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13 Cool and Cozy Things to do in Portland Maine in the Winter

Lighthouses, lobster, boats bobbing on the Casco Bay, waves crashing against the rocky shore. This is what we typically think of when we think of Portland, Maine. Although we usually picture that scene under the warmth of the summer sun. Well, you can still find that natural beauty in Portland Maine in the winter, it just may be a little chillier, icier, but also quieter.


Fishing boats on the wharves in Portland maine

I’ve visited Portland Maine well over a dozen times in the last decade — always in the summer. It took me until recently to take a getaway to Portland in the winter and I was pleasantly surprised to find I loved this coastal city just as much in the cold. If you are wondering whether or not to visit Portland in the winter, let me give you some reasons why:

  • The hotels are sooo much cheaper! When we used to need to stay in Portland during busy summer weekends for summer camp drop off or pick up, I’ve seen hotel rooms (and I’m talking about standard chains like Courtyard by Marriott) go for up to $1,000 a night. Winter rates are a totally different story. You can find nice hotels midweek for about $100 per night and under $200 a night on the weekend.
  • Finally get those restaurant reservations. Portland is known as a food city with an incredible restaurant scene. Sometimes getting into those restaurants can mean booking reservations the minute the system opens or waiting in long lines for walk in spots. Winter is the ideal time for trying some of those hard to get into restaurants. Yes, a few close for the season, but many aren’t just focused on tourists and are open year round.
  • Enjoy Old Port without the crowds. Summer brings cruise ships to Portland and plenty of tourists. The tourism business is great for the city, but it is nice to get to enjoy Portland like a local without the groups of tourists.


Portland Head Light in the winter


Not matter what season you visit, if you have never been to Portland before, you need to stop at Portland Head Light. Located in Cape Elizabeth in Fort Williams Park, just 10 minutes south of downtown, this is one of the most picturesque spots in the Maine. Set on a promontory, it can definitely be windy in the winter and it may not be ideal for a picnic in the park, but at least make time for a photo opportunity and a stroll along the coastline path.


cobblestone street in Old Port

There is a reason why the waterfront in Portland is called Old Port. This area has a 200 year history that covers the American Revolutionary War, Civil War, development of the railroads, women’s suffrage, the temperance movement, and the abolition of slavery. You can easily take a self-guided walking tour of downtown, but to learn more of the city’s history, take a Walk Through Time tour with Maine Day Adventures.

These two hour walking tours cover Maine’s maritime, industrial, and cultural history with a walk through the historic Old Port, downtown and waterfront areas. It covers local architecture, historic buildings, important statues, and an exploration of the Portland Freedom Trail. 


Haberdashery resale thrift shop in Portland Maine

Old Port has its share of boutiques and souvenir shops, but a slew of thrift shops have also cropped up and you never know what treasures you might uncover in a new city. Haberdashery Resale Clothing Co. on Commercial Street is where you will find the best designer threads, but for great deals also check out Find, Material Objects, and Weekend Vintage downtown.

If you are looking for vinyl gems, check out Moody Lords Vinyl/Vintage or Enterprise Records.


Renoir painting at the Portland Art Museum

The Portland Museum of Art has a permanent collection has over 42,000 works of art ranging from sculptures by Rodin to paintings by Renoir. There are also changing exhibits of contemporary and local artists spanning multiple buildings, including the historic McLellan House, a Federal style mansion that was a former ship captain’s home.

For art lovers, this is a perfect place to spend a winter afternoon, although the museum is free every Friday from 4:00 to 8:00 p.m.


I love food tours for exploring new cities and as a foodie city, Portland is prime for it. However, walking around and snacking on sidewalks in the snow is not super fun. Luckily, Maine Day Adventures offers a Winter Warmer Walking Tour, as well as the Old Port Culinary Walking Tour that operates year-round.


Allagash beers

Portland is America’s “Craft Beer Capital” and there are over 25 breweries in the Portland area alone. While the beer tours may not operate in the winter, it is easy to walk to many of the downtown tasting rooms to sample local brews such as Shipyard or Rising Tide.

If you have a car, you can also visit some well-known breweries such as Allagash or head up to Freeport to sample the options from Maine Beer Company.


A winter weekend getaway is a perfect time to cozy up in a spa for relaxation and wellness. You have a range of options in Old Port and Downtown Portland to choose from including Paint nail bars, Maine Aesthetic med spa, and Nine Stones Spa, which is a day spa offering massages, body treatments, skin care, and nail services.

You can also enjoy a foot soak and massage at Soakology, at saltwater float at Float Harder, or sit in a salt room at The Salt Cellar.


