Portland, Maine is a city that’s known for its picturesque views and beautiful beaches.
You’re sure to find yourself in awe of the breathtaking scenery while on your Portland vacation. The city’s location near the ocean makes it a great place to go whale watching or just enjoy some time on the water. You can also take advantage of all the hiking trails and scenic views that are available in the area.
If you’re looking for things to do during your winter vacation, there are plenty of museums and theaters in Portland where you can catch a show or learn about Maine’s history. If sports are more your thing, then you’ll be happy to know that there are many sports teams in Portland that include basketball, football and hockey teams.
With so much to do during your Portland vacation this winter season, it’s hard not to have fun!
Portland maine winter vacation
Sip an adult beverage in an outdoor ice bar
I’m not a big fan of being cold, but I make exceptions for ice bars. And since we don’t have them in Atlanta where I live, they are really a treat.
You may think with winter temperatures in Portland, Maine, hovering around from the mid-teens to the lower 30s, your thoughts may turn more to hot teas and hot toddies, but then you’d be missing out on all the frozen fun.
If you’re visiting in January or February, check the dates for seasonal ice bars. I would love to visit the one at the hotel where we stayed, Portland Harbor Hotel, which takes place in January. You can sip on a frosty cold martini while checking out huge ice sculptures. This fabulous hotel offers specials for stays for the Ice Bar, but book early.[See related story: Portland Harbor Hotel in Maine Features Best Location, Restaurant]
Travel just a little ways outside of Portland and you can visit the Ice Bar at Brunswick Hotel. You’ll find ice bars, sculptures and drinks served through ice luges.
Take a lighthouse tour
You can’t return from a trip to Maine without photos of lighthouses. Next to eating lobster, seeing a lighthouse is one of the top things to do in Portland, Maine. There are six lighthouses within 20 minutes and you can see all of them within two hours. Go on a winter weekend and you have the advantage of taking photos with snow in them, one of the cool things to do in Portland in the winter.
These include the oldest operating lighthouse in Maine and the symbol of the city, the Portland Head Light, built in 1791. Just south of Portland is Two Lights State Park, named after two Gothic towers captured by Edward Hopper in his 1929 painting “The Lighthouse at Two Lights.” One of the towers is still a lighthouse, although not open to the public, and the other is a private home.
My favorite is the Bug Light, so called because of its small size of only 26 feet tall. Its official name is Portland Breakwater Light and it’s the only lighthouse modeled after a Greek monument.
The easiest way to see several lighthouses is to take a tour, like the Portland Maine Winter Lighthouse & Waterfront Tour. Visit three lighthouses, learn how the lobster industry works and stop for coffee and a treat at Rwanda Bean.
For a combination tour of the city of Portland and the lighthouses, take the Portland Maine City and Lighthouse Tour.
Bundle up for some outdoor fun
Among the more exhilarating things to do in Portland, Maine, in the winter are outdoor activities like ice skating, dog sledding, cross country skiing, snowshoeing and snowmobiling.
Cross-country skiing is really popular here, with miles of trails in state parks and other trails in the greater Portland area. Pineland Farms in New Gloucester, about 30 from downtown Portland, is a popular excursion for its 30 kilometers of trails for Nordic skiing and snowshoeing. You can also skate and sled here. Check out the views of Mountain Washington in New Hampshire. It’s also a good place to pick up gifts made in Maine.
If snowmobiling is more your speed, you’ll find more than 14,000 miles of snowmobile trails in Maine along with snowmobiling resorts where you can find lodging, equipment rental and guided tours.
Strap on your skates and head to The Rink at Thompson’s Point where you’ll find a warming room, heated lounge, skates for rental and views of Portland. If it’s cold enough, you can skate in parks, on Deering Oaks pond and Mill Creek Park.
No matter what the weather, public skating is available at the William B. Troubh Ice Arena where you can also get lessons and have your skates sharpened.
Sample local cuisine, learn history on a walking tour
While some tours with Maine Foodie Tours are seasonal, operating May-October, a few operate all year. The flagship tour, Old Port Culinary Walking Tour, is available every day and visits several venues for samplings that may include Maine craft beer, fresh lobster, seafood chowder and dark chocolate truffles.
The “Bon Appetite” Culinary Walking Tour takes place in the East End of Portland and includes the city’s newest restaurants along with a taste of the “butteriest croissants.”
You can also take Walk Through Time in Portland history tour that’s given year-round. Sites may include the famous lobster statue, the U.S. Customs House and the home of Henry Wadsworth-Longfellow.
