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Vaughan St. Jail

Doors Open May 25-26, 2024

Visit Winnipeg’s very own Victorian gaol and hear true crime stories about rapscallions, bootleggers, soiled doves and murderers. Stand in cells that held the undesirables from the Winnipeg General Strike, the infamous Gorilla Strangler, solitary confinement and more! For 50 years this building and the people who passed through it changed both local and Canadian history for the good and the bad. Join us for this unique experience and discover Winnipeg’s darker side of history!

Guided tours will run every 15 minutes starting at 9:00am, with the last tour departing at 4:00pm. Tours will be approximately 75 minutes in length with a maximum of 40 guests. No registration required!

This is the only opportunity to enter the building for the public so don't hesitate, get in line and explore the building or volunteer!

Interested in spending the weekend in jail? Contact Kristen at info@squarepegtours.com so she can get you arrested and into the jail event!

What do volunteers do?
1. Play a Character with a speaking part! Play a role as an important historical person that is connected to the jail between 1881-1930. There is a list of 30+ famous individuals that were a part of this building's history. Kristen will share the list and you can choose, learn about their story and dress up. Most costumes and information is supplied to you. Oh, and your speaking part is only about 5 minutes long!

2. Be an Escort by moving groups of people from one vignette to another. Oh wait, were you thinking I meant the other kind of escort??!! Naw, that would be in the "Play a Character" section.

3. Basement Assistant. This person has a small speaking part and doesn't need to be in "character" for this. You help direct groups to areas in the basement and explain the various cells.

4. Be a Gopher, meaning, moving around the building and checking on the crew, delivering water, food to actors and relaying messages. Also, kitchen tidying.

5. Merchandise Table Crew. We need people who are trust worthy to assist in sales of shirts, books, key chains etc.

6. Counter & Recorder. This person stands at the front door to count people entering the jail and recording those numbers on a spread sheet.

7. Set up & Tear Down Crew. Friday night indoor assembly, Sat & Sun outside set up/tear down, Sunday night tear down and load truck.

8. Attend volunteer meetings. There are usually only 2 meetings in May sometimes an extra meeting if adding new stuff.

9. The After Party! We celebrate our freedom with not 1 but 2 after parties!!! The first one is for just the jail crew and the second one is hosted by Heritage Winnipeg. They have door prizes, a buffet and FYI, we always win for the Best Tour Experience! We think Kristen needs a bigger wall for all the awards!
So, if you still want to participate, send an email to Kristen, the Jailor, at
and we will see you next spring!
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