Maine’s Winter Playlist

Ten Unique Experiences You Can’t Find Anywhere Else This Winter

The cooler weather never slows us down; in fact it fuels the region’s creativity, sparks our adventurous spirit, and transforms Greater Portland into a bustling winter playground. With equal opportunities for exploration, relaxation, and fun, Portland and its charming surrounding towns and islands make the perfect winter escape.

From sipping craft cocktails at cozy hotel rooftop bars or heated igloos to exploring iconic lighthouses dusted in snow, every corner of this city has something special to offer. Dive into 10 winter experiences you can’t miss this season, whether it’s indulging in a relaxing spa retreat, marveling at our vibrant arts scene, or tasting your way through seasonal menus at award-winning restaurants.

Winter in Portland is an invitation to experience the season in ways you won’t find anywhere else.

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1. A Bounty of Maine Winter Flavors

Portland is no stranger to culinary accolades, earning recognition from Bon Appetit to Travel + Leisure for its foray into foodie excellence. In 2024, CNN named Portland one of “America’s Best Towns to Visit.” Winter flavors in Portland elevate these foodie experiences to a whole new level. Seasonal menus highlight the best of Maine’s winter harvest like hearty root vegetables and seafood caught fresh from the bay. The talented local chefs take these winter ingredients to new heights, creating innovative dishes that celebrate both tradition and creativity.

WInter is the perfect time to try a sampler of freshly-shucked oysters, maybe even learn to shuck a few yourself. It’s a seafood delicacy that tastes sweeter when its in season over the cooler months. Visit local bakeries for indulgent maple-glazed pastries and hot cider, or treat yourself to the winter-exclusive prix fixed menus at fine-dining establishments. With fewer crowds and shorter wait times, winter is the perfect season to explore Portland’s food scene at your own pace.

Get inspired by Portland’s culinary scene on the Restaurants page.

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2. The Magic of a Winter Working Waterfront

Portland’s working waterfront doesn’t take the season off. In fact, winter just offers a quieter, more intimate way to experience its New England charm. Fishing boats continue to haul in fresh crustaceans, while the Casco Bay Lines ferries operate year-round, offering unparalleled views of Maine’s snow-dusted coastline. The Mailboat Run is a winter highlight, combining the efficiency of a working ferry route with the beauty of a scenic cruise.

For a magical evening, watch the Old Port light up with the Pandora Winter Lights put on by Portland Downtown. These dazzling light displays transform the trees, cobblestone streets, and working waterfront into a sparkling wonderland, creating an atmosphere that feels both festive and whimsical. Explore the quaint downtown pathways uncovering local shops, lounges, bars, and murals and public art around every corner.

Get inspired by Portland’s waterfront charm on the Things to Do page.

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3. Have a Transformative Experience at a Wellness Spa

Winter in Portland isn’t just about braving the cold; it’s also about finding warmth and relaxation. Portland’s spa scene has blossomed into a haven for wellness enthusiasts, offering luxurious treatments that soothe both body and mind. Adeline Wellness Spa at The Westin has undergone a stunning transformation, introducing treatments inspired by Maine’s natural beauty. Similarly, the newly opened Longfellow Spa provides a boutique experience that feels both indulgent and deeply personal.

Whether you opt for a seaweed wrap, a hot stone massage, or a hydrating facial, these spas deliver more than just relaxation—they offer a moment of escape. Many spas also feature Maine-made products, allowing you to take home a piece of the experience. Don’t miss the chance to recharge in one of Portland’s serene wellness spaces.

Get inspired by Portland’s wellness offerings on the Spas and Wellness page.

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4. Immersive Yourself in Public Art and Local Talent

Portland is an artistic powerhouse, and winter showcases the city’s creative energy in unique ways. Thanks to Creative Portland’s Art App, visitors can take a self-guided tour of public art installations, from murals to sculptures, all while exploring the city’s charming streets. Each piece tells a story, making your walk through Portland feel like a curated exhibit.

For an even deeper dive, don’t miss the First Friday Art Walk. Held monthly, this beloved event transforms Portland into a hub of artistic expression, with galleries, pop-up exhibits, and live performances creating an electrifying atmosphere. Winter is the perfect time to immerse yourself in the city’s creative soul. Everything around the city from its utility boxes to its bus shelters are curated with art as a tribute to our local artists and a space for the community’s spirit and creativity to flow through and visitors to marvel at.

