Windsor Steps Back in Time for Prohibition Week August 17–23
Week-long celebration brings Windsor’s legendary rum-running history to life through tours, tastings, cultural experiences and the free Riverfront Speakeasy
WINDSOR, ON – This August the City of Windsor and Tourism Windsor Essex Pelee Island are turning back the clock to one of the most fascinating chapters in Windsor’s history.
From August 17 through 23, Prohibition Week will invite residents and visitors to discover the people, places and stories that helped make Windsor one of North America’s most legendary Prohibition-era destinations. The week will feature a collection of specially curated tours, historical experiences, tastings, film, entertainment and exclusive activities offered at discounted rates or free of charge. Visitors can learn more at www.visitwindsoressex.com/prohibitionweek.
The celebration culminates on Saturday August 22, with the Riverfront Speakeasy at the Legacy Beacon, a free Experience Windsor event bringing the spirit of the Prohibition era to Windsor’s waterfront.
Long before Windsor became known as a destination for food, drink and entertainment, its location along the Detroit River placed the region at the centre of the Prohibition story. Rum-running routes, historic distilleries, secret speakeasies and larger-than-life personalities created a legacy that continues to shape Windsor’s identity today.
“Windsor’s history is filled with remarkable stories, and Prohibition is one of the chapters that truly sets our city apart,” said Windsor Mayor Drew Dilkens. “By bringing that history to life through events and experiences, we’re giving residents and visitors new ways to connect with our past while activating our cultural assets, neighbourhoods and waterfront. This is the type of work envisioned through Windsor Works, building on the strengths and assets that make Windsor unique to create a more vibrant city, support economic growth and give people even more reasons to experience everything Windsor has to offer.”
Prohibition Week is supported through the City of Windsor and aligns with Windsor Works, the City’s economic development strategy focused on positioning Windsor for long-term growth by leveraging local strengths, investing in quality of place, supporting tourism and economic activity, and creating a city that attracts residents, visitors, talent and investment.
“Windsor Works recognizes that a strong economy is about more than investment attraction—it’s also about creating vibrant places and experiences that showcase what makes Windsor unique,” said Jelena Payne, Deputy CAO & Commissioner Economic Development, City of Windsor. “Prohibition Week brings our history, culture, tourism and entertainment sectors together in a way that animates our community, supports local businesses, and encourages residents and visitors to explore the city. By offering many of these experiences for free or at reduced rates, we are helping residents and visitors connect with Windsor’s rich heritage while advancing the Windsor Works vision of a dynamic, welcoming and destination-focused city.”
Throughout the week, participants can explore a variety of Prohibition-themed programming across the city:
- Monday August 17: Rum Runners Tour & Willistead Manor and the new Coach House Historical Exhibition Tours
- Tuesday August 18: Free Museum Day at Museum Windsor – Chimczuk Museum & Willistead Manor and the new Coach House Historical Exhibition Tours
- Wednesday August 19: Walkerville District Walking Tour
- Thursday August 20: J.P. Wiser’s Experiences Tours & Tastings
- Friday August 21: Windsor Premier Cruises Prohibition Boat Cruise & WIFF screening of The Great Gatsby
- Saturday August 22: Riverfront Speakeasy at the Legacy Beacon – Free Admission
Experience the glamour and intrigue of the 1920s at the Riverfront Speakeasy on August 22, as Windsor’s waterfront is transformed into a stylish open-air celebration of the region’s Prohibition history, streetcar legacy, and vibrant arts scene. Guests will enjoy live jazz, vintage cars, interactive experiences, roaming performers, local spirits, and sophisticated lounge spaces, all set against the stunning backdrop of the Detroit River. Vintage attire is encouraged, and visitors can watch for a secret password-only cocktail to complete the authentic speakeasy experience. Admission is free, and everyone is invited to join us at Legacy Beacon, Michael D. Hurst Legacy Park for an unforgettable evening of history, culture, music, and entertainment.
All-week experiences will also include the Barrels Bottles & Brews Trail Prohibition Week Flight Log, cocktail specials at select participating “speakeasies,” exploring the history through the CROSSROADS Historical Guide, and exclusive discounts unlocked with a special Speakeasy Password at local small businesses valid between August 17-23.
“Cultural tourism is about giving visitors an authentic connection to the stories that make a destination different, and Windsor’s Prohibition history is an incredible asset that is uniquely ours,” said Gordon Orr, CEO Tourism Windsor Essex Pelee Island and CEO, Invest WindsorEssex. “We have the history, the distilling legacy, the Detroit River and the places where many of these stories actually unfolded. Prohibition Week packages those assets into experiences that can inspire travel, encourage visitors to explore more of Windsor and create new economic activity for our tourism partners. It’s a great example of how we can take our history and turn it into a compelling reason to visit today.”
Whether you’re a history enthusiast, whisky lover or simply looking for a unique way to experience Windsor, Prohibition Week offers an opportunity to uncover the stories, characters and places behind one of the most colourful eras in the region’s history.
Many Prohibition Week activities are available at and exclusive discounted pricing or in some instances for free, with advance registration required for select experiences. Tickets are available now for select events at www.visitwindsoressex.com/prohibitionweek.