Watch a boat parade along the waterfront
One of the most fun things to do in Portland, Maine, in winter is to view the Parade of Lights when boats are decked out with Christmas lights and cruise along the waterfront in December. Lucky for us our annual visit coincided with the annual event and we walked to the waterfront to get a good view.
The weather didn’t do us any favors. Although the rain held off, the dense fog kept us from getting great views of the passing boats as their decorative lights were shrouded in the heavy mist.
Visit a historic home, museum, or artist’s studio
The Portland Museum of Art has a sculpture garden, film screenings and more than 18,000 works of art in its collection. Highlights include oil paintings by Mary Cassatt, Jasper Johns and Renoir, and an etching by Winslow Homer. You can book tickets here to tour Winslow Homer’s studio in Prouts Neck, where he lived and worked from 1883 to 1910.
Be sure to visit the gift shop, where you can find loads of gifts under $50.
If you’re traveling with kids in tow, check out the Children’s Museum and Theatre of Portland. It’s been named a top museum for children and has interactive exhibits and daily activities.
I love to visit house museums and just happened to notice the Victorian Mansion on a map of downtown Portland. It was an easy walk from Portland Harbor Hotel and as we visited in December, it was completely decked out for Christmas in full Victorian array.
The large brownstone home was built in 1860 as a summer home for hotelier Ruggles Sylvester Morse. It’s considered one of the finest examples of an Italianate brick-and-brownstone home in the United States.[Please note: The mansion is closed from mid-January until May, when it reopens for guided tours.]
For cutting edge work by local, national and international artists, check out the Institute of Contemporary Art at Maine College of Art.
The Art Gallery at the University of New England has six exhibits a year, from contemporary art to photography along with a permanent collection.
More museums to explore in the West End include the Maine Irish Heritage Center and the Museum of African Culture.
Find locally made, unique gifts in boutique and shops in the Old Port area
You’ll want to wear your walking shoes to navigate the sloping streets and cobblestones as you wander around the shop-and-restaurant filled areas of Old Port. I toured on my own one morning and then spent a wonderful afternoon with one of my college roommates, Laurie, who lives in Portland and pointed out some of her favorite places.
This is my favorite kind of shopping, wandering in and out of interesting boutiques and local shops finding goods by local artists and foods by local purveyors.
I picked up a few things for my kids for Christmas, including some awesome pearl earring made by a local artist for my daughter and a cowbell for my son.
I loved the jewelry at Se Vende Imports and couldn’t resist two waxed cotton farmers market totes at Rough & Tumble, a gorgeous leather goods job where I could really put a dent in my wallet.
We took a break for delicious tea and hot chocolate at one of the many local coffee shops downtown.
Take the train to see the giant shoe, go outlet shopping in Freeport
For a fun day trip from Portland, you can take the Downeaster train from the Portland Amtrak station to Freeport, Maine, in around 30 minutes. Freeport is packed with outlet shops, with the most famous being the top-rated L.L. Bean flagship store. You’ll know you’re there when you spot the 16-foot-tall boot out front. It’s a size 410 in case you’re wondering.
Stroll through on your own or ask one of the cheerful store clerks where to find those lobster plates or duck decoys you just have to have.
More than 3 million visitors make their way to the multi-level store each year, which has no lock on the front door as it’s open 24/7.
Load up on lobster
While some versions of lobster rolls have migrated down south where I live, they aren’t quite the same as the truly authentic versions available in Maine.
For our first lobster dose, we walked down to a place I’d been on a previous trip – Eventide Oyster Co. I remembered that their rolls weren’t swimming in mayo, but rather the tender lumps of lobster were held together by browned butter and served on an Asian bun. Hardly a calorie saver, but oh, that flavor.
While the squash blossoms didn’t live up to my memory of them, and seemed exceedingly overpriced, we enjoyed our lobster rolls.
Travel tip: Eventide ships its famous lobster roll anywhere in the country!
Other places for lobster rolls include Luke’s Lobster, Lobster Shack at Two Lights, Scales and The Highroller Lobster Co.
Our next lobster indulgence was at dinner at Blue Fin at Portland Harbor Hotel, where my husband, Chris, helped me attack a whole lobster. It was yummy and served in the traditional way with a potato and corn on the cobb.
The most decadent may have been the lobster stuffed with flounder I devoured at Porthole Restaurant & Pub, down on the waterfront, where we met Laurie for Sunday brunch. We sat by a roaring fire to ward off the December chill. Porthole is also known for its twin lobster dinner special.
If you visit Portland in early March, look for dates for Maine Restaurant Week when you can select from several participating restaurants for prix fixe meals for lunch and dinner.
