Portland, Maine is not just a summer destination but a city for every season. Just within our city limits are ways to cozy up outside with firepits, outdoor dining, and s’mores nights. Go a little further, and our parks and green spaces are a winter wonderland for outdoor recreation, including skating, sledding and cross-country skiing.
With winter underway, check out our full list of ways to enjoy this city this season—whether you’re an avid outdoor enthusiast or simply enjoy a hot beverage in crisp winter air.
Did we miss your favorite way to enjoy the winter season? Send us an email at info@portlandoldport.com, or DM us on Instagram @portlandoldport.
Winter in the City
Winter Outdoor Dining: One great thing to happen in the past few years is the extension of Portland’s outdoor dining scene. Many restaurants have converted their patios into igloos and heated dining spaces. Remain cozy even when outside with fire pits, heat lamps and seat warmers. For a complete list of restaurants ready to brave the cold this season, visit our Outdoor Dining Guide.
S’mores Nights at Congress Square Park (across from the Portland Museum of Art), presented by Friends of Congress Square Park. Featured in downtown Portland again this year, city visitors are invited to enjoy fire pits, s’mores fixings and guest entertainers Thursdays from 4-6 p.m. until February 23, 2023. If the s’mores aren’t enough to get you outside this winter, S’mores Nights also offers food truck favorites (such as The Pink Waffle) and hot drinks for sale. While S’mores Nights are free to the public, a $5 donation for Friends of Congress Square Park is encouraged—or $10 if you want a S’mores Night blanket. For the full food and entertainment schedule, click here.
First Friday Art Walk: Grab your friends and get outside to find new artists and galleries to support this winter! The first Friday night of every month—even in January and February—First Friday Artwalk takes over Congress Street. The lineup of artists and events differ every month; for monthly details, click here.
Carnaval Maine: Portland’s biggest winter party returns March 8-12, 2023—this time by DiMillo’s on Commercial Street in the heart of the Old Port. The music-focused event features headliners The Mallett Brothers Band, Parmalee and Amy Allen. The lineup also includes theater, comedy, a Bites and Brews tasting event (21+), food trucks and lots of family fun (free for ages 10 and under!). For details head here.
Winter Recreation
If you’re looking to play outside, there are winter wonderlands right here in the city of Portland—for activities ranging from skating to cross-country skiing. Before heading out, check the City of Portland’s conditions map that covers five skating ponds, three sledding hills and groomed cross-country skiing trails. When the icon is green, you know you’re good to go.
*A friendly reminder that none of the city parks rent winter gear; see the GEAR UP section below for where to buy or rent skates, skis, snowshoes and fat tire bikes.
Payson Park (Back Cove): Payson Park is a local favorite sledding spot, and the City of Portland maintains an ice-skating rink across from the tennis courts off Catafalque Drive. Payson even has a small ski and snowboard terrain park with rails, boxes and a snowmaking system!
Eastern Promenade: A favorite park of locals and tourists alike, the Eastern Prom is the granddaddy of all sledding hills. Skip work (we won’t tell) for a picturesque snow day on the slope; the Cutter Street parking lot is unplowed to allow for a long and safe runout area.
Deering Oaks Pond (Deering Oaks Park): The Deering Oaks Duck Pond by Queenie’s Castle is vintage postcard perfect. In the crisp clear evenings of winter, light sculptures reflect on the ice and create a warm, inviting glow. Lace up your skates and glide across this classic ice-skating destination. The City clears the snow, but conditions are highly variable because the pond is a stormwater basin.
Ludlow Pond (Deering Center): Deering Oaks isn’t the only classic skating pond in Portland. Ludlow Pond, near Deering High School, has been a neighborhood skating spot for nearly 90 years.
Capisic Park (Capisic Street in Nasons Corner): Capisic Pond is the largest freshwater pond in Portland and home to a variety of bird species. The park is an excellent destination for those willing to brave the cold. Put on your heavy boots or rent a pair of snowshoes to explore the park and give birdwatching a try. You can also skate the pond after a hard freeze. Capisic Park welcomes snowshoes, bikes and dogs on the city-maintained trails.
Riverside Golf Course (1010 Riverside Street): Making great use of their 200 acres, Riverside Golf Course is a must-visit winter destination for cross-country skiing, snowshoeing, fat tire biking, sledding and ice skating. Use of groomed trails is free, with dogs welcome on one of the trails (here’s a map with details).
Presumpscot River Preserve: Offering 60-acres property on both sides of the Presumpscot River is the Presumpscot River Preserve. The Preserve includes 3.5 miles of trails for great for snowshoeing, cross-country skiing and fat tire biking. The easiest point of entry is at Oat Nuts Park trail (park by Lyseth Elementary School on Auburn Street or on Overset Road).
Troubh Ice Arena (Park Avenue): If the weather outside is frightful, the ice surface is always just right at Troubh Ice Arena next to the Expo Center. You can rent skates here or get a skate sharpening. Check their website for reasonably priced public skating hours, Learn to Skate sessions and adult pick-up hockey. Troubh is also the home of Pine Tree Curling Club, which offers Learn to Curl sessions and league play.
Honorable Mention:
The Rink at Thompsons Point: The Rink at Thompson’s Point is closed for winter 2022-2023 for upgrades on the rink infrastructure and other development at Thompson’s Point (including a seasonal dock with access to the Fore River!).
GEAR UP
To really enjoy being outdoors in the winter, you need the right clothing and accessories—and, for many outdoor activities—the right gear. From coats and hats to bindings and poles, you can find it all right here in Portland.
Arlberg Ski & Surf Shop (283 Marginal Way): Ski and snowboard equipment and related services, plus winter apparel.
Allspeed Cyclery & Snow (127 Marginal Way): Allspeed leases and sells ski equipment and does boot fittings, with a focus on backcountry skiing.
Eastern Mountain Sports (EMS) (87 Marginal Way next to Trader Joe’s): EMS sells everything you need for cross-country or backcountry skiing or
snowshoeing.
Play It Again Sports (315 Marginal Way): This second-hand resale shop for sports equipment is a great place for both children and adults to purchase hockey and figure skates, and snowshoes. They carry some new stuff, too, including sleds, snowpants, goggles, helmets, skate guards and hockey gear. And they sharpen skates.
Gorham Bike & Ski (693 Congress St): You can rent fat tire bikes here or shop for snowshoes and all things ski, from alpine to cross-country to roller.
Renys (540 Congress St): Though perhaps not the first place you think of for outdoor recreation gear, Renys sells reasonably priced cold-weather outerwear, plus some gear you never thought of—like trekking pole sets for winter hikes.
Portland Gear Hub (155 Washington Ave): Find a deal on snowshoes, ski equipment, and winter apparel and support a Portland-based nonprofit that helps increase equitable access to affordable, reliable gear—including bikes for Mainers who need them for transportation.
