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The 12 best speakeasy bars in Boston

Secret doors and underground hideaways present the perfect place to sip craft cocktails

Edited by
Olivia Vanni
&
Jillian Dara
Contributor
Linda Laban
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Some of Boston’s oldest bars may have once operated as legitimate speakeasies during the Prohibition era, but nowadays, our city’s most discreet spots serve legal drinks while replicating that nostalgically secretive atmosphere of the 1920s. Often dimly lit and under-marketed, these establishments aren’t just “bars” you happen to stumble upon. These suave parlours, basements, nooks and crannies have a focus on inventive craft cocktails and welcome clientele who are in-the-know. Start at one of these speakeasy-style bars and then add some entertainment at one of Boston’s best karaoke bars, best trivia nights or best comedy clubs.

RECOMMENDED: See the full list of the best bars in Boston

Best speakeasies in Boston

  • Bars
  • Cocktail bars
  • Beacon Hill
  • price 2 of 4

By the name alone, you can tell this 1920s-inspired bar is going to have a little fun, at the expense of our country's temperance movement and Prohibition history. If Carrie Nations main bar is too full or brightly lit, head past the shoeshine stand and up the back stairs to its secret speakeasy. Here, the Beacon Hill establishment offers pool tables and intimate seating. No matter which corner you choose to imbibe, you can select from a menu of both modern and old timey cocktails, ranging from punches and barrel-aged libations to well-crafted classics. 

  • Restaurants
  • Cuban
  • Downtown
  • price 3 of 4

This downtown hotspot is both a restaurant and a lounge dedicated to pre-revolutionary Havana. While the front-of-house restaurant and rum-lined bar sets the mood with a first impression, it’s the unmissable downstairs (aka Mariel Underground) that truly emphasizes Mariel’s tribute to a different moment in island time. Not always easy to get into, it’s worth the wait. Try your hand by ordering a daiquiri—only the real deal here, sans frozen berries—at the front bar and waiting patiently for first-call of the evening.

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  • Bars
  • Leather District

Sandwiched between FiDi and Chinatown in Boston’s gradually evolving Leather District, Offsuit is an unassuming bar tucked inside Troquet on South’s French bistro. A backdoor entrance ensures a distinctly intimate experience, where burgundy walls, leather love seats and spinning vinyl impart a brooding aura you'd expect from a Prohibition-era speakeasy. Order from a list of classics or trust the bartender's choice at this tiny, 20-seat spot; the beverage directors craft up original recipes seasonally.

  • Restaurants
  • Bakeries
  • North End
  • price 1 of 4

Modern Pastry is an iconic North End pastry emporium with a loyal following. This family-owned spot has been in operation for decades, offering old-world cakes, cookies, pizelles, and chocolates. Lesser known is the sweet cocktail spot downstairs. Check out Modern Underground where you can get a well-made cocktail with your dessert.

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  • Bars
  • Cocktail bars
  • Somerville
  • price 2 of 4

This relaxed drinking place has the ad hoc feel of being off the beaten track. The entrance isn’t easy to find at first; it is down an alley, after all. The attention to detailed drinking is what pulls patrons in. Lean in over the bar and impart your fancy — the barkeep will do their best to meet that in a cocktail. Classics? No problem. Star Wars? It’s a thing: try the Millennial Falcon (mezcal, sweet sherry, amaro) or the Bananakin Skywalker (Scotch, pineapple, banana).

  • Bars
  • Cocktail bars
  • price 2 of 4

Baldwin Bar in Woburn has become a destination for connoisseurs to enjoy expertly-made classic cocktails. Look a little harder and you'll find the bar-within-a bar, Baldwin & Sons Trading Company. This cozy lounge focuses more on kitsch, with tiki glassware and exotic ingredients like acidified papaya pandan compound.

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  • Bars
  • Cocktail bars
  • Roxbury
  • price 2 of 4

What better place to sample booze than right where it’s made? From whiskey and rum, to gin and amaro, this local, family-owned distillery is certainly off the beaten bar track; located in Boston’s industrial Newmarket area. Guests can visit for a distillery tour and tasting, or they can simply pop-in for a cocktail made with the brand's original spirits. The 26-seat tasting room has a Prohibition-era speakeasy vibe, with vintage fittings and a long black marble bar overlooking the stillroom.

  • Bars
  • Central Sq
  • price 2 of 4

Head through Roxy's Grilled Cheese to the freezer door in the back and step into a hidden world of throwback fun for adults. The forces behind Area Four operate this speakeasy arcade filled with ‘80s classics (Galaga, Ms. Pacman). The distinctly grownup cocktail menu impresses, as does the selection of local craft brews.

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  • Bars
  • Cocktail bars
  • Central Sq
  • price 2 of 4

Find this hidden Central Square gem by heading through a nondescript door and up a set of stairs. A giant horseshoe-shaped bar and ample stool seating make for a hip environment to enjoy expert mixology. The cocktails shine and the bar snacks (which include deviled eggs and “grandma’s” gooey garlic bread) are done just right.

  • Bars
  • Cocktail bars
  • South Boston
  • price 2 of 4

GrandTen Distillery has its own bar that’s open only Fridays through Sundays. Walk through a garage door and into the little known watering hole, where its cocktail menu is written on a chalkboard-painted concrete column. Drink offerings are creative (thanks in part to our local draconian liquor laws that only allow them to use spirits distilled onsite), while shuffleboard, foosball and throwback board games invite you to make a full night of it.

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  • Restaurants
  • Contemporary American
  • Downtown
  • price 3 of 4

At the heart of the Downtown Crossing, you can descend a dark stairwell for access to Boston’s spritely-designed supper club. The sitting room just off the bar is doused in animal-print and rich mahogany wood—a refined coexistence of feminine and masculine decor. This sexy, yet strong energy reverberates from the cowhide chairs and candle-lit tables, to the library-styled walls and flaming cocktails served from the protruding marble bar.

  • Bars
  • Cocktail bars
  • Seaport District
  • price 3 of 4

When Drink first opened in 2008, the concept of a menu-less cocktail bar attracted the masses. Today, the sunken lounge located below Chef Barbara Lynch’s Sportello still beckons savvy spirits enthusiasts with its underground appeal to sip on something “different.” Whether you’re in the mood for something tequila-based and spicy, sweet and topped with champagne, or a total surprise, Drink’s mixologists are sure to deliver.

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