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Best Speakeasies

If you think this has been a long, cold winter, you should have been around in 1920. Prohibition had just started, making it tough to find a decent drink anywhere. Many of today’s top cocktail establishments like to affect the speakeasy vibe with passwords and secret entrances, but you can still get a glimpse of the real Boardwalk Empire at these once-illicit watering holes, where rumrunning, police raids and trap doors were just part of a regular night.

Bill’s Gay Nineties, 57 East 54th Street, New York, 212 355 0243:

While New York is alleged to have offered nearly 100,000 speakeasies at the height of Prohibition, Bill’s endures as one of the most famous and most nostalgic. The walls are a pictorial history of the dancers and desperadoes who indulged at this converted Midtown Manhattan brownstone.


What to Drink: Bronx Cocktail (gin, sweet vermouth, dry vermouth, orange juice)

Bourbon & Branch, 501 Jones Street, San Francisco, 415 346 1735:

To get into the library room at this cocktail Mecca, you’ll need a password. But the Roaring Twenties feel is not just posturing; the building was home to a basement speakeasy located below the JJ Russell Cigar Shop from 1923 to 1933, complete with five escape tunnels.

What to Drink: The Stiletto (Scotch, Averna, honey syrup, Fee Brothers Old Fashion Bitters)

John Barleycorn, 658 West Belden Avenue, Chicago, 773 348 1570:

“Barleycorn’s” ducked Prohibition by pretending to close down. The owners even opened a laundry in the rear of the Lincoln Park establishment, and the booze was smuggled in under baskets of dirty linens. Now, of course, it’s a legitimate bar and offers a cozy back room with a fireplace and a warm-weather beer garden.

What to Drink: Cocktails by the pitcher, made with locally produced 4 Rebels Vodka

The Oakroom at The Seelbach Hilton, 500 Fourth Street, Louisville, Ky., 502 585 3200:

Opened in 1905 at a cost of about $990,000, the Seelbach Hotel was a turn-of-the-century marvel. Its Oakroom served as a poker den and a pit stop for Al Capone during his exploratory jaunts to bourbon country. However, it’s the hotel’s lavish, Bavarian-inspired Rathskeller bar (pictured above), officially closed until after Repeal, where the real Prohibition imbibing occurred.

What to Drink: Seelbach Cocktail (bourbon, Cointreau, Angostura Bitters, Peychaud’s Bitters, Champagne)

Velvet Tango Room, 2095 Columbus Road, Cleveland, 216 241 8869:

While this building has housed a blacksmith, a barbershop and several legitimate bars, it retains its speakeasy character. There’s a jazz piano, a back room hidden behind a two-way mirror and a tin ceiling riddled with bullet holes.

What to Drink: French 75 (Hendrick’s Gin, simple syrup, lemon juice, Champagne)

Looking for more great watering holes? Check out our bar guide for the best bars in the world.

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