Down a pint at a local brewery
I’m not a big beer drinker, but if I want my husband’s eyes to light up, I point out local breweries where he’s always up to try a new brew.
And how they love their beer in Maine. If you’re touring the state, get the Maine Beer Trail Passport with more than 100 breweries on it. Visit enough of them and you get a prize like a hat or a T-shirt.
Portland has more than 22 on the list, which include Rising Tide Brewing Company, Bissell Brothers, Allagash Brewing Company and Lone Pine.
Or make it easy on yourself and book a tour with the Maine Brew Bus, which offers several tours on big green school buses.
I want to try the Curling & Brew Tour. During this half-day tour you learn to curl at the Portland Ice Arena, then visit two breweries. Maybe I’ll discover a hidden talent and it’s not too late for my Olympic career after all.
Wine drinkers are totally left out. There are a few tours that include beer, mead and wine while there’s also one just for wine drinkers.
Treat yourself to fresh-baked goods
Continuing his mission to find the best almond croissant everywhere he went, Chris was ready to check out what we could find in Portland at the local bakeries. We made our way to the much-beloved Standard Baking Co where co-owner Alison Pray was nominated for a James Beard Award for outstanding baker. Chris gave the seal of approval for their almond croissant.
Others we didn’t make it to include Two Fat Cats, Bam Bam Bakery and Katie Made Bakery. And don’t forget a trip to The Holy Donut where you’ll have a choice of 16 flavors of donuts.
Take in a performance
The arts scene is big in Portland and no matter when you visit, you can find a performance of some type going on.
Catch a show at Portland Stage, Maine’s largest professional non-profit theater. It has two theaters and affiliate artists events.
Housed in a historic building, State Theatre is a performing arts center with programming almost every night.
The Portland Symphony Orchestra has been recognized as one of the top symphonies for its size in the country and the Portland Ballet is Maine’s professional ballet company.
If improv is your thing, check the schedule of The Fresnel Theater, which also hosts variety shows.
Portland Ovations hosts dance, classical music and other types of live performances.
Take a ferry ride
You can still get out on the water, even in the winter. For something unique to do in Portland, explore the islands of Casco Bay by taking a ferry ride with Casco Bay Lines. Ferries run every day of the year to Peaks Island, Little Diamond Island, Great Diamond Island, Long Island, Cliff Island and Chebeague Island.
A ferry ride is also an excellent way to view several lighthouses. While there are shorter rides, for a view of all the islands, take the 3.5-hour mail run ride that includes some narration if there are more than 10 tourists and stops that may last up to 15 minutes. There’s a heated indoor area if you get too cold.
Destress at a spa and tea lounge, or take a float
When I travel I walk for miles. And that’s just to get through the Atlanta airport! I add thousands of steps to my FitBit when I’m out of town and there’s nothing like a good foot soak to rejuvenate me. Sign up for a foot soak at Soakology and you’ll get sink into a comfy armchair with a warm neck wrap. Enjoy a hot mug of tea from the extensive tea list and a treat from the lounge menu, like Russian tea cakes, macarons or four feet of chocolate, crostini topped with dark chocolate and sea salt. Yum!
If you’re up for a full-body soak, book a float at Float Harder Relaxation Center. Strip down and you’ll have a private float in a pod or float room, complete with your choose of lighting or music.
Adopt a dog from a historic inn
It’s one of the most charming inns I’ve ever stayed in. The Inn By the Sea, a short drive from downtown, features 61 guest rooms and a mile of beach. This inn really won my heart when I learned about its dog adoption program.
While I wasn’t able to take a new friend home with me, I did take the opportunity to take Caldwell out for a frolic on the expansive front lawn.
Free Things to Do in Portland, Maine, in Winter
• Stroll around the waterfront. Commercial Street has two personalities: the vegan restaurants, hotels and cute shops on the city side, and the working waterfront on the water city, Portland’s “working waterfront.” Here you’ll find boat repair shops and fish processing facilities interspersed with a few seafood restaurants.
• Go sledding. If there’s snow on the ground, find a sled and make your way to the slopes in Payson Park and Eastern Promenade for hours of downhill adventure.
• Visit the Portland Museum of Art on Friday when there is free admission from 4-8 p.m.
• Wander through Fort Williams State Park. This 90-acre park is on Casco Bay and features a children’s garden, Cliff Walk and views of Portland Head Light lighthouse.
• Explore art galleries, museums and studios during a First Friday Art Walk, held from 5-8 p.m. the first Friday of every month.
• Attend a Gallery Talk or Artist Lecture Series at the Institute of Contemporary Art
• Stroll or drive through West End, one of the best-preserved areas of Victorian homes in the country.