41 New England Fall Fairs & Festivals

Autumn in New England is all about finding color—the stunning foliage variety, of course, but also the kind of local color you find at harvest celebrations. This is the season when visitors and locals alike converge on fairgrounds to see magnificent draft horses, eat fried dough, and stroll the midway. They also flock to town centers for fall festivals, to taste prize-winning apple pie and watch kids playing on the village green. More than anything, though, they go beyond leaf-peeping to embrace the autumn experience in all its many forms. Here are some classic New England fall fairs and festivals where you can do just that. 

41 New England Fall Fairs & Festivals

CONNECTICUT

Apple Harvest Festival,Southington. One weekend isn’t enough for this salute to fall’s favorite fruit. Southington’s lovely town green hosts the event featuring rides, a crafts show, music, and food, with apples making their appearance in pies, fritters, slushies, and by their own crisp, sweet selves. Evenings are capped with fireworks, and a parade along a one-mile route highlights the opening weekend. 9/30–10/2 and 10/7–10/9; southington.org

Berlin Fair,Berlin. This central Connecticut tradition has all the favorites: farm animals and fat pumpkins, carnival rides (including the famed Himalaya), and music ranging from big-name acts to local talent. But the standout is the amazing array of food, all prepared by church groups and charitable organizations. After wolfing down clam chowder, eggplant fries, and peach fritters, come back the next day for a “Veggie Power Blend Sandwich.” 9/15–9/18; ctberlinfair.com

Durham Fair,Durham.Connecticut’s largest agricultural fair combines the harvest season’s abundance of fruit and vegetables with livestock competitions, arts and crafts exhibits, live music, and of course plenty of food, games, and rides along the midway. There’s a monster truck rally and a lumberjack show (ax-throwing, anyone?). 9/22–9/25; durhamfair.com

Four Town Fair,Somers.Dating to 1830, Four Town is one of New England’s oldest harvest fairs. In addition to traditional livestock, garden produce, and crafts exhibits and competitions, things get lively with eating contests (pie, corn on the cob) and doodle bug pulls. What’s a doodle bug, you ask? It’s a small tractor, hand-assembled from old truck parts. 9/15–9/18; facebook.com/fourtownfair

Goshen Fair,Goshen. Tucked into northwest Connecticut’s scenic hill country, Goshen celebrates Labor Day—and the area’s farms and gardens—with a weekend’s worth of agricultural exhibits, livestock judging, and the midway traditions of rides and fair food. Enjoy old-time fiddling, magic shows, hay bale– and skillet-throwing contests, and (for the more sedentary) an apple fritter–eating competition. 9/3–9/5;goshenfair.org

Guilford Fair,Guilford. The Guilford folks take animal exhibits way beyond farm livestock, with an educational zoo show that features critters ranging from kangaroos to pythons. This is a fair with a circus built in (performances include trapeze and high-wire acts), but down-to-earth traditions such as tractor pulls are still part of the fun. Right on the fairgrounds is the Woodruff Barn Farm Museum, chock-full of antique farm machinery and other agricultural artifacts. 9/16–9/18;guilfordfair.org

Wolcott Country Fair,Wolcott. Wolcott’s big weekend packs what just might be Connecticut’s most eclectic assortment of fair spectacles, contests, and events, from Dock Diving Dogs to karate demonstrations to a pizza-eating competition to a “Forged in Fire” knife making exhibition. Not enough? Then head for the equestrian obstacle course, catch some live music, and see who takes the title of Little Miss Wolcott. 9/23–9/25;wolcottfair.com

Woodstock Fair,Woodstock. A Labor Day mainstay of Connecticut’s “Quiet Corner” for more than 160 years, the Woodstock Agricultural Society’s fair combines traditional displays of farm and garden bounty, sheep-shearing demonstrations and ox pulls, and a horse show with rides and music ranging from local to national acts. Fair food abounds—as does an unusual citrus twist on all the fun, in the form of grapefruit bowling. 9/2–9/5;woodstockfair.com

MAINE

Blue Hill Fair,Blue Hill. This “down to earth” fair was the model for the one in E.B. White’s Charlotte’s Web, and to this day, a special tent holds all the animals from the book (which was written in nearby Brooklin). The rides, farm exhibits, and fair foods that Charlotte and Wilbur’s human friends enjoyed are here, along with sheepdog trials that draw competitors from all over. 9/1–9/5;bluehillfair.com

