By Brian Kevin & Bhavana Scalia-Bruce
Updated August 2025
In Maine, the end of summer always stings a little. Farewell, beach days. Goodbye, ice cream for dinner. But it’s not all bad. The silver lining is that fair season kicks off just as the temps start to dip. Suddenly, weekends are filled with fried dough, tractor pulls, blue-ribbon pies, and all the small-town chaos that makes this stretch of the year so fun. It’s bittersweet, sure, but trading sandy sunsets for Ferris wheels and fairground lights isn’t too shabby, after all. Here are 12 fairs and fests to put on your radar.
Common Ground Country Fair | Unity | September 19–21, 2025
Three days of food, music, and all things Maine, the Common Ground Country Fair gathers close to 70,000 people with a mix you won’t find at your average midway. Think: organic farm stands, sheepdog demos, draft-horse shows, local crafts, contra dancing, and farm-fresh eats that actually taste good. Add in hands-on workshops, a zero-waste mission that works, and enough fiddles and folk music to soundtrack the weekend. $25, kids 12 and under free.
Down East Staff Pick: “The Common Ground Fair is the greatest of all time!” — Tara Rice, photo editor
Cumberland County Fair | Cumberland | September 21–27, 2025
More than a week of events and entertainment in Maine’s most populous county, this agricultural fair attracts upwards of 50,000 people for all the usual attractions — fair food, midway rides, animal barns, harness racing, pie contests, oxen pulls — plus a few next-level spectacles, including a rodeo, a motocross show, and an eye-popping fireworks display. $15, kids 12 and under free.
Down East Staff Pick: “Growing up, my elementary school would always throw seasonal celebrations, complete with game booths, hayrides, and cake walks. As a not-much-more mature adult now living in the real world, I still seek out a fair or festival to attend each autumn. This year, the Cumberland Fair’s on my radar. A demolition derby, rodeos, local musicians rockin’ out … I mean, c’mon!” — Charlie Pike, editorial assistant
Maine Needham Festival | Wiscasset | September 27, 2025
The Maine Needham Festival takes over the Maine Tasting Center for its third year. A needham is one of the most Maine-coded confections there is — a sweet coconut-and-potato filling dipped in chocolate. This fest is dedicated to celebrating that quirky classic, with needham-making demos, candy vendors from all over the state, and plenty of opportunities to taste and stock up on the good stuff. But it’s not just about candy. Live music, kids’ activities, crafts, contests, games, and food vendors keep the day feeling more like a full-on block party than just a sweets stop. Free.
Freeport Fall Festival | Freeport | October 3–5, 2025
Nearly 200 Maine artists and makers take to the streets of Freeport, pitching tents at four locations around town, including the Freeport Village Station courtyard and outside the L.L.Bean flagship store. Wall art, jewelry, clothing, books, consumables — there’s very little a sidewalk shopper can’t find. Handmade fishing lures? You bet. Soap made of goat’s milk? Check. Scrimshaw? Absolutely. Live music skews towards bluegrass and Americana, and local businesses and nonprofits sponsor kids’ activities that include nature crafts with the eco-focused Wolfe’s Neck Center and printmaking with Freeport Community Services. Free.
Fryeburg Fair | Fryeburg | September 27–October 5, 2025
The granddaddy of Maine’s agricultural fairs got its start in 1851, when a handful of western Maine towns (and later, some New Hampshire ones) founded the West Oxford Agricultural Society and started throwing an annual harvest-season jubilee. The current fairgrounds date to 1885, and fruits of the farm still take center stage in the pavilions and the livestock barns and arenas. Of course, you don’t need to be a farmer to be on your feet and cheering during the pig scramble, when cute kids chase a passel of cute piglets, or the famous skillet and anvil throws, when brawny women and men, respectively, take turns lobbing a hefty chunk of steel, competing for distance (and, unofficially, for style). On the fair’s first Monday, woodsman teams from around the country gather to compete in everything from ax throwing to pole climbing to crosscut sawing. Of course, there’s a midway, a grandstand stage full of rock and country acts, a variety of truck and tractor pulls, and all the jumbo doughnuts and whoopie pies and deep-fried Oreos your arteries can handle. $17, kids under 12 free.
Acadia’s Annual Oktoberfest and Wine Tasting | Bass Harbor | October 10–11, 2025
Two days, one tiny harbor town, and a whole lot of beer. Acadia’s Oktoberfest, in Bass Harbor, kicks off with the annual Friday night wine tasting, then Saturday turns into a full-blown brewfest with local pours, live music, and a craft tent for when you need a break from drinking. Expect stein-holding contests, keg tosses, giant beer pong, and even belt-sander races (yes, really). It’s basically a block party on the edge of Acadia — with a buzz. $35.
