Whether you’re looking to bundle up and hit the ice, soak in some culture, or just find a cozy corner with a glass of red, Portland, Maine delivers. Here’s your go-to guide for winter activities, sorted by mood and type of experience.

For the Festive at Heart

These events bring out the holiday magic, think twinkle lights, carolers, and classic Christmas nostalgia.

  • Christmas Tours at Victoria Mansion | Nov 28–Jan 4
    Step into a Gilded Age wonderland, where each room is decorated by local designers with period-appropriate flair. History buffs and holiday romantics, this one’s for you.
  • Christmas Prelude in Kennebunkport | Dec 4–14
    Just 40 minutes down the coast, Kennebunkport transforms into a Hallmark movie. Tree lightings, lobster trap decor, and seaside charm galore.
  • Maine Narrow Gauge Polar Express Ride | Nov–Dec
    All aboard for hot cocoa, cookies, and a dramatic reading of The Polar Express. This family-friendly train ride to the “North Pole” is pure childhood joy.
  • Holiday Decor at Batson River Brewing
    This brewery and yummy spot goes all out with its over-the-top holiday decorations. Grab a spiked cider and soak it in.

For the Culture Seekers

Craving music, art, or a touch of ballet? These activities are for the aesthetes and romantics.

  • Portland Symphony Orchestra: Magic of Christmas | Dec 12
    A beloved tradition. Expect holiday classics, choir harmonies, and a few goosebumps.
  • A Victorian Nutcracker by Portland Ballet | Dec 16
    A dreamy, period-inspired take on the classic tale, elegant, nostalgic, and oh-so-Portland.
  • Portland Museum of Art Free Fridays | Every Friday, 4–8 PM
    Art that’s both inspiring and free? Yes, please. Wander the galleries, warm up indoors, and discover something unexpected.

For the Outdoorsy Types

You don’t have to wait for summer to enjoy Maine’s natural beauty. Winter brings its own kind of fun and fresh air.

  • Outdoor Ice Skating at Thompson’s Point | Dec–March
    Lace up and glide riverside. Bonus: food trucks and cocoa make this a solid date night or family outing.
  • Cross-Country Skiing in the City
    When the snow piles up, head to Riverside Golf Course or Deering Oaks Park. Both spots offer serene trails and that quiet-crunchy snow sound we all secretly love.
  • Cheer on the Maine Mariners
    Winter sports and a social outing? We’re in. Catch a game at Cross Insurance Arena and join the roar of the crowd.

Credit: Astraea Wellness Spa

For the Ones Who Just Want to Get Cozy

If your perfect winter day includes slippers, steam, and good food, we see you. And dont’ worry, Portland knows how to do cozy.

  • Astraea Spa Infrared Sauna Suites
    These private infrared sauna suites offer a luxurious escape in the restorative ritual of hot, cold, and rest – complete with a persona rain shower and cozy relaxation area.
  • Wayside Tavern
    This is one of our favorite local spots, and some of the best bites in town. Slide into Wayside for an intimate, inspired meal. Comfort food, refined, right next door to the Francis.

Winter might just be the best-kept secret in Portland. Things slow down a little, but there’s still so much to see, do, and enjoy, without the summer crowds. Whether you’re here for the food, the culture, or just a cozy getaway, Portland in the winter is welcoming, relaxed, and full of local charm. We’d love to have you.

Image credit: Tim Greenway

Abigayle Clark

Abigayle Clark is the General Manager of The Francis, where historic character meets modern hospitality in the heart of Portland. She’s a go-to for local insight, and when she’s not at the hotel, she’s likely hanging with her cat George or skating with her roller derby team.
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