Tommy's Park - Portland, Maine
· · ·

10 BEST Winter Things to Do in Portland Maine This Year

Portland Maine is one city that doesn’t flinch at the change of any season. As the biggest city in the state, everyone from the lobstermen to the lawyers keeps chugging along — usually with the best brews of each season after work.

Winter in Portland Maine offers a smorgasbord of activities that might fall to the bottom of the list when the beach is calling in summer. Plus, the winter climate paints a unique canvas — from the lighthouses to Old Port.

Despite being one of the “milder” locations for winter in Maine, Portland still picks up about an average of 5 feet of snow. What a great excuse to order a second bowl of chowder! Here are the top 10 things you can explore during winter in Portland Maine.

NOTE: “Winter” is a subjective term across Maine. Expect “winter hours” to last into April or May for some attractions, tours, and locations. So, you might think that you’re taking a spring trip to Portland when you’re really visiting during “mud season,” the moniker for spring in Maine. That’s also a great time to take a day trip from Portland to one of the ski resorts in the mountains.

The Rink at Thompsons Point Portland Maine Corey Templeton
The Rink at Thompson’s Point | photo via Corey Templeton

Visit During Carnaval

Portland is home to Carnaval Maine, a winter festival that mixes fire, ice, igloos, and adventure. Live ice sculpture-making takes center stage outside, while the covered stage brings comedy and musical acts to perform throughout the days of the festival.

Come hungry, too, because you’ll sip and savor some of the best creations from local restaurants and breweries.

Skate on Thick Ice

Embrace all the benefits of a cold winter with ice skating locations from Thompson Point with Fore River Views to Deering Oaks where Whitney Houston and Denzel Washington skated while filming “The Preacher’s Wife.”

The Parks and Recreation Department regularly maintains several other ponds in Portland because safety is paramount. They update the conditions on Facebook and have signs at each spot detailing ice thickness.

Grab Your Sled

When a good snow base comes, it’s time to go sledding at one of several picturesque locations around Portland. The Eastern Promenade is a great first choice because you’ll have Casco Bay views as you slide.

On the other side of the bay, Payson Park has a popular hill with plenty of space for everyone. A skating pond and ski and snowboard terrain park are open here as well. You’ll find rails, hills, and boxes at the terrain park.

At Riverside Golf Course, winter tees off a slew of activities, including all those golf course hills for sledding and trails carved for skis or fat tire bikes. As a bonus, it’s open 24/7. Even the skating rink has a light.

Freeport, Maine
Freeport, Maine | photo via @zoebabian

Ski the Back Bay & Beyond

When you want more rugged conditions for cross-country skiing but don’t have the time (or inclination) to drive into the mountains, Portland is ready for you.

More than half a dozen locations are designated around the city, including Baxter Woods and Western Promenade. The cross-country trails will give you more of a backcountry experience, but that comes with more potential hazards under the snow.

In nearby Westbrooke, look for the hours and conditions at Smiling Hill Farm. And, expand your options with the Presumbscot Regional Land Trust winter trails.

To explore other towns in the region, ski, walk, or bike the Eastern Trail, which starts in Portland and stretches all the way to Kittery Maine. It spans 65 miles each way.

Walk Through History

Portland Maine is filled with landmarks, and learning all the neighborhoods can be daunting. Thanks to the team at Greater Portland Landmarks, you can customize a self-guided tour — from Portland’s numerous districts to Gorham or Yarmouth. Meanwhile, Maine Day Adventures offers guided tours throughout winter.

Just south of the Eastern Promenade, you’ll find historical markers and memorials at Fort Allen Park. There’s another fort just offshore in Casco Bay. See if you can book a private winter tour, especially if you catch a few days of mild weather. Fort Gorges was built in 1864, but never saw a battle — or a soldier, for that matter.

You’ll have a hard time avoiding Monument Square, but there’s a spectacular Civil War Memorial in the heart of the city.

Winter Closures: Wadsworth-Longfellow House tours stop from October until June, and Victoria Mansion is closed after the holiday event in December and early January until May.

Portland Museum of Art
Portland Museum of Art | photo via Canva

Tap Into Your Artistic Side

For every lobster pulled from Casco Bay, there’s an artist in Portland, making this a diverse stop for winter sightseeing. The First Friday Art Walk goes on through the winter months, and you can download the Creative Portland app to get an inside look at all the creative stops.

The mothership of creativity is the Portland Museum of Art. With a collection of 18,000 pieces of work spanning New England’s landscape — from painting legend Winslow Homer to Monet — you could easily fill an entire day and still not see it all here. New exhibits come and go, so you’ll get a new experience with each visit to Portland.

