Paint the Town Red-Kennebunkport
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16 Cheery Winter Events in Maine to Cure the Blues

Perhaps no other state in the country celebrates winter as much as Maine. Across the state, annual traditions celebrate everything from skiing to maple syrup. If you have ever wanted to know how people in Maine handle the winters, this is where you’ll find out.

Most winter events in Maine are held at least 50% outdoors, so you should plan for proper layering of clothes and accessories. However, we’re thrilled to see options like heated seats and climate-controlled tents to shake off the shivers.

Here are the top Maine festivals to enjoy this winter. And, remember that a Maine winter is also a great time to get discounts at many luxury hotels.

Paint the Town Red-Kennebunkport
Paint the Town Red | photo via cindyfitzmorris

Paint the Town Red

Kennebunk/Kennebunkport/Arundel

Love is in the air during February across the Kennebunks (Kennebunk and Kennebunkport), living up to the nickname “New England’s Most Romantic Town.”

Instead of just one event, “Paint the Town Red” runs all month with each hotel, business, and restaurant designing discounts and special packages for couples.

Fill a chapter of your own love story in this romantic winter setting. You can still walk on the beaches, explore Dock Square, and enjoy the impressive dining scene.

Vertical Challenge

Saddleback Mountain

The Rangeley Lakes Resort is back again after closing down for five years starting in 2015, and one of the newest events from the creative team is the Vertical Challenge. While that name sounds intimidating, it’s an all-ages, all-abilities, all-skill levels event focused on amateurs.

Even if you don’t want to hit the slopes, hop around the carnival at the base of the mountain with fun games and booths with samples and swag.

Snow Bowl

Caribou

The most epic snowmobile show happens in Caribou for five days in February or March. The Snow Bowl lets riders show off their skills, race for a jackpot, and even cross the international border into Canada.

You don’t even have to know a snowmobile from an ATV to enjoy this because the festival includes food tours, after-dark parties, and monster trucks. Best of all? There’s no admission charge!

TIP: Bring your passport if you plan on crossing into Canada, even on a snowmobile.

Flavors of Freeport

Freeport

Freeport knows how to throw a party in any season, but winter is time for the Flavors of Freeport festival. Eat your way through samples from the best restaurants in town, including the one owned by L.L. Bean’s granddaughter.

Wander around the food fiesta during the Frosty Frolic, and burn some of those calories at the Freeport Dance Party. It’s all headquartered around the L.L. Bean Flagship Store and outlet mall across the way.

Snowshoe Festival

Norway

The Bean Boot isn’t the only footwear that helped make Maine famous. Norway was once the “Snowshoe Capital of the World,” with major brands headquartered here starting in the mid-1800s.

Even though new technology and transportation took over in the mid-20th Century, Norway still proudly boasts its shoemaking history with the annual Snowshoe Festival. Races, recreational games, and contra dancing make this event fun for all ages. One event is even touted as “Just like the Olympics, only more awkward.”

Sled Dogs-Fort Kent
Sled Dogs | photo via aparadis.photography

Can-Am Crown International Sled Dog Races

Fort Kent

The Can-Am Crown International Sled Dog Races are a doggone good time, spanning 250 miles while originating in Fort Kent. You can also find a viewing spot in Allagash or Portage.

This is a serious event because the winner qualifies for the famous Iditarod. Spectators can enjoy an old-fashioned snowmobile parade as well.

TIP: Bring your passport for this one because Fort Kent is right at the Canadian border.

Belfast Ice Festival

Belfast

The community of Belfast carves out one weekend each winter for the Ice Festival. Activities range from ice rowing on the harbor to enjoying local brews at one of several downtown Belfast breweries.

Meander through the various ice carvings, and take a class to learn your own ice design skills. Sledding, sleigh rides, and luminary night walks are also offered among the robust list of things to do during the Ice Festival.

Electric Mountain & Fire on the Mountain

Sugarloaf Mountain/Carrabassett Valley

It’s hard to pick just one of the fun winter events at Sugarloaf, so we’ll highlight two of them:

  • You’ll be a tried and true “Loafer” after experiencing the early January magic of EDM music, a sea of neon, and all the epic skiing options at this Maine ski staple.
  • Early February is for deadheads, with the 5th Annual Fire on the Mountain celebration of the Grateful Dead.

