Visitor's Guide 2026

THE COZY SEASON YOUR WINTER ADVENTURE AWAITS As the temperatures drop, Greater Portland becomes a winter wonderland. With snow-dusted streets, a quieter waterfront, and the aroma of comfort food on every corner, the region invites visitors to experience its winter charm. From cozy coffee shops to world-class dining, snowshoe trails to intimate pubs, a winter day in Greater Portland promises adventure, warmth, and charm.

MORNING COFFEE + PASTRIES Start your day at one of our celebrated coffee shops. Local roasters like Coffee By Design craft every cup with care, from bold espresso to creative lattes. Pair it with hot and fresh donuts from The Eighty8 Donut Café , enjoy a hearty breakfast at Becky’s Diner with their Maine lobster benedict, or head to Another Round to sip coffee while playing a board game with friends. TRAILS + SLOPES For snow lovers, Greater Portland is a gateway to Maine’s lakes and mountains. Spend the morning at Sunday River — just under two hours away—skiing or snowboarding, then return for a cozy afternoon in the city. Closer to town, explore the historic streets of the Old Port or stroll the waterfront, where cobblestones and brick paths frame picturesque views. Adventurers can try cross-country skiing or snowshoeing along Eastern Promenade , Back Cove , and Pineland Farms . For family-friendly fun, sled at Payson Park or skate at Thompson’s Point , where open-air ice and panoramic views make winter active and magical. BREWERIES + DRINKS Portland boasts one of the most breweries per capita in the U.S. Spend your afternoon on a craft crawl through the East End, enjoy a curated tasting at favorites like Mast Landing Brewing Company in Freeport , or stop by The Great Lost Bear , one of Maine’s oldest pubs with one of the largest tap selections in the state. Prefer spirits or wine? Local distilleries and wineries serve seasonal cocktails in warm, inviting spaces. Try Cellardoor Winery Portland for a handcrafted glass of wine or Après for a delicious seltzer.

LUNCH + SEAFOOD No visit to Portland is complete without sampling Maine’s fresh seafood. Enjoy lobster rolls, chowder, or a hearty seafood platter at waterfront restaurants like Dry Dock or DiMillo’s On the Water . Winter menus highlight the season’s bounty, from root vegetables to sweet cold-water oysters, making every meal both comforting and memorable. DINNER + CULTURE Dine at award-winning restaurants like Sur Lie , featuring inventive menus and local ingredients. Then enjoy Greater Portland’s arts scene at Merrill Auditorium with Portland Ovations , the Portland Symphony Orchestra , or Friends of the Kotzschmar Organ . Sports fans can catch a Maine Mariners hockey game or a Maine Celtics basketball game. NIGHTCAP End the day by warming up by a crackling fire at local favorites like Blyth & Burrows or The Armory at the Portland Regency Hotel . For stunning views, head to Top of the East at Westin Portland Harborview , or enjoy a whimsical experience at an ice bar igloo or a rooftop lounge with snow- covered magical cityscapes. WINTER DEALS Wander the Old Port, hunt for Maine-made treasures, or explore snowy trails— Greater Portland shines in winter. Cozy cafés, intimate pubs, and scenic adventures make every day a seasonal escape. Winter Deals give you an excuse to get out and treat yourself with exclusive midweek offers from local restaurants, breweries, and lodging. Gather with friends, try something new, or plan a quick getaway. Enjoy great food, good drinks, and time well spent with deals you can find at winterweekdays.com .

Thompson’s Point

Photo by: Knack Factory

Batson River Brewing & Distilling

The Holy Donut Photo by: Emily Shawstuck Photo by: The Holy Donut

Drinking + Dining / 33