Lobster roll from Eventide Oyster Company

Some summer favorites like the Bite into Maine food truck and Portland Lobster Company are closed in the winter, but don’t worry, you can still get plenty of fresh lobster in Portland. One of my favorite spots is Luke’s Lobster, at the end of Portland Pier, offering great water views where you can watch the lobster boats or ferries come and go.

It is also a great time to slide into Eventide Oyster Company without waiting in a long line. This popular spot always has a great selection of fresh oysters, but I’m a sucker for their browned butter lobster rolls served on a bao-style bun.


Casco Bay Soap company

Whoopie pies, blueberry jam, and maple syrup, are just a few things that Maine is known for. But you will also find the flagship store for Maine Seabags, a large gallery and shop from Edgecomb Potters, and a range of other New England brands such as Simon Pearce glassware and Vermont Flannel Company.

In various gift shops and boutiques you will also find soap from the Casco Bay Soap Co. and gourmet foods from Maine Homestead. Take home a little taste of Maine to remember your trip!


dark chocolate sea salt donut from holy donut

One of my must stop places in Portland is Holy Donut. When I first posted on Instagram about their tasty potato donuts I got a lot of confused responses. You probably know cake donuts and brioche donuts, but Holy Donut uses riced potatoes in its recipe, adding a density and deliciousness that I love. Unlike the trendy donuts that have more stuff on top than inside the sweet itself, Holy Donut lets the flavor shine. My favorite is the dark chocolate sea salt (and they also come in gluten free versions too!)


Longfellow Bookstore in Portland Maine

I don’t know about you but I love whiling away a winter afternoon browsing the shelves of an independent bookstore. Portland has its share of options, from the popular Maine chain of Sherman’s Maine Coast Book Shop to Longfellow Books in Monument Square and Print, an indie bookstore that hosts author signings and events.


igloo at the Alto Terrace bar and kitchen

Enjoy winter in an après ski fashion by booking a cozy igloo at ALTO Terrace Bar + Kitchen at the Cambria Old Port. These heated igloos seat up to six and offer ski lodge decor, complete with blankets, and Bluetooth speakers to play your favorite tunes. Drinks and food will be delivered straight to your igloo where you can enjoy a hot toddy, mulled wine, or the cocktail of your choosing.


When you are in Portland, it is really tempting to pop up to Freeport (about 20 minutes north) to shop at the L.L. Bean Flagship store and outlet. And if you are in the market for outdoor gear, Freeport is bursting with other outfitters and outlets including Patagonia. Don’t forget to take a photo with the giant L.L. Bean boot!


Note: My recent stay was hosted by the Cambria Hotel Old Port for purposes of review. All opinions are my own.

Over the years, I’ve stayed all over Portland including many hotels in Old Port such as the Press Hotel, Courtyard by Marriott, Hilton Garden Inn, Westin Downtown, and the AC Hotel. During the time, I have seen the Old Port area expand with new hotels being built each year. It has been great to see this growth of hotel inventory to meet the high demand.

I recently stayed at the new Cambria Hotel Old Port. Cambria is part of the Choice Hotels, with over 60 hotels nationwide, each of which are owned and operated individually. The Cambria is located in the newly-developed eastern portion of the Old Port, just a short walk from the cruise terminal and ferry port. I love the location because you are literally a block from some of my favorite restaurants and not far from Downtown and the Munjoy Hill neighborhood.

Tamara in lobby at Cambria Old Port

The modern hotel has everything you would need including an on-site restaurant, ALTO Terrace Bar + Kitchen, serving breakfast and dinner, which is perfect for when you don’t want to leave the hotel on a chilly winter day! ALTO features the flavors of Maine using locally sourced ingredients along with local brews, handcrafted cocktails, and a signature wine selection. I’d strongly suggest trying the chipotle mussels and the fried Brussels sprouts — both are sooo delicious!

In the winter you can also reserve a cozy igloo on the terrace and when the weather is warmer, the terrace fire pits and a full-service bar.

The rooms at the Cambria are modern and spacious, with locally-inspired decor and amenities like Keurig coffee machines, mini fridges, bedside outlets, and in-room safes. I loved the large shower and the plentiful counter space in the bathroom.

The Cambria also has a full 24-hour fitness room with cardio equipment, weights, medicine balls, dumbbells, and more. If you forget something, there is also a small concession in the lobby and I found the staff always extremely friendly and helpful.

Tamara Gruber

Tamara Gruber is the Founder and Publisher of We3Travel. A former marketing executive and travel advisor, Tamara is an award-winning travel writer and recognized expert in family travel. Tamara is a member of SATW and the Adventure Travel Trade Association, and serves on the Board of the Family Travel Association. She is also the publisher of and the co-host of the Vacation Mavens travel podcast.

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