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Bootleggers Bash | Celebrating Windsor’s 100 Years of Prohibition History

October 11, 2019 @ 8:00 pm - 1:00 am

Bootleggers Bash Poster

The Bootleggers Bash, celebrating the 100th anniversary of Windsor’s colorful prohibition history, takes place at the Water’s Edge Event Centre on Friday, October 11, 2019.

The Bootleggers Bash is a unique evening of music, libations, performances and Cubanos that celebrates Windsor’s important and colourful role in during Prohibition era. Hosted by the affable gangster “Baby Face Frankie”, guests are invited to arrive in 1920s attire with a prize for Best Dressed Dame and Best Dressed Fella. Performances include Roaring 20s-era live music by Windsor’s own The Music Makers Band and a burlesque dance show by Win City Roses. Cigar cutting demonstration by Humidor 1 Tobacconist. “A Taste of Windsor” signature whisky cocktail and tokens for local whisky, wine and beer tastings are included in the ticket price. Secret password to The Havana Courtyard is also included. In benefit of Family Respite Services of Windsor-Essex.


• “A Taste of Windsor” signature cocktail and four whisky, wine, beer tasting tokens.

• Live music by The Music Makers Band.

• Burlesque dance performance by Win City Roses.

• Cigar demo and sales

• Tastings of local whisky, wine and beer.

• Attire: 1920’s attire encouraged but not required

Tickets are $30 in advance or $35 at the door.

Tickets can be purchased online through Eventbrite

Related Article

Event Review: Inaugural Bootleggers Bash Toasts Windsor’s Close Connection to US Prohibition

Actors Eric Branget and Rob Tymec as Baby Face Frankie during the Bootleggers Bash

Actors Eric Branget (left) and Rob Tymec sharing the role of gangster Baby Face Frankie during the inaugural Bootleggers Bash, a celebration of Windsor Ontario’s 100 year anniversary in connection to US Prohibition, at The Water’s Edge Event Centre on Friday, October 11, 2019. Photo by Robert Tuomi / Eyes On Windsor.



October 11, 2019
8:00 pm - 1:00 am
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Water’s Edge Event Centre
2879 Riverside Drive East
Windsor, Ontario N8Y 4S7 Canada
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