As the first day of autumn arrives on September 22, 2025, New England's landscapes transform into a breathtaking canvas of fiery reds, vibrant oranges, and golden yellows—often evoking the whimsical hues of cotton candy skies at sunset. This season marks the perfect time to embrace the region's rich tradition of fall fairs and festivals, where the harvest bounty comes alive through family-friendly events, delicious treats, live entertainment, and community spirit. From classic agricultural fairs with livestock shows and midway rides to pumpkin extravaganzas and foliage celebrations, New England's autumn calendar is packed with opportunities to create lasting memories. Whether you're a local or a visitor, these events highlight the area's agricultural heritage, artisanal crafts, and seasonal flavors like apple cider, pumpkin pie, and fried dough. Below, we explore some of the top fall fairs and festivals kicking off around September 22 and extending into October, drawing from the latest 2025 schedules across Connecticut, Massachusetts, New Hampshire, Rhode Island, Vermont, and Maine.
Iconic Multi-State and Large-Scale Fairs
The Eastern States Exposition, affectionately known as The Big E, is one of New England's crown jewels and a must-visit for anyone seeking an all-encompassing fall experience. Running from September 12–28, 2025, in West Springfield, Massachusetts, this massive 17-day event draws over 1.5 million attendees annually. It celebrates all six New England states through themed buildings along the Avenue of States, featuring historical exhibits, live demonstrations, and state-specific foods like Rhode Island clam chowder or Vermont maple treats. Highlights include agricultural displays with prize-winning animals, thrilling midway rides, parades, top-name concerts (past performers have included country stars and rock bands), and indulgent fair fare such as deep-fried Oreos, cider slushies, and butter sculptures. Admission is around $15–20 per day, with free parking shuttles available—perfect for families looking to immerse themselves in regional pride just as fall foliage peaks.
For a historic touch, the Topsfield Fair in Topsfield, Massachusetts (October 3–13, 2025), stands out as America's oldest continuously running agricultural fair since 1812. Expect classic fair vibes with ox-pulling contests, giant pumpkin weigh-offs, livestock judging, and a massive food court boasting everything from lobster rolls to whoopie pies. The fair's rural charm, combined with modern amusements like a full carnival midway, makes it ideal for all ages, especially with the surrounding Essex County foliage providing a stunning backdrop.
Connecticut: Country Fairs and Harvest Traditions
Connecticut's fairs emphasize its farming roots, with several events overlapping the autumn equinox. The Durham Fair (September 25–28, 2025), in Durham, is the state's largest agricultural fair, founded in 1916. Spanning four days on a historic site, it features three livestock barns, tractor pulls, baking and canning exhibits, horticulture displays, and photography contests alongside midway games and rides. Fairgoers can indulge in homemade pies, corn on the cob, and apple cider while enjoying live music and craft vendors. It's a quintessential New England harvest celebration, drawing over 150,000 visitors. Nearby, the Berlin Fair (September 11–14, 2025, but extending vibes into late September) offers a more intimate experience with its origins as a 1882 Harvest Festival, including animal exhibits, food trucks, and aerialist performances.
Heading into October, the Harwinton Fair (October 3–5, 2025) delivers old-fashioned fun along the scenic Farmington River, complete with wood-chopping events, vendors, midway rides, and live music. For a harvest twist, check out the Southington Apple Harvest Festival (late September into early October), which celebrates the state's orchards with apple-picking, cider pressing, and family activities.
Massachusetts: Foliage-Focused Fun and Renaissance Revelry
Massachusetts shines with events that blend fall's natural beauty with festive energy. The Johnny Appleseed Festival in Leominster (September 20–21, 2025) honors the legendary figure with over 200 vendor booths, live music, kids' games, and apple-themed desserts—think caramel apples and cider donuts under cotton candy skies. It's a free, community-driven event perfect for the equinox weekend.
For ongoing autumn magic, King Richard's Faire in Carver (weekends from August 30–October 19, 2025) offers a Renaissance twist on fall festivities. Set on 80 acres of enchanted forest, this immersive experience includes jousting tournaments, artisan crafts, turkey legs, and interactive shows with jesters and magicians. Tickets start at $35, providing a unique way to extend the fair season into mid-autumn.
Don't miss the Harvest Moon Festival in Onset (early October), featuring an antique car show, petting zoo, food trucks, live music, and a fireworks finale over Buzzards Bay. The Spencer Fair (mid-September) rounds out the state's offerings with carnival rides, animal exhibits, and classic fair food.
New Hampshire: Agricultural Gems and Foliage Festivals
New Hampshire's fairs capture the Granite State's rugged charm. The Deerfield Fair (September 25–28, 2025), one of the region's oldest and largest agricultural events, spans 139 years of history at the fairgrounds in Deerfield. Expect endless food vendors, livestock barns, a large carnival midway, and four days of live entertainment, including fireworks and music. It's family-oriented with kids' rides and animal shows, set against emerging fall colors.
The NH Highland Games & Festival (September 19–21, 2025) at Loon Mountain in Lincoln kicks off the season with Scottish heritage celebrations: caber tossing, bagpipe bands, clan gatherings, and athletic competitions amid stunning White Mountain foliage. For October, the Milford Pumpkin Festival (October 10–12, 2025) transforms the town oval into a gourd wonderland with over 5,000 carved pumpkins, live music, food vendors, and a pie-eating contest. The Warner Fall Foliage Festival (October 10–12, 2025) features parades, craft fairs, and apple-themed eats in a foliage hotspot.
Rhode Island, Vermont, and Maine: Coastal and Mountain Celebrations
In Rhode Island, the Bowen’s Wharf Seafood Festival (October 18–19, 2025) in Newport brings coastal flair with fresh seafood tastings, live music, and waterfront views—ideal for pairing with a drive through fall foliage. Earlier, the Newport Mansions Wine & Food Festival (September 19–22, 2025) offers gourmet pairings and tastings in historic settings, aligning perfectly with the autumn start.
Vermont's 64th Annual Art in the Park Fall Foliage Festival (October 11–12, 2025) in Rutland showcases juried artists, craftspeople, and specialty foods amid peak leaf-peeping season. For a car enthusiast twist, the Middlebury Car Show & Fall Festival (early October) includes 75 classic vehicles, food trucks, vendors, music, and kids' activities on Main Street.
Maine rounds out the region with OgunquitFest (late October), featuring scarecrow contests, kids' story hours, and a high-heel race, plus harvest-themed crafts. The HarvestFest in York (early October) offers face painting, wagon rides, alpaca visits, live entertainment, and local foods. Up north, Sunday River's Fall Fest celebrates foliage with events like the North American Wife Carrying Championship, New England Cornhole Championship, and craft fairs.
Tips for Enjoying New England's Fall Fairs and Festivals
As you plan your visits starting September 22, 2025, consider the weather—pack layers for crisp evenings under those cotton candy skies. Many events are outdoors, so check for rain dates, and arrive early for parking. Admission varies (free to $20+), and some require advance tickets for concerts or special exhibits. Pair your fair day with leaf-peeping drives, as New England's foliage peaks from late September through mid-October. For families, look for kid-friendly perks like petting zoos and hayrides; foodies will love the regional specialties. Always verify details on official websites, as schedules can shift.
New England's fall fairs and festivals aren't just events—they're a heartfelt nod to the season's magic, where community, nature, and nostalgia intertwine. Whether you're munching on fair treats or admiring the harvest displays, this autumn promises unforgettable adventures. Happy fall!