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Wink & Nod
Photograph: Courtesy Wink & Nod/Atsushi Tomioka Wink & Nod

The best Boston speakeasies

Prohibition is long over, but the alluring idea of the hidden speakeasy lives on

By Linda Laban and Time Out Boston Staff

While they are no longer the illegal drinking parlors set up behind false walls to evade authorities during Prohibition, the allure of the speakeasy is still strong. Some of Boston’s oldest bars undoubtedly operated illegally as speakeasies during the Prohibition era, but many new establishments replicate the atmosphere, discreetly tucked away in the back of a restaurant or down an alley. They are cool and low-key, where a well-made cocktail is the focus. Start at a speakeasy-style bar 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

Lucky's Lounge
Photograph: Michael Ascanio Peguero

1. Lucky’s Lounge

Bars Lounges Seaport District

Lucky’s is so discreet as to be almost hidden: With naught but a sandwich board marking the entrance down a few steps, you’d be forgiven for passing by this longstanding lounge in Fort Point. The cocktails are well made; the food too good for Lucky’s to be considered a dive bar. It’s simply a classic that harks to mid-20th Century lounges and pays homage to Frank Sinatra’s rat pack with portraits of ol’ blue eyes and a swinging Sinatra Sunday Brunch. 

Photograph: Zac Wolf

2. A4cade

Bars Central Sq

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.

Wink & Nod
Photograph: Courtesy Wink & Nod/Atsushi Tomioka

3. Wink & Nod

Bars Cocktail bars South End

Though a modern addition to Appleton Street, this subterranean bar is furnished as an old school drinking den, albeit one with top-notch spirits and classy fittings such as the elaborate pressed tin ceiling. It’s doubtful any furtive speakeasy looked this good; immersed in a bygone style, the softly lit, sunken level bar serves up exquisitely created drinks with house-made cordials, syrups, and accouterments. Go for broke with the ever-changing, rather expensive Black Card Cocktail, which might set you back $100.

Brick & Mortar
Photograph: Michael Ascanio Peguero

4. Brick & Mortar

Bars Cocktail bars Central Sq

Find this hidden gem next to Central Kitchen by heading through the nondescript door and up the stairs. A giant horseshoe-shaped bar and ample bar stool seating make for a hip environment to enjoy expert mixology. The cocktails shine and the bar snacks (which include bacon-wrapped dates and deep fried house made pickles) are done just right. 

Photograph: Michael Ascanio Peguero

5. Backbar

Bars Cocktail bars Somerville

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).

The Baldwin Bar
Photograph: Courtesy Baldwin Bar

6. Baldwin & Sons Trading Company

Bars Cocktail bars

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.

Modern Pastry
Photograph: Courtesy Yelp/Alice S.

7. Modern Pastry

Restaurants Bakeries North End

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.

GrandTen Distilling
Photograph: Courtesy Yelp/Mary Kate A.

8. GrandTen Distilling

Bars Cocktail bars South Boston

GrandTen Distillery has a bar that’s open Thursdays through Sundays. Walk through a garage door into the in-the-know space, where the creative cocktail menu—creative in part because our draconian liquor laws only allow usage of spirits distilled onsite—is written on a chalkboard-painted concrete column. Shuffleboard, foosball, and throwback board games invite you to make a night of it.

Photograph: Courtesy Yelp/WINE A.

9. Capo Restaurant

Restaurants Italian South Boston

Capo serves up Old World pleasures with pizzas, homemade pastas, and classic entrees like eggplant parmesan and chicken cacciatore. Downstairs, the Supper Club deals in 1920s-era style with dinner-and-a-show six days a week. Live music, Sinatra faves, and standup fill the roster. Well-made cocktails round out the experience.

Bully Boy Distillers
Photograph: Courtesy Bully Boy Distillers

10. Bully Boy Tasting Room

Bars Cocktail bars Roxbury

What better place to sample the booze than where it’s made? This local, family-owned distillery is certainly off the beaten bar track; it’s located in Boston’s industrial Newmarket district, between Back Bay and Dorchester. The 26-seat tasting room has a Prohibition-era speakeasy vibe via vintage fittings and a cozy, retro flair, anchored by the long black marble cocktail bar. The house spirits are made into all sorts of elegant cocktails, or can be sipped solo. A picture window in front of the bar gives a direct view of the copper still where the spirits are brewed, and there’s no bathtub in sight.

Photograph: Courtesy Yelp/Kimberley H.

11. Explorateur

Restaurants Downtown

Tucked off the open plan Explorateur café-bar-eatery, the Library Room is a discreet spot to relax. Built in 1898 as the historic Grand Masonic Lodge was wholly a private place, and the Library Room gives a view of that secretive, private club nature. It’s open everyday to all, unless there is a private event. It feels more grown-up that the main room; more moody, with lower lights, and old carved heavy wood accents, more of a nighttime kind of space. Most patrons aim for a seat in the bustling main room, but lounge lizards head here to nurse, say, a Corpse Reviver or two.


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