Rob TymecDiscovering the hidden stories of the Prohibition Era is no longer limited to the city of Chicago. Windsor, a Canadian city just across the river from Detroit, also played a crucial role in the smuggling of alcohol during the infamous period. In fact, almost 80% of the illegal booze that was transported into the United States came through Windsor. With an exclusive event called Bootlegger Tales on March 17, that Windsor story will be explored.

Windsorites are now embracing their rich history and creating entertainment experiences that give locals and visitors alike a glimpse into the region’s past. The Rumrunner Tour, a bus tour that immerses participants in the world of Prohibition, was the first such venture. Led by guides who dress and act like people from the era, the tour has become a popular attraction in the city.


But some attendees wanted something with a shorter run-time that didn’t require as much movement. That’s where Bootlegger Tales comes in. Created by Rob Tymec, an actor who plays the lead character on the Rumrunner Tour, this show provides a similar experience but in a stationary location.

“I try to cover Prohibition in a different way,” Tymec explains. “I focus on facts that you won’t necessarily get on the tour.” The show has been a hit, with both private and public performances consistently well-attended. And as St. Patrick’s Day approaches, Tymec is incorporating an Irish theme into the performance.

“I am researching the impact bootlegging had on Windsor’s Irish community,” he says. “At the very least, I should be able to give a bit of a bio on one of the more famous bootleggers from the area that came from Irish descent!”

Of course, any discussion of Prohibition-era booze wouldn’t be complete without a whisky tasting. It’s become a tradition when Bootlegger Tales is performed at the Water’s Edge Event Centre. And Tymec is more than happy to play host. “I make sure my knowledge of the Prohibition era is thorough when I present it,” he says. “It stands to reason, then, that I should also drink a lot of whisky in order to make sure I can conduct the tasting effectively!”

Whether you’re a history buff or just looking for a fun night out, Bootlegger Tales is sure to entertain. And with Irish-themed drinks available at the bar, the show is the perfect way to celebrate St. Patrick’s Day while learning about Windsor’s fascinating past.

Bootlegger Tales will be performed at Water’s Edge Event Centre on March 17 at 8 pm. Tickets are priced at $20 each, which includes a whiskey, bourbon, and scotch tasting. It’s the perfect way to celebrate St. Patrick’s Day while learning about the fascinating history of bootlegging in Windsor.

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