From sunrise thermos walks to igloos, trivia nights, and wintry beach walks, this list is your invitation to treat February like a month-long micro-adventure. Use these ideas as date nights, solo resets, or ways to show off Portland to visiting friends. Circle a few, add them to your calendar, and let small, local moments brighten even the grayest days here.
- Sunrise Thermos Session on the Eastern Prom
Pack a thermos, walk the Eastern Promenade Trail at first light, and watch the sun rise over the islands while the harbor wakes up.
- Waterfront Igloo at Harbor Bistro + Terrace
Book a heated igloo for a cozy night of creative local dishes and drinks on the edge of the Old Port. harborbistroandterrace.com
- Arcade Night at Arcadia
Warm up with cocktails and old-school games at Arcadia on Congress—pinball, Pac-Man, skeeball, and more. arcadiaportland.com
- Indoor Farmers’ Market Morning on Stevens Ave
Hit the Portland Winter Farmers’ Market on Saturdays for root veggies, bread, cheese, and flowers, then cook a local-love dinner at home.
- Scandi-Inspired Cocktails at Portland Hunt & Alpine Club
Slide into a booth at Portland Hunt & Alpine Club for a wintery cocktail and Nordic-inspired snacks after a cold-night wander. huntandalpineclub.com
- Casco Bay Lines Winter Island Hop
Take a daytime Casco Bay Lines ferry to Peaks or Great Diamond, walk the quiet roads, and sip coffee while watching for sea smoke on a frigid morning. cascobaylines.com
- Washington Baths Sauna + Plunge
Reserve a session for a sauna + cold plunge ritual, then journal how your body and mood feel afterward.washingtonbaths.com
- Back Cove Loop with a Podcast
Walk the Back Cove Trail, a 3-ish mile loop, listening to your favorite podcast—then grab a treat from a nearby bakery.
- Bird Walk & Snowy Fields at Gilsland Farm
Wander the gentle trails at Maine Audubon’s Gilsland Farm with binoculars, or join one of their winter bird walks through meadows, orchard, and salt marsh.
- Journaling Date in a Hotel Lobby
Tuck into the lobby at The Press Hotel or Canopy with a winter drink and spend an hour journaling or writing gratitude lists.
- Frozen Falls Hike to Jewell Falls
Follow Portland Trails into the Fore River Sanctuary to Jewell Falls, Portland’s only natural waterfall, transformed into winter ice.
- Wednesday Trivia at Bissell Brothers
Head to Bissell Brothers Brewing at Thompson’s Point for their weekly Wednesday trivia. bissellbrothers.com
- Payson Park Sled Run
Bring a sled to Payson Park and fly down the hill until your cheeks hurt from laughing.
- Curling & Brew Tour in Greater Portland
Book a tour for an intro to curling at Troubh Ice Arena followed by tastings at local breweries.mainebaycycle.com
- Igloo Dining at Alto (Canopy Hotel)
Reserve a rooftop igloo for cocktails and small plates under the stars, complete with heater, pillows, and city lights. altoportland.com
- Bayside Mural Hunt
Walk Bayside Trail and do a mural scavenger hunt, photographing all the street art you find along the way.
- Riverside Golf Course Winter Playground
Check out Riverside Golf Course’s winter layout for sledding hills, skating rinks, cross-country skiing, and snowshoe trails. riversidegolfcourseme.com/golf/winter-activities
- Heated Vinyasa in the Arts District
Try a heated class at Portland Yoga Project and then wander the Arts District for a post-class snack or tea. theportlandyogaproject.com
- Pineland Farms Snowshoeing and fat biking
Drive to Pineland Farms in New Gloucester and hit the snow-covered fields.
- Fireplace Cocktail at the Armory
Sink into a chair by the fireplace at The Armory Lounge with a classic winter cocktail or mocktail. theregency.com/dining/the-armory-lounge
- Chai + People Watching
Grab a spicy chai or seasonal latte at Tandem Coffee or Bard Coffee and people-watch from a window seat. tandemcoffee.com, bardcoffee.com
- Whoopie Pie Flight
Create a whoopie-pie taste test: start at Two Fat Cats Bakery, add Standard Baking Co., and finish with a wild-card bakery you haven’t tried yet. twofatcatsbakery.com, standardbakingco.com
- Indoor Climbing at EVO
Try climbing at EVO Rock + Fitness; rent gear if you’re brand-new. evorock.com
- Bayside Bowl Duckpin Session
Reserve a lane at Bayside Bowl, order tots, and bowl under the disco ball. baysidebowl.com
- Indoor Golf & Putting Contest
Hit an indoor golf simulator at X-Golf Portland or play mini-golf at Minibar. xgolfportland.com minibargolf.com
- Maine Celtics Game
Catch a Maine Celtics home game at the Portland Expo and share soft pretzels, high-fives, and defense chants. maine.gleague.nba.com
- State Theatre Wild Card Show
Choose a band you’ve never heard of and commit to going all in. statetheatreportland.com
- At-Home Maine Miniseries Night
Stay in, pile on blankets, and watch the HBO miniseries Olive Kitteridge, filmed and set in small-town coastal Maine.
- Mechanics’ Hall Event
Attend a lecture, concert, or literary night at historic Mechanics Hall and spend time soaking in the reading room and architecture. mechanicshallmaine.org
- Pottery Class at Portland Pottery
Take a wheel or hand-building class at Portland Pottery Studio and make yourself a winter mug or bowl. portlandpottery.com
- Give Metalsmithing a Whirl at Artascope
Learn jewelry metalsmithing basics in a relaxed workshop at Artascope Studios in Yarmouth. artascope.org
- Distillery Tour & Tasting
Tour Hardshore Distilling Company and learn the story behind a Maine winter gin or spirit. hardshoredistilling.com
- New Puzzle with a Maine Scene
Buy a Maine-illustrated puzzle from a local bookstore and keep it going all month.
- Board Game Night at Home—or Our
Plan a board game night at home or head to Another Round or Gathering Grounds for games and snacks. anotherroundmaine.com, gatheringgrounds.games
- Snow Candy Night
When it snows, pour hot maple syrup over clean snow (or shaved ice in a dish) to make maple snow candy—old-school winter magic.
- Maine Mariners Hockey Night
Cheer for the Maine Mariners at Cross Insurance Arena—pick a random player to be “your” player all season. marinersofmaine.com
- Volunteer Afternoon
Spend a few hours volunteering with Preble Street, Maine Needs, or Wayside Food Programs as a “love your city” practice. preblestreet.org, maineneeds.org, waysidemaine.org
- Harbor-View Chowder Night
Grab chowder and oysters at Eventide Oyster Co. or J’s Oyster and watch the working waterfront in winter. eventideoysterco.com, jsoyster.com
- Journals & Stacks at the Portland Public Library
Spend an afternoon at the Portland Public Library, wandering stacks, flipping through magazines, and borrowing a “February read.” portlandlibrary.com
- Winter Beach Walk at Crescent Beach or Ferry Beach
Drive out for a winter walk at Crescent Beach State Park or Ferry Beach, listening to waves crash against cold sand.