Another great art stop is the Maine Museum of Photographic Arts.

Traveling outside of Portland? Consider other stops on the Maine Art Museum Trail, spanning 350 miles through nine museums.

Take a Ferry Ride

Commuters from across Casco Bay use the ferry to get to Portland, and that’s a year-round bonus for tourists. In fact, you can get to Peaks Island, Chebeague Island, Cliff Island, or any island with the word “Diamond” in it.

The winter ferry schedule runs through mid-April, with departures as early as 6 a.m. and as late as 10 p.m. Leashed dogs and bicycles can come aboard with an extra ticket. Even if you just ride the ferry out and back, it’s still one of the best value boat tours any time of year.

Also, check out the Mailboat Run specialty cruise. You ride on the same boat that takes all the mail and shipments to the islands. If more than 10 people are aboard, you’ll get narration along the way.

Children's Museum & Theatre of Maine-Portland
Children’s Museum & Theatre of Maine | photo via abbyopearson

Enjoy Portland’s Museums

Plenty of museums stay open in the winter. As a quick travel tip, most museums are likely to be closed on Mondays and/or Tuesdays.

The Children’s Museum & Theatre of Maine is now at home in Thompson’s Point (next to the skating rink). The museum is designed to spark the imaginations of children of all ages with theatre productions and classes available throughout the season. With three stories to explore, you’ll learn about art, science, math, and cultural diversity.

The Maine Historical Society Museum closes in January but is open all other months of the year. Rotating exhibits bring new stories of Maine’s history to the forefront, and you’ll be able to see the Wadsworth-Longfellow House Garden while you’re here.

Holy Donut-Portland
Holy Donut | photo via ctcoffeeandcarbs

Eat Your Way Through Maine Specialities

First, you need a checklist of all the Maine delicacies. It might help to pair this list with the Best of Portland Maine winners.

Start your day with a famed Maine potato donut at The Holy Donut. (Did you know that potatoes are a half-billion-dollar business in Maine?) And while not all lobster shacks are open in winter, local favorite J’s Oyster stays open with heaping doses of lobster in rolls, chowder, and mac and cheese. Try the Crabby Janice to get started.

An exquisite way to enjoy a winter meal in Portland Maine is in a heated igloo. Look for this fun feature at places like Harbor Bistro & Terrace and Alto Old Port.

Any winter night is perfectly capped at Top of the East, an iconic view 15 stories up with a range of drinks to warm you up while soaking in the views. And, we can’t pick just one favorite brewery (or even three) because there are plenty of options that serve winter specialties. So, check out our full guide to Portland Maine breweries.

NOTE: We understand the expansive Portland food scene can make it hard to pick the right spot, so consider a Food & Beverage Tour of Old Port.

Portland Head Light-Cape Elizabeth
Portland Head Light | photo via thisplaceinmaine

Go On a Lighthouse Lookout

Let’s be honest — lighthouses were built to guide ships during big storms, a winter staple of New England. Wouldn’t this be one of the best times to see the waves crashing at the base of these mighty marvels? (Rhetorical question. Of COURSE, it would!)

Head to South Portland (SoPo, as it’s known) and Cape Elizabeth for some of the most popular lighthouses in the state. Contrary to what some might think, the Portland Head Light is actually in Cape Elizabeth — the name comes from the “head of land” it sits on. The lighthouse is within Fort Williams Park, which is open from sunrise to sunset, and several scenic viewpoints are available within the park.

TIP: For the best winter sunrises, hop aboard an early ferry or bundle up at the East End Beach. Watching the sun set over Portland from Peaks Island is a pretty spectacular way to end a winter day too.

Two Lights State Park and Bug Light Park offer more lighthouse views. One of the best winter lighthouse experiences in Portland Maine comes at the end of a 500-foot breakwater. Spring Point Ledge Lighthouse takes some careful footing to reach, but the views of Portland, the Portland Head Light, Fort Gorges, and Casco Bay islands are worth it.

Tommy's Park - Portland, Maine
Tommy’s Park | photo via @grossconfectionbar

Add These Winter Things to Do in Portland Maine to Your Getaway Itinerary

With so many winter things to do, you won’t even notice the cold weather in Portland Maine. From ice skating to ferry rides to museum tours, the activities abound for all skill levels and interests. You can even head to one of the spas at The Longfellow Hotel and The Francis if you just want to relax and chill.

Did we miss your favorite Portland Maine winter activity? Tell us in the comments!

Similar Posts

Leave a Reply

Your email address will not be published. Required fields are marked *