From hidden stills deep in the Appalachian hills to smuggling rings operating under city streets, Prohibition (1920–1933) sparked a rebellion that made bootleggers and moonshiners American legends. When the federal government outlawed alcohol, it didn’t stop people from drinking. Instead, it simply drove the liquor trade underground. Cities across the U.S. became centers for illegal distilling, smuggling, and secret speakeasies, fueling a thriving black market and turning everyday citizens into outlaws.
Moonshine in the Hills: Appalachian Bootleggers
Long before Prohibition, families in the Appalachian region of Ohio, Kentucky, and West Virginia had been distilling homemade whiskey, known as moonshine. The mountainous terrain made it easy to hide illegal stills while winding backroads provided escape routes from revenue agents, or “Revenuers.” Bootleggers used fast cars modified for speed and handling to outrun the law, a practice that later inspired the birth of stock car racing and NASCAR. Springfield, OH, played a key role in this network, with moonshine runners making their way from rural distilleries to urban customers.
Smuggling Hubs: Detroit and Cleveland
Prohibition created a booming smuggling trade, and no city benefited more than Detroit, MI, with its proximity to Canada, where alcohol remained legal. Detroit became the main entry point for smuggled whiskey, rum, and gin. Bootleggers used speedboats to cross the Detroit River, bringing in massive quantities of liquor under the cover of night. Some even built secret tunnels to move alcohol undetected.
Further east, Cleveland, OH had its own smuggling network, using Lake Erie as a transportation route. Boats from Canada would drop off shipments near Cleveland’s shores, where the goods were quickly hidden and distributed. The city’s underground liquor trade was so extensive that even law enforcement officers were sometimes in on the operation.
Big-City Speakeasies
While rural areas supplied the liquor, major cities provided a market for speakeasies with hidden bars that operated behind secret doors and unmarked entrances.
- Cincinnati, OH, just outside of Springfield, Ohio, had a deep underground network, with illegal bars flourishing in basements, backrooms, and hidden tunnels. Bootleggers often bribed police to look the other way, making it easier to keep the drinks flowing.
- Chicago, IL, became infamous as the home of Al Capone, the most powerful bootlegger of the era. Capone’s empire controlled breweries, smuggling operations, and speakeasies, making him one of the wealthiest and most feared figures of Prohibition.
- St. Paul, MN, was known as a “crook’s paradise.” Rather than cracking down on bootleggers, the city’s police and politicians made deals to protect criminals in exchange for a share of the profits. This made St. Paul a safe place for gangsters and smugglers moving liquor throughout the Midwest.
The End of Prohibition, But Not the End of Moonshine
Prohibition ended in 1933, but the culture of bootlegging and moonshining never completely disappeared. Many former bootleggers transitioned into legal liquor businesses, while others continued their craft in secret. Even today, the tradition of homemade whiskey lives on in certain parts of the country.
The Prohibition era proved one thing: when people want something badly enough, they’ll find a way to get it.
robert.davis 
Sarah Johnson