Best Things to Do in the Winter in Portland, Maine

Many choose to visit coastal Maine in the summer months, so there remains an almost undiscovered charm to Maine’s largest city when it settles into the quiet of winter. The streets clear and the old-school brick walkways and salty air intertwine, every road lacing its way back down to the city’s working waterfront. Each morning, myriad coffee shops offer piping-hot brews and freshly baked goods as commuters begin their chilly walk to work. Independent shop owners open their doors to welcome winter wanderers in from the cold. And when evening comes, Portland offers a seemingly endless number of award-winning restaurants from which to choose.

This is a city which remains alive each winter, despite the arrival of the cold. After all, lighthouses and lobster rolls don’t disappear when the temperature drops. They might even be better – if you’re willing to bundle up, that is. 

Wondering what to prioritize on your next trip? Read on for some of our favorite things to do in Portland, Maine, in the winter!

Note: During the winter some businesses may be closed due to bad weather, winter breaks, or other unforeseen circumstances. We always recommend checking in with restaurants and businesses before making plans, but especially so in the winter!

Best Things to Do in the Winter in Portland, Maine

Shop and stroll through Portland’s beautiful brick-lined Old Port

Mere steps from the city’s maritime roots, with the sounds of the working waterfront still well within earshot, the Old Port provides the perfect place to situate yourself in the city. With lots of hotels close by – including many of our picks for the best hotels in Portland (below) – it would be easy to sleep, shop, stroll, and dine for days all within the bounds of this beautiful neighborhood. Though the crowds will be subdued in comparison to peak summertime buzz, you may be surprised by the number of people: the Old Port remains one the most popular spots in Portland year-round, for good reason.

Walk along the Eastern Promenade and admire Casco Bay

In our summertime guide to spending a weekend in Portland, writer Sara Anne Donnelly perfectly described the layout of the city:

Think of the topography of Portland’s peninsula as a saddle—a hill on either side with the Bayside, Downtown, and Old Port lowlands in the middle. The peninsula is about three miles long and includes the West End, Parkside, East and West Bayside, the Arts District and Downtown, the Old Port, and the East End. This city center is bookended by the Western Promenade and Eastern Promenade parks, both laid out by famed landscape architect Fredrick Law Olmsted, designer of New York’s Central Park.

Here we will focus our attention on the Eastern Promenade, which makes for a particularly wonderful winter walk. This is an activity perfect for unseasonably warm winter days, though many find it equally enjoyable under a few layers. You’ll likely want to drive to one end of the Promenade if the weather is chillier, but braver souls can wander their way to the beginning of the Promenade from the Old Port. From either end, stroll the length of the “prom” and look out to the shining waters of Casco Bay.

Take a brewery tour

With over 25 breweries to choose from, this small-but-mighty city boasts the highest count of breweries per capita in the United States. From craft brewing pioneers like Allagash and Shipyard to young, award-winning upstarts like Austin Street, Batson River, and Oxbow, you could spend days tasting your way through these coastal concoctions and still have ground left to cover.

Visit a museum

The largest and oldest public art institution in Maine, the Portland Museum of Art offers highlights from three centuries of art in its trio of downtown buildings. There’s a top-flight collection of paintings by American realist and impressionist masters (Rockwell Kent, Andrew Wyeth, and Marsden Hartley, to name a few), a treasure trove of fine and decorative arts, and the largest holding of European art north of Boston. Kids will love exploring the animal-themed installation Modern Menagerie and visiting the Workshop, an exhibit space featuring hands-on, interactive activities.

Looking for a museum that appeals to kids and adults alike? At The International Cryptozoology Museum, an 8-foot-tall Bigfoot greets visitors. Loren Coleman, the creator of the museum, is a renowned expert in cryptozoology, the story of hidden animals, such as the Loch Ness Monster and the Abominable Snowman.

Cozy up at a coffee shop

There’s nothing like a steaming hot cup of coffee or cocoa to warm you up on a chilly day, and Portland is home to a number of excellent contenders to choose from. Our favorites include Speckled Ax, Bard Coffee, Arabica, and Coffee By Design.

Experience the magic of live music or theater

When snowflakes fall and temperatures drop, it’s always tempting to hunker down indoors, throw a bag of popcorn into the microwave, and grab the remote. Yet one of the most surefire ways to warm your heart and soul during a long New England winter is by venturing out of the house for a live performance. And while the waterside shows at Thompson’s Point may be off-limits during the colder months, Portland offers many excellent indoor options to choose from. One of our all-time favorite Portland music venues is the historic State Theater on Congress Street, with a beautiful, 1,870-seat Art Deco auditorium which reopened in 2010 after extensive renovations and updates. Many famous musicians have graced its stage, from Brandi Carlile to Bob Dylan.

Enjoy a hearty meal at one of Portland’s many renowned restaurants

Regardless of the season, great food is always nearby in this coastal city. Portland’s culinary accolades have grown exponentially over the last decade, with many of the city’s restaurants winning national awards and catching eyes on top-tier lists. With this media attention, however, has come demand. It can often be tricky to dine out in Portland during peak tourist season, when wait times soar at the most coveted restaurants. Fortunately, it’s much easier to find a table at some of the region’s finest dining establishments in the winter, since fewer tourists means fewer people competing to snag a spot in line.

Many of the restaurants below don’t accept reservations, so it may be best to pop your head in and ask about availability. Waiting for a table? Around every corner sits a cocktail bar, old-school pubs, or breweries where you can sit and wait for your table to free up. If you’re lucky, a few fresh flakes of snow may even fall as you’re making your way back!

What’s your favorite thing to do when visiting Portland, Maine, during the winter? Let us know in the comments below!