Common Ground Country Fair,Unity. The Maine Organic Farmers and Gardeners Association puts a sustainability spin on its annual celebration of members’ produce, livestock, and crafts. Tasty homemade food, demonstrations of old-time agricultural techniques, a straight-from-the-farm fiber marketplace, animal exhibits, and a farmers’ market are just a few of the highlights. 9/23–9/25;mofga.org

Cumberland County Fair,Cumberland. Turning 150 this year, southern Maine’s biggest fall festival packs in events as diverse as truck and tractor pulls, a rodeo, a demolition derby, nightly fireworks, and 10 live-music acts spanning blues to bluegrass and everything in between. And who needs pies when there’s a burrito-eating contest? 9/25–10/1;cumberlandfair.com

Fall Foliage Festival,Boothbay. Boothbay’s fall event takes place on handsome four-acre town green, done up as a “vintage village” featuring art exhibits, food trucks, booths selling local crafts, live music, and a children’s corner. Take a ride on a steam-powered train at Boothbay Railway Village, and visit the adjacent antique car museum. 10/9–10/10;railwayvillage.org; boothbay.org

Farmington Fair,Farmington. Central Maine’s big September event delivers the expected—a lively midway, tractor and horse pulls, lots of good fair chow—plus events including harness racing, an ugly veggie contest, and a “Drag Your Neighbor” competition, where you can floor your ride without getting a speeding ticket. 9/18–9/24;farmingtonfairmaine.com

Fryeburg Fair,Fryeburg. Since its start in 1851, western Maine’s harvest fest has grown into an eight-day celebration of the region’s farms, gardens, foods, and crafts. Midway rides and oxen pulls, calf and pig “scrambles,” and an anvil-throwing contest vie for popularity with midway rides and a farm museum, and the Woodsmen’s Field Day draws loggers from across the U.S. to test their mettle. 10/2–10/9; fryeburgfair.org

Harmony Free Fair,Harmony. Yes, it’s free. And for a town with fewer than a thousand folks, Harmony stages a surprisingly big event. Along with local music acts and traditional agricultural and animal exhibits, the accent is on friendly competition, with tournaments in volleyball, cornhole, arm wrestling, horseshoes, skillet and hammer throwing, and even cribbage. And it all ends with a big Labor Day parade. 9/2–9/5;harmonyfreefair.weebly.com

New Portland Lions Fair,New Portland. Up near Skowhegan, far from the “old Portland,” the local Lions pair their midway, food booths, and agricultural attractions with plenty of lively competitions, such as wrestling matches, a demolition derby, and a kids’ “eel race,” done on hands and knees with participants holding on to their teammates’ ankles. 9/16–9/18;newportlandlionsfair.com

MASSACHUSETTS

Belchertown Fair,Belchertown.Hometown spirit sounds off when Saturday’s fair parade follows a concert by the local high school band. The fun starts Friday, when fall festival exhibits, farm animals, rides, and food combine with events including a K-9 demo and a baby contest, and a stilt-walking juggler strolls the grounds. Entertainment is free, including this year’s Fleetwood Mac tribute band. 9/23–9/25; belchertownfair.com

Eastern States Exposition,West Springfield. In New England, the “Big E” tops them all. It’s the third largest agricultural fair in the U.S., with a mind-boggling array of food (BBQ brisket sundae, anyone?), midway rides, big-name music acts, a farmers’ market, and those amazing butter sculptures. The horse, dog, and farm animal shows draw competitors from all over. 9/16–10/2;thebige.com

Franklin County Fair,Greenfield.The fair’s 173rd edition holds to tradition with an emphasis on livestock competitions: Draft horses, oxen, dairy cattle, sheep, and goats all vie for best-of-breed status. Hit the rides all day long with a one-price wristband, and enjoy local music acts, “Swifty Swine,” magic shows, and a demolition derby. 9/8–9/11;fcas.com

Spencer Fair,Spencer. This harvest celebration takes its agricultural exhibits beyond giant pumpkins and garden produce, to sunflowers and other field crops. There are antique tractors on display, pulling competitions involving everything from enormous oxen and draft horses down to lowly garden tractors, an amateur log-sawing contest, concerts, and rides including Air Force One, open to POTUS wannabes of all political persuasions. 9/2–9/5;spencerfair.org