Uncover Portland’s local art scene and headlining touring acts on the Arts and Culture page.

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5. Sip Portland’s Craft Beverages

Portland is a craft beverage mecca, offering much more than just beer. While its breweries are world-renowned—think Allagash and Geary—the city also excels in creating seasonal wines, ciders, and spirits. Winter in Portland is the perfect time to indulge in these flavors, whether you’re enjoying a flight of winter ales or sipping a hot toddy at a cozy distillery.

Many of these establishments host events like tastings, trivia nights, and even brew-your-own experiences, making them a fun and interactive part of your Maine winter escape. And don’t forget to try Shipyard’s seasonal sodas, like Eli’s blueberry or black cherry, for a non-alcoholic taste of Maine.

Get inspired by Portland’s beverage offerings on the Breweries and Distilleries page.

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6. Cozy Up at Unique Accommodations

Portland’s hotels and inns are designed for winter comfort, offering everything from roaring fireplaces to light-up outdoor igloos. The Portland Harbor Hotel’s seasonal dining spaces provide a whimsical experience, while boutique accommodations in the Old Port offer a blend of history and modern luxury.

Many hotels feature on-site amenities like spas, lounges, and restaurants, making them perfect for a snowy day spent indoors. Winter rates are often more affordable, giving you the chance to indulge in Portland’s renowned hospitality without breaking the bank.

Get inspired by Portland’s accommodations on the Where to Stay page.

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7. Celebrate Local Events and Festivals

Portland’s winter calendar is brimming with must-do New England experiences. Maine Restaurant Week in March offers the perfect excuse to explore the city’s dining scene, with special menus and deals at participating restaurants. Meanwhile, Thompson’s Point becomes a hub of winter activity, featuring ice skating, live music, and cozy lounge spaces.

For art enthusiasts, the Portland Museum of Art’s seasonal exhibits provide a cultural escape, like Art in Bloom annually in February. While local breweries host year-round trivia nights, book clubs, and other community events. Winter in Portland is a celebration of creativity where you can come together with our community around hobbies you have passion for from sports to crafts to music.

Get inspired by Portland’s events on the Events Calendar.

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8. Embrace Sustainability

Portland is a pioneer in sustainable and regenerative tourism. Businesses like Allagash Brewing and Inn by the Sea lead the way with eco-friendly practices that prioritize the environment. From recycling brewing byproducts to sourcing local ingredients, these efforts make Portland a destination you can feel good about visiting.

Explore shops, restaurants, and attractions that embrace environmental efforts, and know that your visit contributes to a community dedicated to preserving Maine’s natural beauty for generations to come.

Get inspired by some of Portland’s green initiatives on the Sustainability page.

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9. Shop Maine-Made

Portland’s boutiques and markets are treasure troves of Maine-made goods, from handcrafted jewelry to artisanal homewares. Explore Portland’s downtown and Art’s district for unique finds, or head to Freeport (just 30 minutes north) and the Maine Mall in South Portland for a wider selection of shops and outlets. Winter deals and pop-up markets offer even more opportunities to discover local souvenirs and post-holiday sales.

Whether you’re looking for a keepsake or the perfect gift, Portland’s shops capture the spirit of Maine in every item.

Get inspired by Portland’s boutique and unique shop options on the Shopping page.

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10. Hit the Slopes and Trails

Winter sports are a cornerstone of the Maine experience, and Portland is perfectly positioned to access it all. Just two hours from ski lodges and resorts like Sunday River and Sugarloaf, you can spend the day skiing or snowboarding before returning to the city for an evening of fine dining and entertainment.

Prefer a closer adventure? The Scarborough Marsh and Back Cove offer scenic snowshoeing and winter hikes, blending the beauty of nature with the convenience of a city escape. Portland truly offers the best of both worlds.

Get inspired by Portland’s outdoor activities on the Outdoor Activities page.

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Plan Your Winter Escape

Portland, Maine, transforms into a haven of coastal charm and adventure in winter. From iconic culinary experiences to outdoor adventures and artistic exploration, there’s no better place for your New England winter getaway.

Make this the season you embrace the magic of a New England winter. Every moment feels can’t miss experience in Maine.

Start planning your trip today by using our Trip Planner or viewing more articles and itineraries on our blog.