Riverfront Speakeasy Brings 1920s Glamour, Music and Mystery to Windsor’s Waterfront

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Step into another era this summer as the Riverfront Speakeasy presented by LiUNA!625 transforms Windsor’s waterfront into a stylish open-air experience inspired by the city’s Prohibition-era history, streetcar legacy and vibrant arts scene.

Join us on Saturday, August 22, 2026, from 5 to 10 p.m. at the Legacy Beacon in Michael D. Hurst Legacy Park, 780 Riverside Drive West. This free and family-friendly event invites guests to explore hidden corners of the riverfront filled with interactive art, fortune tellers, live entertainment and immersive experiences inspired by the glamour and intrigue of the 1920s. Families are welcome to come down, explore the site and step into a fascinating chapter of Windsor’s Prohibition history!

Tours of Historic Streetcar No. 351 Display and Exhibition 

Windsor’s Legacy Beacon and Streetcar No. 351 site is operated by Museum Windsor and was nominated for Best Waterfront View in the 11th Annual Best of Windsor-Essex Awards this year by Tourism Windsor Essex Pelee Island. The site offers tours of the historic streetcar and corresponding exhibition tracing the roots of Windsor’s proud transportation history. For the Riverfront Speakeasy, tours of Streetcar No. 351 will be offered from 11 a.m. to 10 p.m.

More to Explore

Beginning at 5 p.m., guests can relax on the Streetcar No. 351 patio — a beautiful 10,000 square-foot space offering picturesque views at water level and from the new viewing platform above the facility — where they can enjoy local wines, craft beers, spirits and Prohibition-inspired cocktails before following the clues to discover the Hidden Speakeasy tucked away along the riverfront.

1920s attire is encouraged for guests looking to embrace the spirit of the evening, but costumes are not required. There is, however, one thing visitors may need: the secret password.

Guests are encouraged to bring a lawn chair or blanket to settle in and enjoy the live entertainment at the Hidden Speakeasy.

Free parking is available directly across from the event on Caron Avenue just south of Riverside Drive in Municipal Lot #23.

Speakeasy Entertainment and Experiences

Streetcar No. 351 patio from 5 to 10 p.m.

  • DJ Bootleg Benny
  • Songstress Tara Watts at 6 p.m. and 8 p.m.

Hidden Speakeasy

  • Mississippi Mike & The South Side Strutters from 5 to 7 p.m.
  • Hugh Leal Speakeasy Quartet from 7:30 to 9:30 p.m.
  • The Bootleg Blaze Show at 9:45 p.m.

Additional entertainment from 5 to 10 p.m.

  • Sleight-of-Hand Artist Eric Bedard
  • Fortunes & Secrets with Madame Kristie Trepanier and Madame Linda Dumouchel
  • Encore Windsor Players

With music, mystery, entertainment and a touch of 1920s intrigue, the Riverfront Speakeasy offers a unique way to experience Windsor’s waterfront!

The Riverfront Speakeasy event is part of the Experience Windsor Riverfront Summer Series presented by LiUNA!625.

Upcoming Riverfront Summer Series event:

Great Canadian Riverfront

  • Dieppe Park and Gardens, 70 Riverside Drive West — Sunday, September 6, 2026

Experience Windsor

Experience Windsor brings parks, waterfront spaces, neighbourhoods, community centres, cultural venues and civic facilities to life through a season-long calendar of free events, entertainment, recreation and community programming.

The Experience Windsor series features three distinct event experience streams:

  • Riverfront Summer Series
  • Staycation Activation
  • Neighbourhood Nights

Together, the three streams offer more than 50 free events and activities throughout the summer and fall, encouraging residents and visitors to explore, connect and experience everything Windsor has to offer. 

For a full list of Experience Windsor events, visit www.CityW.ca/ExperienceWindsor. 

Quote:

“The Riverfront Summer Series has taken us to some incredible locations along Windsor’s waterfront, and this time we are bringing a completely different experience to the Legacy Beacon and Michael D. Hurst Legacy Park. The Riverfront Speakeasy is an opportunity for more residents to discover this unique setting while celebrating Windsor’s colourful Prohibition history, fittingly, at the end of Prohibition Week. With live jazz, hidden surprises and the atmosphere of a 1920s speakeasy, it promises to be a night unlike anything else we have hosted on the riverfront. Keeping affordability top of mind, and with more families choosing to stay closer to home this summer, Council has approved the Experience Windsor initiative to help create opportunities to make great and lasting memories while discovering more of what our city has to offer. Thank you to LIUNA!625, presenting sponsor of the Riverfront Summer Series, for helping us bring these experiences to life, and to our friends at Tourism Windsor Essex Pelee Island for helping build excitement during Prohibition Week. I look forward to seeing folks at the Riverfront Speakeasy!” 
- Windsor Mayor Drew Dilkens

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