Revisiting the Past: Historic Detroit Speakeasies

Modified: September 30, 2020 | Story by Biba Adams | Photos by Image courtesy of Nancy Whiskey

Women dressed in flapper clothing, the Harlem Renaissance, American Gangsters-these are the romanticized images of the “Roaring 20s.” In actuality, the decade was one of an unregulated stock market that created a rich, ruling class, and triggered the Great Depression.

The 20s was also the decade of prohibition. From January 1920 to December 1933, there was a national ban on the production, importation, transportation, and sale of alcohol.

The law lasted 13 years, but the effects would be a part of America forever. Prohibition was a bad law with good intentions. There was never any proof that the law reduced crime or health problems. Instead, it was prohibition that directly lead to the rise of organized crime in America.

The “mafia” as we know it now, benefited from breaking every single aspect of the laws that supported prohibition. Characters like Al Capone and Lucky Luciano remain shadowy parts of American history.

Detroit played a huge role in bootlegging during prohibition because of the close proximity to Canada. The Purple Gang, a group of Jewish bootleggers, supplied the Midwest with whiskey they snuck over the border. Historians even claim that at the bottom of the Detroit River, there are still cars from The Purple Gang filled with barrels of whiskey.

Prohibition also brought about the “speakeasy,”- secret bars where people drank illegal alcohol during the ban. Often disguised and hard to enter, speakeasies had a secret society feel to them. In Detroit, 100 years later, there remain several bars that were speakeasies back in the 20s. And if their walls could talk, what tales they would tell.

Detroit Speakeasies

Two Way Inn

Two Way Inn is the oldest bar in Detroit. According to them, they have been selling spirits since 1876 without stopping. Confirmed as a speakeasy during Prohibition by the Detroit Historical Society, the Two Way Inn sold legal and illegal alcohol in the 1920s by filling prescriptions from a doctor and dentist, as well as selling bootlegged alcohol. “Speakeasies were well-protected and very hush-hush,” says Danielle Aganowski, daughter of the owner, “People wouldn’t talk too much about it for fear of ruining a good thing.”

The history and legacy of the bar is sacred to the owners. Since 1973, the Two Way Inn has been owned and operated by one family. The owner, Mary Malak Aganowski inherited the bar from her father who bought it in his youth. “We have stayed in Detroit and in this neighborhood through thick and thin,” says Danielle, “We want only positive things for this city.”

These days, Two Way Inn is known as an old school “shot and a beer bar,” with great prices and beer selection. Every Sunday, stop by for Mary’s signature “Bloody Sunday” brunch.


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Nancy Whiskey Pub

Established in 1902, Nancy Whiskey Pub is one of the oldest bars in Detroit. Steeped in the rich Irish tradition that founded Corktown, Nancy Whiskey still serves up a free shot of Tullamore Dew to anyone who is in the bar for their very first time. At Nancy Whiskey, there is only one kind of beer on tap, Guinness.

During Prohibition, Nancy Whiskey was a secret speakeasy, with a stairwell that hid liquor. Yet, their gangster history didn’t end there. The pub was known as one of Jimmy Hoffa’s regular hangouts. In fact, he was known to sit in the telephone booth at the pub and conduct business.

Having survived a devastating fire in 2009, Nancy Whiskey Pub still has its Irish flair and dedication to history and legacy. A great place to watch the St. Patrick’s Day parade, any Friday of the week is also a perfect day to stop by for a traditional Irish fish fry.


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Tommy’s Detroit Bar

In 2012, an archaeological dig by Wayne State University uncovered hard evidence of a Purple Gang gambling room in the basement of the building that houses Tommy’s. The explorers also discovered the collapsed remains of a tunnel that allowed patrons and bootleggers alike to sneak in and out of the building.

In addition to its colorful gangster past, this building is speculated to have also been a stop on the Underground Railroad before escaped enslaved African Americans were spirited away to Canada. Given its rich history, it’s no wonder that Tommy’s is also considered a hotbed of paranormal activity. It’s haunted, perhaps, by the ghosts of the gangsters who once gambled there or enslaved people seeking freedom.

These days, Tommy’s Detroit Bar is a great place to stop by just to soak up the history. The bar offers regular tours of its iconic basement, and while you’re there you can indulge in their fresh, never frozen burgers and wings. Tommy’s Detroit Bar also offers shuttle service to the District Detroit so that patrons can head off to Lions, Tigers, or Pistons games.

Detroit has a rich Prohibition history. It is regularly celebrated by the Detroit Historical Museum as well as Detroit Prohibition Tours led by the Detroit Bus Co. But book early, these tours fill up fast.


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Mentioned Attractions And Venues

  1. 1
    Nancy Whiskey
    2644 Harrison St., Detroit, MI 48216
  2. 2
    Two Way Inn
    17897 Mt Elliott St, Hamtramck, MI 48212, USA
  3. 3
    Tommy's Detroit Bar
    624 3rd Ave, Detroit, MI 48226, USA