Some of Milwaukee's secret saloons remain a mystery, while others are well-known and beloved in the community.

Pedestrians foot past us en route to a film at the Oriental Theatre. We take a quick peek inside Sip & Purr cat café, then make a sharp turn into Black Cat Alley, just off Kenilworth near Prospect. Where in the world are we going? We’re not even sure, except there’s got to be a door.

In about 100 feet, we spot a chain-link fence with an opening to another short walkway. This looks promising. In another 10 paces, we press the buzzer outside another door, which upon entry leads to a tiny, very dark, otherworldly bar, its Cream City brick walls dotted here and there with old movie posters. We’ve accessed Shanghai, the “speakeasy.” And nobody’s here. Maybe Shanghai is a little too mysterious …

We love enigmatic destinations, whether it’s the challenge of finding them or their often time-traveling nature. The best-known local example of such a venue is the 53-year-old, espionage-themed SafeHouse, located off an alley near Wells Street.

The retro rec room ambiance at Naughty Angel, inside Don’s Diner. Photo courtesy of Chris Kessler.

This reclusive theme has come around again with more gusto just in the past several years. It might come as a surprise that Bugsy’s Back Alley Speakeasy has been offering a 1920s-era spirit – complete with dancers dressed as flappers – for six years. There are two ways to find this Third Ward hermit: through a clandestine entrance inside Gouda’s Italian Deli on Water Street, or a vaultlike door in the dark alley behind it. The interior is similarly murky, the drinks (sidecar, old fashioned) fairly unremarkable. But you may just get swept up in the mood and music, including live performers after 9 p.m. (218 N. Water St.; Thurs-Fri from 5 p.m., Sat from 7 p.m.)

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Bugsy’s and Shanghai are speakeasys only in the sense of their hidden locations, though it’s fun to think of the “illicit” side of the Depression-era establishments. That’s part of the charm. Shanghai’s vibe, using a movie analogy, is The Pink Panther meets Casablanca. It’s little more than a few dimly lit tables and a very small bar where the bartender doles out stout refreshments like the bracing, gin-based To Catch a Humming Pig. (2238 N. Farwell Ave.; Wed-Sat from 6 p.m.)

Bugsy’s hideaway conjures up the Prohibition era. Photo courtesy of Bugsy’s.

Not a speakeasy but rather a cavelike rec room of the dining room of Don’s Diner, Naughty Angel is a time warp back to the ’70s. Vinyl bar chairs frame the square bar that eats up the room, given the full Watergate-era treatment of red plush carpeting, wood-paneled walls and patterned wallpaper. Dig into the scrumptious, drippy-juicy Naughty burger and the Crock- Pot old fashioned, which is really served in a slow cooker. You’ll want to consider an Uber for this field trip. (1100 S. First St.; Fri-Sat from 5 p.m.)

Perhaps as you read this, you’ll be able to penetrate the confines of The Dark Room (“TDR”), the super-secret steakhouse at the new Saint Kate art hotel. Clues have been so scarce that even the gabby server at the hotel’s lobby bar wouldn’t spill any beans to me. I do know that like most any mystery that involves food and drink, I will get to the bottom of it.


“Secret Saloons” appears in the September 2019 issue of Milwaukee Magazine.

Find it on newsstands beginning September 2, or buy a copy online.

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