From refined bars to light-up dance floors, these recommendations will ensure that whatever happens on the date, at least the setting will be memorable.
DRIFTERS WIFE | 63 WASHINGTON AVE.
The owners of Maine and Loire wine shop started pouring out natural wines at this bar-within- a-shop earlier this year. The bar, like the menu, is small, but it makes for a cozy, intimate date. The decor is pared down, letting you focus on your date (or just the wine).
DUCKFAT | 43 MIDDLE ST.
This casual eatery does everything well and serves as a perfect first date, as Emily McConnell, special projects, found. “Sergio and I had our first date over milkshakes at Duckfat. Love at first slurp,” she says. “We try to go there every year on our anniversary.”
THE ARMORY LOUNGE | 20 MILK ST.
The bar in the lower level of the Portland Regency Hotel and Spa is refined without being stuffy. With low lighting and comfortable armchairs, it’s a fine way to avoid the bustle of the Old Port, especially if you don’t want to be bothered (or seen).
MACWORTH ISLAND | ANDREWS AVENUE, FALMOUTH
Although it’s not in Portland, Mackworth Island is close and accessible enough for an outing that won’t take up your whole day. The 1.25-mile trail that loops around the island is a serene walk through nature any time of year.
ARCADIA NATIONAL BAR | 24 PREBLE ST.
This bar has a small but well- curated tap list and video game–themed cocktails. But the games—classic arcade and pinball machines and stacks of board games—are the real draw for couples with a competitive streak.
BAR AT FORE STREET | 288 FORE ST.
Fore Street is a culinary destination, but its bar area makes an ideal date setting. Candles and soft lighting highlight the laidback, rustic elegance of the place, and unlike most of the seats in the restaurant, you don’t need reservations at the bar.
RUSKI’S TAVERN | 212 DANFORTH ST.
This West End brunching and drinking institution can serve as a test balloon for potential pairs. “Being comfortable in this divey but cozy bar is true testament to a relationship’s longevity,” says advertising account manager Jessica Goodwin. “If they can’t hang here, nip it in the bud.”
PAI MEN MIYAKE | 188 STATE ST.
During warmer months, the outdoor communal table in the middle of Longfellow Square is fun, but on cold nights it’s tough to beat sitting across from someone special with
a warm, comforting bowl of ramen.
SATURDAY FARMERS’ MARKET | DEERING OAKS PARK
The weekly market provides a good excuse to take a stroll through Deering Oaks Park. Editor-in- chief Susan Grisanti recommends extending the date by grabbing some fresh produce and heading back home to cook.
LOLITA VINOTECA + ASADOR | 90 CONGRESS ST.
A Munjoy Hill favorite, Lolita has a warm and welcoming atmosphere, an extensive, thoughtful wine list, and small plates that encourage you and your date to experiment. The patio opening up in the summer months is a bonus.
MAPS | 64 MARKET ST.
This below-street-level bar provides all you need for a date: spinning vinyl, cozy seating, beer, wine, and cake. Multiple cakes. Because sometimes it’s better not to settle on just one.
BUBBA’S SULKY LOUNGE | 92 PORTLAND ST.
Fridays are ‘80s night, with a light-up dance floor and one of Portland’s best disc jockeys, DJ Jon. Dressing up lets you avoid the cover charge and gauge a date’s adventurousness (and stock of neon leggings and Members Only jackets).