5 min read

Winter in Maine means all sorts of outdoor activities, including community festivals and events at some of the state’s ski resorts. It also means annual happenings like Maine Restaurant Week and Maine Maple Sunday Weekend. Here are a dozen ways to hang on and have fun until spring arrives.

Frozen Funk

6-8 p.m. Saturday. Deering Oaks Park, Portland, free. On Facebook.

Deering Oaks Park in Portland is the place to be for a fabulous winter skating party. WMPG’s DJ Shaxx will be spinning quintessential ’80s tunes, and Space will be lighting it all up. The center of the action is the skating rink, but you can also stick to the edges and bust a move in your snow boots. Warm up with a hot chocolate, and spend two hours shaking off the winter chill. Should Mother Nature throw down rain, the party moves to Jan. 24.

Ice carving at the Camden Winterfest. (Photo courtesy of Camden Public Library)

Camden Winterfest

10:30 a.m.-2 p.m. Jan. 31. Camden Public Library Amphitheatre, 55 Main St. librarycamden.org.

This year marks the 23rd anniversary of the Camden Winterfest. Festivities include ice carving, a polar plunge, a dog fashion show, kids’ activities including a story walk, music, food and hot cocoa. The festival is presented by Camden Public Library, and all ages are welcome.

Fire on The Mountain

Snow guns blow snow over skiers as they make their way down Hayburner trail at Sugarloaf. (Gregory Rec/Staff Photographer)

Jan. 30-Feb. 1. Sugarloaf, 5092 Access Road, Carrabassett Valley,$25-$55, 21-plus. sugarloaf.com.

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Fire on the Mountain is the annual gathering of fans of the Grateful Dead and Jerry Garcia who also love to ski and snowboard. The weekend will be packed with a range of live music in the King Pine Room and Widowmaker Bar. Bands include Not Fade Away, Steely Dead, Keller Williams’ Grateful Grass, Marley & Grass, Grateful for Biggie, Shakedown Citi and Rose Alley & Friends.

Biddeford WinterFest

Feb. 6-8. Downtown Biddeford. biddefordmaine.org.

Biddeford loves this time of year, and they’ll prove it to you with their annual WinterFest. Mascot François will be around on Saturday that weekend for high-fives and selfies. This year’s WinterFest schedule includes Piano Men: The Music of Elton John & Billy Joel at City Theater; an adults-only sledding party on Adams Street; food and drinks like pizza and hot cocoa; several performances including Nine Tigers Kung Fu; skating at West Brook skating rink, and more.

Team members Barry Goldberg, Rob Roy, Adam Lachman and Greg Soutiea, who go by the team name Toboggan or Not Toboggan, head down the chute at the Snow Bowl in Camden on Jan. 31, 2025, in advance of competing in the U.S. National Toboggan Championships. (Gregory Rec/Staff Photographer)

35th Annual U.S. National Toboggan Championships

Feb. 6-8. Camden Snow Bowl, 20 Barnestown Road, Camden. toboggannationals.com.

Thrill seekers flock to the Camden Snow Bowl every year for one of the state’s most unique competitions. The star of the U.S. National Toboggan Championships is the huge, 400-foot long wooden chute that delivers sledders onto frozen Hosmer Pond. Teams of two, three or four riders race against the clock to take top honors. Many racers wear costumes, and the weekend draws thousands of enthusiastic spectators.

Pride Weekend

Feb. 6-8. Sunday River. 15 South Ridge Road, Newry. sundayriver.com.

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Pride month in Maine is June, but Sunday River gets a head start every winter with its Pride Weekend. The event is being presented with the nonprofit OutRyders, the largest LGBTQ+ ski and snowboard club in New England. Run by volunteers, OutRyders cultivates friendships and organizes activities on and off the slopes. Be ready to hit Sunday River’s eight peaks during the day, and then partake of après-ski fun.

Maine Snowshoe Festival

10 a.m.-3 p.m. Feb. 14. Roberts Farm Preserve, 58 Roberts Road, Norway. wfltmaine.org/programs-events.

Norway is a snowshoeing hotspot because of its history of snowshoe manufacturing. The annual Maine Snowshoe Festival features snowshoe races, snowshoe yoga, walks and a fashion show. The event also includes music, beer, food and the Norway chili contest. Jumpstart the festivities by hitting the Millie Dunham Contra Dance & Community Supper the night before at the Norway Grange from 4-8 p.m.

Winter Carnival

10 a.m.-1 p.m. Feb. 14. Gilsland Farm, 20 Gilsland Farm Road, Falmouth, $9. maineaudubon.org.

The Winter Carnival at scenic Gilsland Farm is a celebration of winter wildlife and outdoor exploration. The family-friendly event includes the Great Backyard Bird Count, learning about animal tracking, snow science, art, owl-themed activities, hot cocoa and face painting.

Bow Street Market’s offering during the 2025 Fare & Ice tasting event, part of Flavors of Freeport. (Photo courtesy of Visit Freeport Maine)

Flavors of Freeport

Feb. 20 & 21. Downtown Freeport. visitfreeport.com/flavorsoffreeport.

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Flavors of Freeport is an annual celebration of food and fun. Freeport Foodie Lotto runs all month long, and involves collecting stickers from participating businesses for a chance at winning $1,000. On Feb. 20, hit the Fare & Ice grand tasting event at the Freeport Hilton Garden Inn ($25 tickets). Head back to the hotel on Feb. 21 for a dance party with Motor Booty Affair ($40 tickets).

Maine Restaurant Week

March 1-12. Statewide locations. mainerestaurantweek.com.

Happy 17th anniversary to Maine Restaurant Week! The annual event helps to support local restaurants during the off-season. Many offer special menus and pricing during the week. The Crave part of Maine Restaurant week focuses on coffee-inspired dishes, treats and drinks using Coffee By Design coffee at several locations. Flavors of Maine, at Coffee By Design on Diamond Street in Portland on March 9 is a gathering of farmers, foragers, bakers and makers with plenty of samples.

Westbrook Winterfest

March 7. Riverbank Park, Westbrook, free. downtownwestbrook.com.

By the time March rolls around, you’re going to need an infusion of serious fun. Westbrook Winterfest sure fits the bill with bounce houses, s’mores, demonstrations, photo booths, goats, an artisan market, food trucks and more. If that Saturday is rainy, the fest moves to Sunday.

Keith Harris warches a thermomenter while pouring maple syrup out of an evaporator into a bucket in the sugarhouse at Harris Farm in Dayton. (Gregory Rec/Staff Photographer)

Maine Maple Sunday Weekend

March 21-22. Statewide. mainemapleproducers.com.

Few things are more delicious than Maine maple syrup, and there’s an entire weekend dedicated to sampling it, buying it and getting up close and personal with how it’s made. Sugarhouses statewide will be open for public tours and tastings.

Some spots are open on both days, so check the list on the Maine Maple Producers website at mainemapleproducers.com. Pancakes, anyone?

Editor’s Note: This story was updated on Jan. 17 to correct the locations of Sugarloaf and Roberts Farm Road.

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Aimsel Ponti is a music writer and content producer for the Portland Press Herald. She has been obsessed with – and inspired by – music since she listened to Monkees records borrowed from the town...

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