Courtesy Flickr user Matte.
Illicit rum running, clandestine basement meetings and stealthy attempts to evade authorities. During Prohibition, all of these were common occurrences, especially in a city like Milwaukee that enjoyed imbibing. Now that alcohol is legal, many people are still fascinated by this time period of American history. Whether an establishment was actually operating during Prohibition or was opened more recently as a themed bar, speakeasies offer patrons a glimpse of what a tavern was like during the noble experiment.
Bugsy’s Back Alley Speakeasy
Like many of the original speakeasies, Bugsy’s has a “front” business—in this case, Gouda’s Italian Deli. (Unlike most front businesses, Gouda’s is actually legitimate.) True to its name, you enter Bugsy’s from an alley, so unless you know what you’re looking for, you will miss it. Once you get through the bank vault-like door, you’ll be greeted with live music, dancers in skimpy flapper garb and a Roaring Twenties vibe. The drink menu is filled with old-school classics, just as you’d expect: sazaracs, French 75s, sidecars and old fashioneds. Beer, wine and modern cocktails, are also available; try The Devil’s Daughter made with tequila and muddled jalapeños topped with champagne. Unlike historical speakeasies, this one’s got a great happy hour and drink specials.
The Safehouse
The Safehouse is Milwaukee’s most well-known speakeasy, developed with a spy theme. Though it was recently acquired by the Marcus Corp., it’s still full of quirky passageways, kitschy décor, secret passageways and those CCTVs showing the entrance. The menu has been overhauled and streamlined, including the cocktails, many of which still come in a souvenir glass. There’s a mission—if you choose to accept it—that works as an impetus to explore the space, and maybe even find the secret exit. While this is a big tourist destination, every Milwaukeean should make a point of experiencing this classic spot at least once. Just don’t tell anyone the password.
Bryant’s Cocktail Lounge
Though Bryant’s opened in 1938, five years after Prohibition ended, it’s got arguably the best speakeasy lounge atmosphere in the city. Christmas lights and a fish tank behind the bar provide much of the light in the lounge downstairs and, coupled with cozy booths, make it feel pleasantly cave-like. Upstairs in the Velvet Lounge, the swankiness continues, with retro vinyl chairs and velvet wallpaper. There is no drink menu here; the amount of drinks the bartenders can make is so vast that it would be unwieldy. Instead, tell the bartender what kind of flavors or liquors you like, and they’ll concoct something fantastic right on the spot. A number of drinks were invented here as well, like the Pink Squirrel and Blue Tail Fly, both popular at Wisconsin supper clubs.
Shaker’s Cigar Bar
I imagine it’s not unusual for speakeasies to be haunted, given the clandestine activities that took place inside. Shaker’s is no exception, and bills itself as the most haunted bar in Milwaukee. Though the bar only dates to the 1980s, the building was constructed in 1894 and has a storied history of documented deaths on the premises. It also served as a speakeasy, and under the guise of a soda bottling line, imported alcohol from Canada. It’s been used as a movie set and featured on TV for its spiritual—liquor and otherworldly—history. But don’t be scared, as long as you stay in the bar to have a few Manhattans, a cigar or some of their Cajun-inspired food, the spirits should leave you alone. All bets are off during the tours in other pars of the building, though.
Swingin’ Door Exchange
Though it’s changed hands a few times over the years, Swingin’ Door was originally opened in 1933 to celebrate the end of Prohibition. Housed in the 1879 Mackie building, it was called the Grain Exchange Tavern back then. Considering the tavern probably existed before its official opening the very month Prohibition was repealed, chances are it may have been a speakeasy. There are old photographs on the wall of the bar, including one of the tavern’s grand opening, giving you something more interesting to gaze at than the TV. Practically every surface is covered in dark wood paneling, except for the stained glass windows. The huge one at the entrance casts a deep red glow over the main bar area. The vibe of the bar is that of a regular workingman’s tavern and drink specials like cheap cans of PBR reflect that. The food that comes out of the kitchen is top notch though, so plan to dine on fish fry or barbecue ribs.
Sidebar: Adventures in Drink at Twisted Path
Part of the experience of visiting Twisted Path Distillery’s tasting room is the adventure of just getting there. Located inside the bustling Lincoln Warehouse, the name of the tasting room—Dock 18 Cocktail Lab—gives you a clue on how to get inside. There are only 17 loading docks, so go where number 18 would be and press the button to get buzzed in. Once you’re successfully inside, no ’20s attire is necessary, as this is a thoroughly sleek, modern bar. Because it’s a distillery tasting room, it’s only legally allowed to serve its own spirits, but that is the impetus that drives their never-ending experimentation. The cocktail menu changes weekly, based on what house-made concoctions, infusions, tinctures and syrups are available. You can just show up to the tiny bar, but make a reservation for a 90-plus-minute cocktail tasting to really feel like a VIP.
