While Peaks Island in Maine is an iconic summer destination, it holds an undeniable charm during the winter months. The island's serene landscapes and quieter streets create the perfect setting for those seeking a peaceful retreat. But when the allure of cozy island life meets the call for a little winter adventure, a day trip to Portland, Maine, offers the best of both worlds.
Just a short ferry ride away, Portland transforms into a winter wonderland filled with warm indoor attractions, vibrant local businesses, and plenty of opportunities to embrace the season. From world-class art galleries to charming coffee shops and boutique shopping districts, the city is brimming with activities to fill a day (or two!) of exploration.
If you're staying on Peaks during the colder months, read on to discover how a quick trip into Portland can add a spark of adventure to your winter stay.
1. Warm Your Soul at Portland’s Coffee Shops
When the cold winter air greets you, there’s no better way to start your day in Portland than by stepping into one of its many welcoming coffee shops. Portland is renowned for its exceptional coffee culture, where independent roasters and cafés take pride in delivering high-quality brews with a cozy ambiance.
Start your morning at Tandem Coffee Roasters, where the aroma of freshly roasted coffee beans greets you the moment you walk in. Tandem is known for its expertly crafted pour-overs, espressos, and delicious baked goods. Don’t miss their iconic biscuits served warm with seasonal jam—comfort food at its finest.
Speckled Ax For coffee lovers seeking something unique, Speckled Ax is a must-visit. This café specializes in wood-roasted coffee, a method that imparts subtle smokiness to their beans. Pair a latte with one of their house-made pastries for a delightful start to your Portland adventure.
A Portland staple, Coffee By Design offers several locations throughout the city, making it a convenient stop no matter where you wander. Their locally roasted beans make a great souvenir to take back to Peaks Island!
2. Immerse Yourself in Art and Culture
Portland’s thriving arts scene is a year-round attraction, but winter offers a special opportunity to experience its cultural gems without the summer crowds. Whether you’re an art enthusiast or just curious, the city’s galleries and museums promise hours of inspiration.
The Portland Museum of Art is an absolute must-visit. Located in the heart of downtown, the museum features an impressive collection of American and European art, as well as pieces from Maine’s vibrant local artists. In winter, the PMA often hosts seasonal exhibitions, providing fresh reasons to return time and again.
If contemporary and experimental art is more your style, head over to SPACE Gallery. This nonprofit venue showcases cutting-edge works by emerging artists, along with film screenings, live performances, and community events.
Congress Street’s Independent Galleries Stroll along Congress Street, where you’ll find an array of smaller galleries like Greenhut Galleries - and Portland Art Gallery. These spaces highlight the creativity of Maine-based artists, offering everything from landscape paintings to modern sculptures.
3. Shop Local in Portland’s Boutique Districts
Winter in Portland is also the perfect time to explore the city’s diverse shopping districts. From charming boutiques to specialty stores, Portland is a haven for finding unique treasures while supporting local businesses.
Old Port District
The Old Port is Portland’s historic waterfront district, and its cobblestone streets lead to some of the most picturesque shops in town. Here, you’ll find everything from handcrafted jewelry to Maine-inspired home décor. Be sure to stop by Treehouse Toys if you’re traveling with kids or looking for whimsical gifts.
Vintage lovers won’t want to miss the Portland Flea-for-All. This eclectic marketplace is packed with antiques, retro finds, and artisanal goods. It’s the perfect spot for discovering one-of-a-kind souvenirs or adding to your personal collection.
Local Craft Stores
For those who appreciate handmade goods, visit stores like Maine Craft Portland and Folly 101 where you’ll find beautifully crafted pottery, textiles, and more. These items make wonderful gifts or keepsakes to remember your trip.
4. Savor Portland’s Culinary Delights
After a morning of coffee, art, and shopping, warm up with a delicious meal in one of Portland’s renowned restaurants. The city is a foodie’s paradise, even in winter, with hearty dishes that’ll leave you feeling satisfied and cozy.
You can’t visit Portland without indulging in some fresh seafood, and Eventide Oyster Co. delivers an unforgettable experience. Their famous brown butter lobster roll is a wintertime treat that pairs perfectly with a hot bowl of clam chowder.
Duckfat is another winter favorite, known for its indulgent Belgian-style fries cooked in—you guessed it—duck fat. Pair them with a warm panini and one of their house-made sodas for a meal that’s as comforting as it is delicious.
This beloved neighborhood eatery serves up Southern-inspired comfort food with a Maine twist. From savory shrimp and grits to their legendary biscuits and gravy, Hot Suppa is the ultimate winter dining destination.
5. Cozy Up with a Book or a Pint
Portland’s charm extends to its intimate bookstores and craft breweries, making them perfect stops for unwinding on a winter afternoon.
Sherman’s Maine Coast Book Shop
Escape the cold and browse the shelves at Sherman’s, Maine’s oldest bookstore. Located in the Old Port, this cozy shop offers everything from bestsellers to local authors. Grab a book and take a piece of Maine’s literary culture back to Peaks Island.
Portland’s Breweries
Warm up with a tasting at one of Portland’s many craft breweries. Popular spots like Allagash Brewing Company and Bissell Brothers serve up seasonal brews that are perfect for winter. Whether you’re a beer connoisseur or just looking to try something new, the city’s brewery scene is not to be missed.
6. Explore Indoor Adventure Activities
For a touch of excitement, Portland also offers indoor activities that are perfect for the whole family or adventurous couples.
Test your wits and teamwork at one of the city’s escape rooms. These interactive experiences are not only fun but also a great way to stay warm and engaged during a winter afternoon.
While primarily known for its summer events, Thompson’s Point has plenty to offer in winter. Check out its indoor skating rink or grab a drink at Bissell Brothers while enjoying live entertainment.
7. Take in the Waterfront Views
Even in winter, Portland’s waterfront offers an unforgettable experience. The calm, icy waters of the harbor glisten under the soft glow of city lights, creating a tranquil atmosphere that feels almost magical. Bundle up in your coziest layers and take a leisurely stroll along the Eastern Promenade, where you’ll be rewarded with panoramic views of Casco Bay and its surrounding islands. You might even spot a few hardy boats bobbing in the harbor, their lights reflecting beautifully on the water.
If you prefer to stay closer to the ferry terminal, the views there are equally captivating. Watching the ferries glide across the water as the sun sets or the moon rises is a serene way to end your day. The crisp winter air has a way of sharpening the colors and sounds of the waterfront, making the experience all the more vivid. Whether it’s the stillness of the harbor or the distant hum of activity on the docks, the beauty of Portland’s waterfront in winter is a sight you won’t soon forget. Afterward, head back to Peaks Island and let the calming rhythm of the waves set the tone for a peaceful evening.
Plan Your Winter Adventure Today
If you’re staying with us on beautiful Peaks Island, you already know the charm of a peaceful retreat surrounded by stunning ocean views. But just a quick ferry ride away, Portland awaits with its cozy winter charm and vibrant attractions. A day trip to the city offers the perfect mix of adventure and relaxation, even during the colder months.
Warm up with a visit to Portland’s inviting coffee shops, immerse yourself in its inspiring art galleries, or stroll through unique shopping districts to find one-of-a-kind treasures. Finish your day with a memorable meal at one of Portland’s renowned restaurants—there’s something for everyone to enjoy, no matter the season!
Ready to plan your stay on Peaks Island?
Our summer rentals are now open for booking! Experience the tranquility of island life while staying close to Portland’s wintertime magic. Book your getaway today and start planning a Maine vacation you’ll never forget!
Book your stay with us now and experience the best of both worlds—on Peaks Island and beyond.
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