TIP: Tickets for these events will sell out quickly. Book as soon as you can after they go on sale.

Winter Festival

Pleasant Mountain/Bridgton

Pleasant Mountain is a ski resort on the west side of Moose Pond. Every year after Christmas, it hosts a Winterfest celebration in late December. Guests participate in a torchlight parade, walking out to see the best views of the fireworks. Before and after, you can enjoy live music, food, and drinks at Blizzard’s Pub.

Somerset Snowfest

Somerset

If there’s one event summer lovers should just suck up the winter temperatures for, it’s Somerset Snowfest. Of course, the obvious celebration of transitional winter sports is there. However, it’s the skijoring that really makes this one stand out.

DEFINITION: Skijoring is a winter sport where a person rides a horse while another person riding skis is attached to the horse. Think of it like waterskiing with a horse instead of a boat and snow instead of water.

Other competitions include kite flying, downhill kayak racing (on snow), and the famous ice bar.

Ice Fest-Belfast
Belfast Ice Fest | photo via sjoy1979

The Big Rockland Chill

Rockland

The Stand Theatre has been a Rockland performance venue for 100 years now, but it’s also home to one of the newest winter festivals in Maine. 2024 marks the second year for The Big Rockland Chill in Oak Street Alley behind the theatre, with special showings and events inside.

It’s a family-friendly event that even your pet will love because there’s a parade for four-legged friends. Also intriguing is the Yeti Dance Party.

Long Lake Ice Fishing Derby

St. Agatha

Late January brings ice anglers from all over the world to compete in this small, remote town in Aroostook County. The competition runs for two days across 10 waterways. Categories for adults and kids mean there’s potential prize money for everyone.

If you’re an angler hesitant about the cold, maybe the 8-pound salmon or 18-pound lake trout will warm up your motivation.

Winterfest

Bucksport

The winter buck stops in Bucksport for one day in late January to celebrate all things winter. It’s held at the Bucksport Golf Club and includes snow sculpture competitions, sledding, and ice skating. Plenty of hot chocolate and warm treats will be available.

Before or after, head across the Penobscot River to Winterport. The Winterport Winery might have the perfect wine or cider to warm you up.

U.S. National Toboggan Championships-gsoutiea
U.S. National Toboggan Championships | photo via gsoutiea

U.S. National Toboggan Championships

Camden

The U.S. National Toboggan Championships is one of the most popular winter events in Maine. While the name sounds formal, you’ll be amazed at this wood toboggan race’s laid-back yet competitive vibes in Camden.

You can even put your name in the running because beginners are welcome. Crazy costumes, unique team names, and cold beer in the dead of winter are all hallmarks of this tradition.

Here’s how it works — Two to four-person teams ride a 400-foot-long wooden toboggan chute that rises 70 feet in elevation. Toboggans can reach speeds of up to 45 mph. Also, this dog-friendly event brings out spectators galore.

Ice Harvest Day

South Bristol

We might take for granted how easy it is to get ice these days, but Ice Harvest Day at The Thompson Ice House Harvesting Museum takes you back to the pre-refrigeration days. Maine was once an industry leader in ice harvesting, transporting millions of tons down the Kennebec River to be shipped worldwide.

This one-day event takes you from the museum full of ice harvest tools to frozen Tompson Pond to harvest some ice with others. You’ll have a whole new appreciation for your ice dispenser.

Maple Syrup Sunday

Statewide

Maine is the largest producer of maple syrup in the United States, and maple sugaring is an important part of the state’s history and culture. While it’s a bit outside of winter (it will still feel like winter), Maine Maple Sunday is an annual event held on the fourth Sunday in March to celebrate the start of maple sugaring season in Maine.

Sugarhouses across the state open their doors to the public, offering tours, demonstrations, and freshly made maple syrup samples. You’ll get to help tap a tree and participate in other festivities unique to each farm.

Maine Maple Sunday
Maine Maple Sunday | photo via thehomesteadyrambler

A Few Last Tips for Winter Events in Maine

Maine schools generally get a week off in February. Planning a trip around this week might bring more winter activities but larger crowds — especially to ski resorts.

As you get closer to planning your trip, see if the dates have been set for Portland’s Carnaval or Biddeford’s WinterFest. Plus, you’ll find a festive winter spirit everywhere in Maine as locals embrace the season.

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