Sneak into the Five Best Speakeasies in Boston

By Eric Twardzik
02/09/2022
Best Speakeasies in Boston
backbar

The Prohibition-era days when cocktail bars had to operate in secret are blissfully behind us. However, modern underground bars abound because entering a speakeasy is just plain fun—as long as the drinks are good. For the right vibes and coolest craft cocktails, follow us to the five best speakeasy-style bars in Boston.

Yvonne's

Best Speakeasies in Boston

Yvonne’s isn’t exactly hidden—its presence in Downtown Crossing is announced by a neon-lit sign—but the entrance is still something of a head-fake. Would-be revelers encounter what appears to be a disused beauty salon, before a host leads the way to reveal a sprawling supper club. The hidden gem features two bars and Gilded Age details aplenty: the molded ceilings and carved wooden bar—circa 1886—are preserved from its tony previous tenant, Locke-Ober. The cocktail menu features old-school standards like the Ward 8, a rye-based sipper that was invented at Locke-Ober; along with house creations, large-format cocktails, and one of the best Espresso Martinis in Boston.

Stanza dei Sigari

Stanza dei Sigari

Unlike the modern underground bars on this list, Stanza dei Sigari was first a speakeasy out of necessity: North End residents gathered here to imbibe on the sly during Prohibition. Now it’s Boston’s last remaining cigar bar, but Stanza attracts even non-smokers to a historic subterranean space that’s only accessible via a steep staircase. For an unmatched authentic experience in Boston, take a seat at the molded wooden bar or in one of many leather armchairs to enjoy craft cocktails, such as an extra-boozy Espresso Martini or the M&M, a Manhattan variant made with a rosemary-vanilla-cinnamon simple syrup.

Offsuit Boston
Credit: Nick Brisbois

Discreetly located at the back of sister restaurant Troquet on South, Offsuit keeps a low profile by being accessible only via a barely marked service door on a narrow side street in Boston’s Leather District. Finding the intimate cocktail lounge is worth it for refreshingly unpretentious drinks, made with hand-carved ice. It’s the kind of place where the lighting is low and albums are played from end-to-end on a turntable. Offsuit makes a handful of reservations available early in the evening; otherwise, be prepared to put your name down and wait.

Interior of the Tasting Room at Bully Boy Distillers
  • Cocktail Bar · $$

Among industrial buildings and through a couple of mysteriously marked doors, cocktail fans will find Bully Boy’s Roxbury distillery and a tiny tasting room. The latter could pass for a Mad Men-era cocktail lounge—until you glimpse the working stills from behind the bar’s windows. The chic, dimly lit tasting room serves up freshly made spirits by the flight and in cocktails both classic and original. Here’s another secret you’ll want to be in on: Ask the bartender about the rotating draft cocktail options and the oft-changing barrel-aged cocktail. 

backbar

Backbar Best Speakeasies in Boston

Down a nondescript hallway in a nondescript building, the entry into Backbar is an ironic introduction for a cocktail bar buzzing with creativity. The inventive drinks at this hidden gem are top-notch, but Backbar never takes itself too seriously. Just look at the always-changing themed cocktail menus that riff on everything from Lord of the Rings to world maps, bears, and even Encanto. Another thing that makes this underground bar so special? Union Square neighbors Field & Vine and Littleburg provide a food menu of snacks with seasonal ingredients.

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