The Best Things to Do in Portland, Maine in the Winter

Don’t let cold temps scare you away. Portland, Maine is becoming more of a year-round tourist destination, but you’ll still get a more live-like-a-local experience in winter, plus the benefits of lower hotel prices and smaller crowds.

By: Laura James

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Photo By: Laura James

Photo By: Courtesy of Bissell Brothers

Photo By: Laura James

Photo By: Portland Press Herald

Photo By: Laura James

Photo By: Portland Press Herald

Photo By: Laura James

Heading North for Winter

Portland, Maine is known for lobsters and lighthouses, and you can have both in the winter but without waiting in lines to get into the best restaurants or struggling to strategically crop crowds out of your lighthouse photos. For having a population of only about 66,000 people, Portland has a lot to offer in terms of arts and culture. Some locals jokingly refer to their culture-filled city as Portlyn, suggesting their city is the Maine equivalent to Brooklyn, what many consider the hippest of the five New York boroughs.

Check in at a Cozy Boutique Hotel

Sometimes Maine’s winter weather calls for a night in, so stay at a boutique hotel where you don’t even have to walk outside to get a craft cocktail. At The Press Hotel, part of Marriott’s Autograph Collection, you can stay warm and well-fed in the center of town in the former Portland Press-Herald’s office, where every detail honors the story of the building’s past. You’ll find literary quotes on the walls. Guests can unwind at the “Off the Record” happy hour at the Inkwell bar. If inspiration strikes, write a message on the typewriter in the lobby. A permanent art installation called “The Swarm,” made up of vintage typewriters in a not-perfect circle formation, covers a large wall in the lobby to mimic the “organized chaos” often found in newsrooms. Newspaper clippings line the plates at their restaurant Union, which is open to non-guests and has its own separate entrance as well. With Chef Josh Berry, winner of Maine Restaurant Association's 2017 Chef of the Year, at the helm of the kitchen, Union offers regional dishes with locally sourced ingredients. You can’t go wrong with anything on the menu, but don’t pass up the crispy Brussels sprouts.

Check in at a Cozy Boutique Hotel (continued)

Located in a renovated historic home in the West End, The Francis, named after architect Francis Fassett who designed the home for a merchant named Mellen E. Bolster in 1881, is one of Portland’s newest boutique hotels. The building sat vacant for more than a decade before restoration began in 2016, which preserved beautiful details like hardwood floors, tiled fireplaces and stained glass, landing the 15-room hotel on the National Park Service’s Registry of Historic Places. You can also get your drink of choice here without stepping outside the hotel. Bolster, Snow and Co., the restaurant located to the right of the entrance, offers a seasonally-focused and locally-inspired menu with Chef Nicholas Verdisco leading the food and beverage program. The dish of carrot fries, served in a stacked formation that resembles Jenga with a curry mayonnaise for dipping, is a customer favorite. The service is excellent, the atmosphere relaxed and the décor simple, allowing the historic details of the building to stand out. Be sure to check out Tandem Coffee across the street during your stay, too.

Eat Your Way Through Town on a Foodie Tour

If you haven’t heard, Portland is a foodie city, thanks in part to its close proximity to the culinary talent and resources of large cities like Boston and New York. There’s a lot of ground to cover when it comes to the food scene. If you want a custom experience, check out Maine Foodie Tours, where their knowledgeable and friendly guides will take you to some essential spots, highlighting staples as well as new and noteworthy ones. A favorite from my tour was a stop at the Public Market House, a food hall in Monument Square, where I thoroughly enjoyed a taste of blueberry sticky rice made with Maine blueberries from Sticky Sweet, a plant-based creamery and rice shop. If you’re looking for something specific, guides from Maine Foodie Tours will also be able to give great recommendations for other food and drink spots that you can check out during the rest of your stay.

Then Eat Some More

Beyond an organized tour, there are so many restaurants to explore on your own. Some classic go-to spots worth visiting are Eventide for oysters, Otto for pizza and The Holy Donut for doughnuts, which are actually made with Maine potatoes. Pro tip: Order the chocolate sea salt. Opened in 1996, Fore Street is a local favorite for a nice dinner and one of the restaurants that pioneered the farm-to-table movement in the region. Some tourists might miss Woodford F&B since it’s not in the Old Port, but they shouldn’t. Located just off the downtown peninsula in the Woodford Corner neighborhood, Woodford F&B offers thoughtful regional fare in a midcentury modern space that nods to the building’s beginnings as a former steakhouse called Valle’s. You can’t go wrong with the burger (pictured). Other local favorites to have on your radar are Central Provisions, Duckfat, The Honey Paw, David’s, Chaval and Little Giant.

