New England in the Fall: A Guide to Seasonal Festivals and Events

Connecticut has hundreds of years of history behind it. At the Connecticut Maritime Heritage Festival in New London in early September, learn about the state’s storied, centuries-long connection to the sea. Get a glimpse of historic ships, watch maritime skills demonstrations, listen to live music, and enjoy a rum tasting, just to start. While history is a huge draw in Connecticut, The Constitution State has developed modern cultural ties as well. At the Soundside Music Festival in Bridgeport in late September, you can listen to top artists from every genre, including rock, folk, indie and alternative. At the Garlic & Harvest Festival in Bethlehem in mid-October, dive into this aromatic bulb with a series of garlic-focused experiences. Watch garlic cooking demonstrations, learn how to grow garlic at home, and try garlic-infused treats – like the incredible garlic ice cream!

Venture to Maine for fall events filled with local creations and all-around good vibes. In the little town of Unity, experience the agricultural celebration that is the Common Ground Country Fair. Organized by the Maine Organic Farmers and Gardeners Association, this September event showcases organic agriculture, rural living, sustainable practices and local purveyors. Continue the down-to-earth vibes with a visit to the Freeport Fall Festival. Held on the campus of famed outfitter L.L. Bean, this three-day early October festival features many of the coolest New England artists, makers and local food producers. Mid-October welcomes Maine’s delightful Damariscotta Pumpkinfest & Regatta. See massive artist-decorated pumpkins lining the streets, cheer for competitors in the pumpkin regatta (as in using giant pumpkins as boats), watch the pumpkin parade and delight in the pumpkin dessert contest. It’s enough to satisfy even the biggest fall fanatic.

Fall events in Massachusetts range from harvest celebrations to spooky affairs. If you’re into classic fairs and carnivals, The Big E in West Springfield is for you. Rides, beer gardens, farmers markets and live music are just the beginning. If ghouls and ghosts are more your style, Salem Haunted Happenings should be at the top of your list. Touted as the world’s largest celebration of Halloween, this month-long phenomenon in “The City of Witches” includes an array of parties, parades, markets and tours. If your version of fall is apple cider and apple pie, look no further than AppleFest at Wachusett Mountain. Celebrating all things apples, this mid-October festival features apple-themed treats, local beer, live music and SkyRides over the beautiful fall foliage.

New Hampshire might lay claim to the most unique fall event in New England with its Fairy House Tour in Portsmouth. Every third week of September, hundreds of magical fairy houses pop up across town – from the Strawbery Banke Museum and Governor John Langdon House to Prescott Park and the Gundalow waterfront. To celebrate this extra sprinkling of pixie dust, the town puts on fairy-inspired performances and parades, transforming into a whimsical wonderland for the weekend. New Hampshire’s fall fun doesn’t end there! Visit in mid-October for two more noteworthy events. Take part in White Mountain Oktoberfest in Lincoln by devouring delicious German beer and food among the colorful leaves at Loon Mountain Ski Resort. Head north to the Warner Fall Foliage Festival, where leaf-peeping meets an array of family fun. Taking place for more than 75 years, this beloved event features crafts, carnival rides and food vendors.

Despite being the smallest U.S. state, Rhode Island packs a lot of fall fun within its borders. Held in Providence, WaterFire is arguably the most famous event in The Ocean State. Starting on select nights in the summer through November, WaterFire is the lighting of 100 bonfires floating on the three rivers of the city accompanied by curated music and street performers. Another cultural centerpiece takes place the third weekend of September: The Newport Mansions Wine & Food Festival seamlessly blends cuisine, luxury and history. Buy tickets in advance for this intimate tasting experience at Rosecliff, one of Newport’s stunning Gilded Age mansions. On the opposite end of the spectrum, kick back at the casual Atlantis Rising event in Charleston. This mid-October sand sculpting competition draws sand artists from around the world. Stroll along the beach and admire the meticulously crafted sculptures all tailored to a particular theme each year. Live music, food vendors and a kid-friendly pirate school round out the event.

Vermont in the fall is a foodie haven. The Vermont Wine & Harvest Festival in Wilmington brings together vintners, brewers, cider-makers and distillers, as well as artisans and musicians, for days of deliciousness and creativity. An added bonus: The fall foliage of Mount Snow is the backdrop to this September event. Also in September, head off-the-beaten-path for the charming Peru Fair. Held in a town of the same name, this old-fashioned country fair boasts all sorts of vintage fun. Listen to old-timey live music, get the kids’ faces painted, watch magicians defy the laws of science, and pick up a few Vermont-made crafts. Don’t miss out on the crowd-favorite pig roast. For a culinary celebration of a more unique variety, head to Wardsboro, where the Gilfeather Turnip Festival is held every October. Centered around Vermont’s state vegetable, this event shows off the Gilfeather turnip in all its forms – from turnip soup to turnip baked goods. Plus, you can grab some turnips or turnip seeds to take with you, along with some locally made crafts.