Damariscotta Pumpkinfest and Regatta | Damariscotta | October 10–13, 2025
Some towns carve pumpkins; this one races them down a river. Damariscotta’s Pumpkinfest & Regatta is four days of pure gourd chaos — giant pumpkins lining the streets like oversized art projects, record-breaking weigh-offs, parades, pumpkin derby races, pie-eating contests, a pumpkin drop that’s basically demolition derby meets Halloween, and this year a new 5K dubbed the Tour de Gourd. The main event? Locals hollow out thousand-pound pumpkins, climb inside, and paddle or motor them across the river. It’s festive, it’s absurd, and it’s exactly what makes fall in Maine worth looking forward to.
Down East Staff Pick: “The Damariscotta Pumpkinfest and Regatta is a lot of fun. They have these giant pumpkins that they carve and decorate. And then they’ll take giant pumpkins and turn them into boats to race on the Damariscotta River, which I look forward to every year!” — Jackson Long, digital coordinator
Sunday River Fall Fest | Newry | October 11–12, 2025
It’s prime time for a foliage road trip through the western Maine mountains, and this between-the-seasons fest is a great pit stop if you want to wet your whistle, take a scenic chondola ride, or wrap your arms and legs around your spouse and dive into a mud pit. Wait, what? The centerpiece of the fest is the spectator-friendly North American Wife Carrying Championship, a more than 20-year tradition at Sunday River, based on a Finnish practice of husbands carrying wives over their shoulders while racing through an obstacle course — Sunday River’s includes logs to surmount and a mud pit, and attracts dozens of couples from all over the country. The winning pair wins cash and the wife’s weight in beer (measured using a large seesaw). More subdued highlights include live music, a beer garden, a cornhole competition, and an annual gear sale at the resort’s ski shop. Free.
Swine & Stein Brewfest | Gardiner | October 11, 2025
It’s not the world’s most authentic Oktoberfest celebration, but that doesn’t make this loosely Bavarian-themed street fest on the Kennebec River any less fun. Breweries (and wineries and distilleries) serve samples along Gardiner’s Water Street, while food vendors sell pork products and bands take to two stages. The real action, though, is in the goofy street games and contests, with revelers going head-to-head in bouts of human-scale Jenga, a Rochambeau championship, a juried beard-and-mustache pageant, and more. The most fun to watch is the frozen–T-shirt competition, in which blindfolded contestants, some tipsier than others, try to be the first to unfold and put on an icebound tee. Munich it isn’t, but you can likely still find a drinking buddy wearing lederhosen or a dirndl (that’s a Bavarian beer-maid’s dress). $45 ($10 without a wristband for alcohol).
Harvestfest | York Beach | October 18, 2025
A juried craft fair with upwards of 100 makers and artisans is at the heart of Harvestfest, on and around Short Sands Beach. Plus, live bands, food trucks, and a kids’ fest that includes face painting and train rides. This year’s fest will include live music from Freight Train and Dan Blakeslee (aka Dr. Gasp), who will be playing under the tent on the ballfield. Kidsfest is also back, with plenty to keep everyone busy: the Roaming Railroad will be running inside York’s Wild Kingdom, and there will be free games such as ring toss, bean-bag buckets, and giant Connect Four. The Portsmouth Naval Shipyard STEM Outreach team is bringing a hands-on bristlebot station, where you can build your own mini robot that zips around and can be re-engineered as many times as you like. Free.
Down East Staff Pick: “My mother-in-law and I usually have a booth for Baloo Baleerie in the DE shop. We have to skip this year, but we’ve been part of it for at least seven years. The vendors are always great, and I’ve heard the rest of the festival is wonderful too, though I hardly ever get to see it since my booth keeps me so busy.” — Sally Cameron, sales project manager
Harvest on the Harbor | Portland | October 30–November 1, 2025
A celebration of food and drink and the culinary whizzes behind them, this series of individually ticketed events — seated dinners, tasting parties, chef competitions — takes place in various locations across New England’s foodiest town. This year’s highlights include a blind wine tasting and how-to classes with Maine distillers and mixologists, plus an oyster festival, where aquaculturists from up and down the coast offer oysters and insight into their growing process — maybe even a quick shucking lesson. Free.