Don’t Forget the Drinks

Portland has developed a reputation for their craft beer, too, with Bissell Brothers, Rising Tide Brewing Company, Shipyard Brewing Company and Allagash Brewing Company being some favorites. Blyth and Burrows has one-of-a-kind craft cocktails, an intimate atmosphere that honors the city’s seafaring heritage and a surprise behind a bookcase in the back: a speakeasy that’s the type of bar other local bartenders go to drink when they get off work. Speaking of speakeasies, there’s a more under-the-radar spot called Lincolns, where all the drinks cost – you guessed it – $5. You’ll have to ask a local for its exact location. In the mood for a wine tasting? Check out the Cellardoor Winery at Thompson’s Point, a mixed-use center with restaurants, shops and an outdoor venue for open-air concerts in the summer and an ice skating rink in the winter. For coffee, stop by a Coffee by Design or Tandem Coffee location.

See More: The New Top 10 Beer Cities

Go Shopping in Freeport

The flagship store of L.L. Bean, the outdoor gear company that created the OG bean boot, is hard to miss in the charming town of Freeport, located about 20 minutes from Portland. The store opened in 1917 and they went 24/7 in 1951, only closing a couple of times since for major family events. Beyond L.L. Bean, there are several other outlet stores in Freeport to score some deals, plus the most charming McDonald’s you’ll probably ever see; it’s in a Colonial-style home with modest signage. After you’ve worked up an appetite shopping, grab lunch, or even just afternoon tea, at the Harraseeket Inn. Spending a day in Freeport is a great option when the weather isn’t cooperating.

Work Up a Sweat on the Trails

If the weather is cooperating, take advantage of L.L. Bean’s Discovery School and work up a sweat on the trails. Try your hand at cross-country skiing or snowshoeing with the help of their knowledgeable guides to make it a great experience for even the most beginner of athletes. While Portland is definitely a foodie town, it’s also an active city that loves the outdoors. So all those calories we recommended you eat? It’s fine; you can work them off in no time.

Visit the Portland Museum of Art

For being a smaller city, the Portland Museum of Art has quite an impressive collection but lacks something art museums in larger cities have – the crowds. You can zip through in 20 minutes or take your time and spend an hour or more staring at Winslow Homers in a more intimate setting. The PMA is free Fridays from 4 p.m. to 8 p.m., and if you visit on the first Friday of the month, be sure to pop in other local galleries and shops for the city’s First Friday Art Walk.

Play and Learn Inside the Children's Museum

This photo looks like it’s from a tiny house or yurt camp, but it’s actually a cool, cozy reading nook at the Children’s Museum and Theatre of Maine, where everywhere you look there’s a creative corner or colorful, interactive exhibit. Entertain the kiddos for a few hours at this museum that focuses on hands-on learning and discovery through exhibits like Lights, Camera, Color: Exploring the Camera Obscura, where kids can interact with a real periscopic camera obscura; Our Town’s Farmers’ Market, where they can practice math skills and learn about Maine’s local food movement; and Fire Truck, where kids can “drive” a 25-foot fire truck and slide down a brass fire station pole – a favorite spot at the museum.

Catch a Concert

Another surprising thing about Portland for its size is the amount of music and theater performances they have, including its own symphony. Catch the Portland Symphony Orchestra in concert, or even Broadway performances, at Merrill Auditorium (pictured). The historic State Theatre is another place to catch popular bands. For spontaneous live music, pop into a smaller venue like Blue for lesser-known, often regional acts.

Ferry to Peaks Island

Make time to visit at least one of the islands in Casco Bay like Peaks Island. Take the 17-minute passenger ferry out for only $4.10 during the off-season or $7.70 during peak season. While many of the ice cream shops and restaurants close for the winter months, you can still walk around and take in the gorgeous ocean views.

See Lighthouses in a Different Light

When you picture Maine’s charming lighthouses against its rocky coastline, you’re most likely imagining them in the summer, but have you seen Portland Head Light with a dusting of snow? It’s pretty spectacular. Plus, overcast days are exactly the ones for which lighthouses were intended. Either drive yourself or book a tour with a local company like Maine Day Trip Tours out to the Portland Breakwater Light (also called Bug Light) and Portland Head Lighthouse in Cape Elizabeth to glimpse some of the most iconic scenes in the area. These lighthouses are crawling with tourists in the warmer months, but if you visit in winter, you can mostly count on crowd-free photos.