Portland, Maine, captivates with its seaside charm and vibrant culture, especially in December when the city dresses in holiday splendor. This month, Portland doesn’t just dazzle with its festive streets and waterfront; it also serves as a gateway to exploring the serene beauty of winter in Maine. For outdoor enthusiasts and those looking to reconnect with nature, embarking on the best hikes near Portland, Maine, reveals a quieter, snow-draped landscape that contrasts beautifully with the city’s festive hustle. These trails offer a peaceful retreat into nature, where the crisp winter air and the gentle crunch of snow underfoot create a tranquil hiking experience. Whether you’re a seasoned hiker seeking a winter challenge or someone looking to enjoy a leisurely stroll surrounded by picturesque views, Portland’s proximity to these trails makes it an ideal starting point for your winter adventure.

A Winter Wonderland in Portland Maine: Exploring the Best of the City in December

Portland Maine is a charming city that is a popular year-round destination for many visitors. But there is something special about the city during the winter season, especially in December. The city comes alive during the holiday season with lights, festive decorations, and a range of events and activities that make it the perfect winter destination. In this blog post, we will take a closer look at the best things to do and see in Portland Maine in December.

Experience the Magic of the Holiday Season

The holiday season in Portland Maine is truly magical, with festive lights and decorations that transform the city into a winter wonderland. One of the best places to visit is the Portland Downtown District, where they have a Christmas tree lighting ceremony that includes live music and performances. The Old Port, in particular, is a great area to explore with numerous shops, cafes, and restaurants decked out with holiday decorations.

Celebrate at the Annual Merry Madness Pub Crawl

December is also the time for the annual Merry Madness Pub Crawl, which takes place in the Old Port district. This event is a fun way to get into the holiday spirit and celebrate with friends and family. The event includes a map to various participating bars and restaurants, along with a festive holiday shuttle to take you around.

Go Ice Skating with a View

One of the best things to do in Portland during the winter months is to go ice skating with a view. The city has a beautiful outdoor ice rink in the Old Port that offers stunning views of the harbor. It’s a great activity for families or couples to enjoy.

Take a Winter Walk in the Park

The city also has several parks that are worth exploring, especially during the winter season. The Eastern Promenade is a popular destination, offering breathtaking views of Casco Bay. The park also has well-maintained walking trails that make for a scenic winter walk. Other parks worth visiting include the Deering Oaks Park and the Fore River Sanctuary.

Warm Up with Delicious Comfort Food

After a day of exploring, there’s nothing better than warming up with some hot, delicious comfort food. Portland is known for its food scene, with a wide variety of restaurants and cafes to choose from. During the winter season, many restaurants offer warm, hearty dishes, such as seafood chowder, lobster bisque, and mac n’ cheese, that are perfect for a cold winter’s night.

Additional Information

There’s no doubt that Portland Maine is a destination that should be on everyone’s travel list, especially during the winter season. With all the festive events and activities, stunning winter scenery, and delicious food, it truly is a winter wonderland. Whether you’re looking for a family-friendly outing or a romantic getaway, Portland Maine has something for everyone in December. So bundle up, and come experience all that this charming city has to offer this winter!

Go Ice Skating – In December, Portland transforms into a magical winter wonderland, and what better way to embrace the snow than by spending an afternoon or evening ice skating? You can enjoy skating at the Thompson’s Point skating rink, which is open for general admission to the public. A perfect activity to warm you up during the chilly season.

Visit the Portland Museum of Art – If you’re looking to warm up indoors, take a trip to the Portland Museum of Art. In December, the museum features a variety of exhibitions that will educate and entertain you. It’s a great way to spend a cozy afternoon away from the cold and snow.

Have a Hot Chocolate – During winter, enjoying a hot chocolate comes under the category of “must-do”. Visit one of Portland’s many cozy cafes like Tandem Coffee, Goldenfox Tea, or Boulangerie to relish a warm cup of hot chocolate.

Attend Holiday Festivals and Parades – Festivals and parades are a hallmark of holiday celebrations in December. From tree lighting events to the Brunswick Downtown Association’s Annual Holiday Lighting, there’s always something to keep you entertained in the city during the season.

Explore the Maine Breweries – Portland, Maine is often referred to as the “Beer City” because it has more breweries per capita than any other state in America. The winter season is also the perfect time to explore Maine’s breweries and cozy up while trying their hot, seasonal drinks.


December marks the start of the winter season, and while Portland, Maine is often thought of as a summer destination, winter activities are just as fun and exciting. From visiting the stunning museums, enjoying ice skating, enjoying warm drinks at local cafes and exploring the multiple breweries, the city has something for everyone. Plan your trip to Portland and explore these activities during the wintertime, and you will undoubtedly have an unforgettable and festive experience. Happy Holidays!