should fit perfectly into your schedule. Wishing you and your family a fantastic foliage season from New England.

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