Step back in time to experience Windsor’s legendary history during the prohibition era.
The City of Windsor and Tourism Windsor-Essex Pelee Island (TWEPI) will be hosting Prohibition Week from August 17 through 23, and will invite residents and visitors to discover the people, places and stories that helped shape Windsor’s rum-running history.
The announcement was made Tuesday afternoon in front of the Hiram Walker Commemorative Sculpture.
Windsor was one of North America’s most legendary prohibition-era destinations due to its location along the Detroit River.
The week will feature a collection of tours at Willistead Manor and the Chimczuk Museum, as well as tours of the Walkerville District and J.P. Wiser’s. The week will also feature a Windsor Premier Cruises Prohibition Boat Cruise, and a WIFF screening of The Great Gatsby.
To complete the week, a Riverfront Speakeasy will be held at the Legacy Beacon which will include live jazz, vintage cars, interactive experiences, and more. Vintage attire is encouraged, and visitors can watch for a secret password-only cocktail to complete the authentic speakeasy experience.
Gordon Orr, CEO of TWEPI, says it was a group effort with Windsor.
“So when we were looking at this, we partnered with them and everybody started talking about ‘well, this could be a win’, we could do something that was identified in Windsor Works, and at the same time we could enhance the Experience Windsor program that’s being offered. And mostly, and more importantly, we can celebrate something that’s unique and authentic to Windsor - which is our prohibition history.”

He says there will be events all week long.
“The Signature Experience, of course, is on August 22, and that’s the Riverfront Speakeasy, it’s down at the Legacy Beacon. Other things are, we’ve got the Rum Runners Tour that are doing something special, we’ve got Windsor Premier Cruises doing something special, we’ve got J.P. Wiser’s Event Centre doing something special, we’ve got Chimczuk Museum doing something special.”
Orr says it’s important to remember our past.
“Hiram Walker was a visionary, and he really created the Walkerville District and that it now what we celebrate as the Walkerville Distillery District. When people are looking for places to go, and things to do and see, they’re looking for those authentic immersive experiences... this is exactly ours.”
Prohibition Week is supported through the city’s Experience Windsor initiative, and paid for through the Municipal Accommodation Tax.
Council approved $500,000 at the end of May to put toward events and activities to give people something to do considering affordability challenges Canadians are facing.
More information on the week-long events can be found on the TWEPI website.
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
