11 Cozy Bars and Restaurants in Portland, Maine Perfect for Winter

A true, unpretentious watering hole, Rosie’s is one of the few places in Portland where the only difference between patrons is whether they’re getting the wings or fried chicken tenders. Compact and softly lit, Rosie’s is a friendly neighborhood bar, in business now for more than 30 years. Maybe it’s the brick, the wooden tables, the games or the simple fare, but you can walk into Rosie’s and feel like you’ve stepped back to a time when the bartender knew your name, and your order.

Sure, Local 188 is one giant open dining room and kitchen. Maybe it’s the lofty ceilings, the low, soft lights, the couches or the nooks and odd crannies, but few restaurants in Portland conjure low-light magic as well as this place does. Each section—whether the counter or the dining room or the bar and its leather couches—is oversized and yet feels separate. Especially on winter nights, the stools around the bar overlooking Congress feel proprietary. The renowned local farm food and original cocktails aren’t bad either.

Without a doubt, the food at Five Fifty-Five is a gourmand’s dream—an upscale dining experience tucked inside a casual bistro. But the intimate tables, the low murmur of other patrons plugged into their meals and each other, the flickering candles and soft accents make it one of Portland’s coolest and coziest restaurants.

Munjoy Hill has transformed from a no-go locale to a must-go, hip neighborhood of small boutique restaurants, such as Lolita, where the interior is as intimate as the meals. Maybe it’s the filament lights hanging over the bar. Perhaps it’s the tables where dates and old friends sit rapt over carefully laid-out meals or the bottles of wine in bookshelves over the tables or—you get the idea. The chef handpicks the meat and cheese on the customizable plates, and the hot plates feature small bites of Maine seafood and shellfish.

Friends meeting up in the city, first dates, 50th anniversaries—the cozy North Point is perfect for any occasion. Compact yet comfortable, it has some of the best cocktails in Portland without the prices of pretentious places. The plush cushions along the windows invite long chats over candles, or the breadth of the appetizers will keep you going as the conversations enter the second, then third, hour.

Hugo’s hits the three F’s—foraged, fished and farmed—which are almost a requisite for being a popular Portland bistro these days. But the James Beard winner is about so much more than the food: dining here takes on a relaxed atmosphere as the deep, blush booths next to the open kitchen allow patrons to watch the chefs studiously practice their craft. The place feels dusky, almost timeless, and the amble wines and heady cocktails ensure that you don’t have to go until you want to.

An underground speakeasy risks feeling more like a dungeon than a private enclave if not pulled off right. Luckily, Bramhall gets in on the cozy side, with its arched brick walls, recessed bars, moody lighting and unpretentious—but the city’s best—drinks. In fact, the only danger at Bramhall is getting so comfortable that you lose track of time, lulled by drinks and shrine-sized candles.

There’s one word to describe Petite Jacqueline, and it’s snug. This warm, friendly French bistro is open and sunlit by day, transforming into a meditative space perfect for solo diners, dates, and everything in between by night. It offers serious food without the solemnity, and the windows drape patrons in light overlooking a handsome Portland square.

Perched atop Munjoy Hill in a compact, but never uncomfortable double room, the Blue Spoon fits just a few patrons, making it a perfect option for a date or quiet night out. The hardy dishes feature Maine fare, and the burger is one of the best in town. Coupled with the warm waitstaff and agreeable prices, and it’s hard not to feel at ease—and at home—here.

The Front Room put Munjoy Hill on the map as an up-and-comer. It is a street-level, wide-open restaurant with oversized wood furniture, a stone fireplace and portion sizes that guarantee you’re going to get cozy. The brunch is the stuff of lazy Sunday heaven, while the streetside windows overlook a quiet part of historic Congress Street and the Eastern Promenade.

Come for the food and drinks, and stay to soak up everything else. The restaurant has an open kitchen where award-winning chefs create culinary magic; dim lighting; beautiful people pouring over paper menus; and a bar, with no shortage of brass, mason jars, and boutique booze. Central Provisions provides a respite, a cozy retreat from the Old Port knocking outside.