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The Ultimate Guide to North American Speakeasies

While prohibition-style cocktails – and suspenders – are in fashion again, there was a time that drinks could only consumed in secret rooms. These are those rooms.

In recent years, the allure of the speakeasy-style nightspot makes perfect sense. With the craft cocktail craze at an all-time high and bartenders donning throwback suspenders, vests and hats, it’s a scene that continues to grow.

It’s at a point now that imbibers want to absorb everything they can about cocktail culture, and that includes its darkest period. Prohibition, the ban on the production, importation, transportation and sale of alcoholic beverages, took place in parts of Canada as well as the United States. In Canada, Prohibition occurred in the late 19th century and also from 1918 to 1920. And in the United States, the ban took place from 1920 to 1933. 

But when it comes to the speakeasy title, few establishments can call themselves authentic. From bars boasting original fixtures to those with hidden passageways, we uncover some gems where patrons may indulge in a genuine experience. 

Spilt Milk

One of the more popular ways to hide speakeasies in plain sight during Prohibition was to use a pharmacy as a cover. There were many throughout the country, and one that has been recently revived after more than 20 years out of commission was this spot, located in the Logan Square neighbourhood. A few cool speakeasy tricks have been left intact, such as bells under the bar to warn customers about impending busts as well as a secret passageway for an easy escape. Spilt Milk plays up the fact that many illegal taverns sold patrons tumblers filled with milk (they also used various flavors of soft drinks) topped off with whiskey, gin or other spirits. Instead of milk, the veteran bartenders behind the stick use freshly squeezed juices like grape juice as a base for vintage cocktails. Every day guests should expect a different “cocktail of the day.”

2758 W. Fullerton Ave., Chicago, 773-413-8440 

Courtesy Spilt Milk

No crying over your Sidecar at Spilt Milk.

Beuchert's Saloon

Talk about brazen. This D.C. favorite operated right on Capitol Hill, directly under the noses of the country’s top legislators. It was under the guise of a sewing machine store, and trappings of the original storefront are still in place. The new owners, in fact, have made certain that much of the original façade from when it was built in 1880 remains in place. It’s now a farm-focused American eatery with a strong cocktail and dining program. 

623 Pennsylvania Avenue SE, Washington, D.C., 202-733-1384

Dirty Martini

Reportedly there were almost 3,000 speakeasies in D.C. during Prohibition, and The Mayflower Club was one of the city’s most prominent. Situated on the fourth floor of a building in Dupont Circle, it entertained a high-profile clientele. Its reputation eventually caught the attention of the authorities and it was raided, seizing a large stash of booze. As Dirty Martini, the venue embraces its storied history, which includes a 30-foot bar. There’s a signature dirty martini on the menu, of course, plus classic preparations of the Sazerac and other timeless tipples.

1223 Connecticut Avenue NW, Washington, D.C., 202-503-2640

Green Mill

Don’t bother asking for a tour of the tunnels rumored to be an escape path for legendary gangster Al Capone when the police – or enemies – were on his tail. The Green Mill provides live jazz and strong drinks only. Opened in 1907 as Pop Morse’s Roadhouse in Chicago’s Uptown neighbourhood, the shadowy saloon is one of the country’s oldest jazz lounges. One look around and guests can tell that much of the original fixtures have been left intact, including the well-worn booth where Capone kept court. Live music occurs seven nights a week at this after-hours institution, but don’t expect to hear anything contemporary. There’s also a Sunday night poetry slam event that’s been going on for more than 30 years. 

4802 N. Broadway, Chicago, 773-878-5552 

Hanson's Shoe Repair

Opened as a legitimate shoe repair business in the early 1880s, Hanson’s reputedly sold spirits with a shine during Prohibition. It’s located in downtown Orlando’s oldest building, which is considered a national landmark. To gain access, those who make reservations will receive a text message with a password that changes daily. The interior maintains a turn-of-the-century vibe that comes with antique shoes and old-timey photos throughout the space, which only holds 20 to 30 guests. The menu showcases classic and contemporary cocktails, which may also be enjoyed on a tiny rooftop patio. 

27 E. Pine St., Orlando, Fla., 407-476-9446

Courtesy Barber Shop

Erm, excuse me, which way to the Barber Shop?

The Barber Shop at Renaissance Blackstone Hotel

The luxurious Blackstone Hotel has played host to every U.S. president since opening in 1910. But what most people don’t know is that it was also home to a hidden barbershop that serviced the likes of JFK as well as Capone and his henchmen. So that they could enjoy some privacy, The Barbershop was tucked away in the basement, with no windows and a secret passageway to the alley for a quick getaway. Though the tiny shop wasn’t a speakeasy, its history with some of the most notorious characters makes it an intriguing venue to host special events. 

636 S. Michigan Ave., Chicago, 312-447-0955

Speakeasy Social Lounge

Another secret subterranean establishment, Speakeasy was used as storage space until it was completely restored in 2012. Back in the 1920s, there was no signage, so only those in the know knew it existed underneath the Omni William Penn Hotel. In its current state, Speakeasy is a popular weekend attraction drawing lines up the stairs and out the door. It prides itself in its vast whiskey selection, which includes four vintage bottles of rye from the early 1900s.

530 William Penn Place, Pittsburgh, 412-281-7100

Stanza Dei Sigari

Located in Boston’s oldest residential neighbourhood of North End, Stanza Dei Sigari is on the lower level of Caffè Vittoria. The upscale cigar lounge is known to attract heavy hitters (Rob Lowe was seen puffing here a few times when he was in town filming a new movie) and local politicians for its expensive stogies and single-malt scotches. Little is known about the history of the 1920s-era tavern shrouded in mystery, but leftover relics from that period include a gated cigar vault, low-slung ceilings and a smattering of vintage photos of notables puffing their favorite brands. 

292 Hanover Street, Boston, 617-227-0295

Museum of the American Gangster/Theater 80 St. Marks Place

Lorcan Otway is proud of the fact that he was born in a former speakeasy. And he’s taken that legacy one step further by transforming his birthplace into a legitimate moneymaking business. Downstairs from the speakeasy, which is now the theater, is the Museum of the American Gangster, where Otway’s carefully curated all sorts of historic documents and memorabilia. The two-room institution is especially ripe with cool things from the Prohibition era, from seven .45-caliber bullets from the St. Valentine’s Day Massacre to original sheet music from songs of the time like “It’s the Smart Little Feller Who Stocked Up His Cellar That’s Getting the Beautiful Girls.” You cannot grab a drink in the museum, but the theater, which showcases open-run performances such as Beverly Hills 90210 The Musical!, features a full-service bar. 

80 St. Marks Place, New York, 212-228-5736


Published Wednesday, December 7th 2016

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