By Brian Kevin
From our October 2021 issue
Cumberland County Fair | Cumberland
September 26–October 2
More than a week of events and entertainment in Maine’s most populous county, Cumberland’s 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 suitable to the festival’s scale, including a rodeo, a motocross show, and an eye-popping fireworks display. $12, kids 12 and under free.
Freeport Fall Festival | Freeport
October 1–3
Nearly 200 Maine artists and makers take to the streets of Freeport, pitching tents at four locations around town, including at 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. New this year is a mini oyster festival, with a half-dozen Casco Bay growers stationed at Freeport’s town hall, sharing tidbits about how oyster farms help keep Maine waters healthy while visitors slurp their wares. 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, printmaking with Freeport Community Services, and writing and drawing comic books with DotCom Comics & Collectibles. Free.
Fryeburg Fair | Fryeburg
October 3–10
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 exhaust-belching truck and tractor pulls, and all the jumbo donuts and whoopie pies and deep-fried Oreos your arteries can handle. $13, kids under 12 free.
Swine & Stein Brewfest | Gardiner
October 9
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).
Sunday River Fall Festival | Newry
October 9–10
It’s prime time for a foliage road trip through the western Maine mountains, and this between-the-seasons fest at Sunday River ski resort 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 mudpit. 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.
Harvestfest | York Beach
October 16
A juried craft fair with upwards of 100 makers and artisans is at the heart of York’s fall fest on and around Short Sands Beach. Plus, live bands, food trucks, and a kids’ fest that includes face painting and train rides. Free.
Harvest on the Harbor | Portland
November 4–7
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 all across the state offer oysters and insight into their growing process — maybe even a quick shucking lesson.
As the COVID pandemic continues into the fall, cancellations and gathering restrictions remain possibilities. Check websites for updates about festivals and events, and use common-sense precautions on your Maine fall travels. If you are not yet vaccinated, please visit maine.gov/covid19/vaccines to find a vaccination site in your neighborhood. The print version of this story included entries for Common Ground Country Fair and the Whoopie Pie Festival, which have been canceled, and the Damariscotta Pumkinfest, which has been curtailed.