Sterling Fair,Sterling.At New England’s largest free fair (rides do require tickets), there’s an antique engine and machine show, helicopter rides, and judging of crafts and goodies ranging from photography to chocolate chip cookies. This year’s event includes a Lego show, with kids up to age 17 bringing their creations to compete for awards. 9/8–9/11; sterlingfair.org

Three County Fair,Northampton. Since 1818, Hampshire, Franklin, and Hampden counties have been showcasing the bounty of the Pioneer Valley and western Massachusetts. Staying true to its mission of promoting “agricultural education and science,” the fair draws farmers sharing techniques and families viewing livestock and prize produce, while offering food and fun that the founders never imagined. (There were no demolition derbies in 1818!) 9/2–9/5;3countyfair.com

Topsfield Fair,Topsfield.America’s oldest continuously operating fair is the prime North Shore harvest season event. Enjoy rides that ramp up from “kiddie” to “thrill,” monster trucks, horse and oxen pulls, and the New England Rodeo, plus competitions that range a pumpkin weigh-in to fine art to canning to winemaking. Hungry? Try the Gobbler (“Thanksgiving dinner in a sandwich”) or maybe some deep-fried Kool-Aid. 9/30–10/10; topsfieldfair.org

NEW HAMPSHIRE

Apple Harvest Day,Dover. Dover’s one-day celebration of all things apple is held right downtown, with more than 60,000 people gathering along the banks of the Cochecho River for a family-focused event comprising a craft fair, five stages of live entertainment, 5K run, activities for kids … and, of course, an apple pie contest. 10/1; dovernh.org

Deerfield Fair,Deerfield. Harvest season between Concord and the coast is punctuated by one of New Hampshire’s biggest fairs, with all the favorite farm and garden exhibits, plus a pros-only excavator rodeo, puppet shows for kids, and the famed Flying Wallendas. Musical entertainment is eclectic, with bluegrass, rock, blues, reggae, and Irish traditional. 9/29–10/2;deerfieldfair.com

Granite State Fair,Rochester. The midway rides, livestock exhibits, and traditional fair food aren’t what sets this southern New Hampshire event apart, but rather the performances both weekends by the 100-year-old Circus Hollywood, as well as an unusual twist on that crowd-pleaser, the demolition derby. In addition to a showdown among cars, there’s a bus derby and a trailer derby (with predictable vehicular mayhem). 9/15–9/18 and 9/22–9/25;granitestatefair.com

Hillsborough County Agricultural Fair,New Boston. Just 16 miles west of Manchester but a world apart, Hillsborough County’s fairgrounds are the venue for one of New England’s oldest agricultural festivals. Expect all the classic attractions: farm animals for show and pulling contests, prize fruits and vegetables, midway rides, good things to eat, and a special emphasis on 4-H accomplishments, including dog training. 9/9–9/11; hcafair.org

Hopkinton State Fair,Hopkinton. Farming is the focus here, thanks to the Morrill Family Farm Museum and an array of modern agriculture and animal exhibits. Equines are front and center, from draft horses to miniatures, plus pony rides for kids. The Northeast Six Shooters dazzle with their horseback skills, using blanks to pop balloons from the saddle. A midway, petting zoo, and sugarhouse round out the fun. 9/1–9/5; hsfair.org

Lancaster Fair,Lancaster. The North Country’s biggest Labor Day weekend celebration spotlights local agricultural and craft traditions, along with special events such as Cruise Night, featuring ’50s cars and trucks; “Farmer for a Day,” for kids; sheepdog trials; pulling competitions; and a demolition derby. Midway rides are included with admission. 9/1–9/5; lancasterfair.com

Sandwich Fair,Sandwich. With a nod to New Hampshire’s lumberjack days, Sandwich’s fall festival includes log skidding with oxen. There’s also an antique auto parade, performances by the Granite State Disc Dogs, and a horseback gymkhana. Crafts? Expect plenty, at the hometown of the League of New Hampshire Craftsmen. 10/8–10/10; thesandwichfair.com

RHODE ISLAND

Autumnfest,Woonsocket. Rhode Island’s biggest fall festival is a Columbus Day weekend extravaganza featuring rides, a food court, continuous performances by local and top-name bands, comedians, crafts displays and marketplace, classic and muscle car shows, a wine garden—and on Monday, a Columbus Day parade. 10/7–10/10; autumnfest.org

Harvest Fair,Middletown.More than 70 of the region’s finest crafters and artisans gather at the 325-acre Norman Bird Sanctuary for two days of displaying and offering their creations for sale.For kids, there are pony rides, midway games, and a mud pit; grown-ups can enjoy the bands, food trucks, and beer garden. 10/1–10/2; normanbirdsanctuary.org

Misquamicut Fall Festival,Westerly. Misquamicut State Beach, southwestern Rhode Island’s great stretch of sand on Block Island Sound, turns into a seaside carnival in mid-September with live music, dancing, arts and crafts, food, and midway rides along the shore. Right down the road is Watch Hill, with its shops, restaurants, and antique carousel. 9/16–9/18;misquamicutfestival.org

Smith’s Castle Colonial Harvest Festival,North Kingstown. At Smith’s Castle, a 1678 home built by early Rhode Island settler Richard Smith, the harvest-time festivities have an emphasis on history, with costumed docents leading tours of the “castle.” Enjoy an afternoon of live music, crafters’ displays, games and pumpkin painting for kids, and a scrumptious annual tradition, apple crisp. 9/10;smithscastle.org

VERMONT

19th-Century Apple & Cheese Harvest Festival,Stafford. The Justin Morrill State Historic Site hosts a celebration of two of Vermont’s signature products with tastes of heirloom apples and apple pie, local artisan cheeses, and cider making on an antique press. Learn about life on a small farm like the one that Vermont Senator Justin Morrill lived on here in the 1800s, play period games, and enjoy country fiddling and accordion music. 9/25;morrillhomestead.org

Champlain Valley FAIR,Essex Junction.Vermont celebrates summer’s end with the state’s largest event, welcoming more than 100,000 fairgoers for 10 days of midway games and rides, acrobats and magic, home and garden exhibits, food concessions galore, prize farm animals, and the bounty of Green Mountain agriculture. 8/26–9/4; cvexpo.org

Chester Fall Festival,Chester. Celebrated on the green in a town famed for its stately stone houses, Chester’s foliage-season community party brings artisans demonstrating and selling fine pottery, woodenware, jewelry, fiber art, glass, and more. Kids can meet friendly farm animals, while local foods, concerts, raffles, and field games round out the fun. 9/17–9/18; chesterfallfestival.org

Fall Foliage Festival,Burke. Autumn festivities on East Burke’s village green kick off with a parade, followed by a day of music, horse-drawn wagon rides, craft shows and sales, and even rubber ducky races. There’s a farm animal petting zoo, silent auction, quilt raffle, a live raptor show presented by the Vermont Institute of Natural Science, and an all-day barbecue. 9/24;burkevermont.com

Orleans County Fair,Barton. Along with the rides, food, animal exhibits (4-H even has a dog show), and pulling contests one would expect at a county fair, Orleans County packs its big autumn celebration with special events and attractions: a bike stunt show, mechanical bull riding, marionette performances, a horseback gymkhana, and an appearance by the Axe Women of Maine. This year’s concert stage features an AC/DC tribute band. 9/7–9/11;orleanscountyfair.net

Peru Fair,Peru. Just a short hop from Weston and the Vermont Country Store, and in the shadow of Bromley Mountain, tiny Peru hosts an old-time country fair featuring crafts, antiques, and art exhibits and sales; clowns, magicians, and pony rides for kids; live music and clog dancing; and plenty of homemade foods. Save room, though, for the afternoon’s crowning culinary event, the annual pig roast. 9/24;perufair.org

World’s Fair,Tunbridge. This small-town event with the big name turns Tunbridge into a world apart each September. For 150 years, the fair has stuck to its agricultural roots—you’ll never get closer to 4-Hers’ prize livestock—but has grown to include the rides, food, and entertainment fairgoers love. Visit a one-room schoolhouse, see antique machinery at work, wander a museum filled with artifacts of yesteryear’s domestic life, and take a trackside seat for harness racing. 9/15–9/18;tunbridgeworldsfair.com