A Peek Inside Canada’s Oldest Prison – Kingston Pen Tour Review


For a city that has produced iconic Canadian talents such as Bryan Adams and The Tragically Hip, it’s odd to say that the hottest ticket in Kingston is for a prison. Since opening its doors to tourism in 2016, visiting Kingston Penitentiary has been in high demand and often sells out its daily tours well in advance. Admittedly, I knew very little about the prison so was a bit confused by this attraction. It is, after all, just a really big and really old jail.

To better understand what all the fuss is about I took a peek inside.

Can a Prison be Beautiful?

Apparently, yes.

The first thing that struck me about visiting Kingston Penitenteray is the beauty of the building itself. This is an odd thing to say about a prison however much like the rest of old Kingston, it is made of limestone. From the courthouse to the towers that once protected Kingston’s shores, “Stone City” has its share of beautiful structures. Kingston Penitentiary is, oddly, one of them.

The second thing I noticed while visiting Kingston Penitenteray is its surprising location on the shores of Lake Ontario. The beauty of this waterfront location is lost when passing by the entrance on King street however it’s land value should be clear with the Portsmouth Olympic Harbour, home to the sailing events from the 1976 Summer Olympics, neighboring the prison to the west. Thanks to Fly Kingston I was able to get a bird’s eye view of Kingston Pen and only made me question it’s location further. Why anyone would build a prison here and give up this water-front property was beyond me, but again, that is why I was taking this tour.

Touring Kingston Pen

NOTE: There are 2 types of Kingston Pen tours; a one-hour standard tour (offered in French or English) and a  2 1/2 hour premium tour. The latter takes you deeper inside the penitentiary and looks at the criminological components on top of the architecture and history. Both can be booked here.

Built in 1833, Kingston Pen was Canada’s first maximum-security prison and served as such until closing its doors in September 2013. Its waterfront location was chosen as for its easy access and abundance of limestone. At the time of construction, Kingston (and much of Ontario) was not developed so little thought was required in giving up prime real estate. Makes sense I suppose. Those views though…

At the time of closure, Kingston Pen was one of the oldest prisons in continuous use in the world. During that time it held some of Canada’s most notorious criminals including Clifford Olson, Russell Williams, and Paul Bernardo…although you would never know that taking this tour. At the very beginning of the tour, our guide was quick to point out that he is legally not allowed to answer specific questions on former inmates due to Canada’s Privacy Act. This was nice as, in a way, it avoids making a celebrity out of the criminals that served there. Instead, the tour focuses on the history behind the building and why it is so important in Kingston’s story.

Behind the Walls

Once I signed my life away through a mountain of waivers, our tour began with a walk through the main courtyard. This took us past the conjugal visit units and past the center where the inmate radio show was broadcasted from. So far life inside Kingston Pen didn’t seem that rough. Less so when we were told that inmates in the conjugal visit units could order-in pizza or Chinese food. From my limited knowledge of life behind bars (supplied by films and TV shows), this is not what I expected.

Behind the Scenes

This theme continued throughout the day with our guide noting the differences between Hollywood and real life inside the jail. He also pointed out the differences and flaws with the private jail systems in the States versus the government run institutions in Canada. Thankfully privately run prisons have been limited and reverted to Government control in Canada.

Our tour continued inside the prison where we were handed off to a retired guard who filled us in on what life was like day-to-day for both the prisoners and himself. This was an incredibly interesting touch and similar to what you will find on the audio guides of Alcatraz as well as the personal stories from the former prisoners of Robben Island in South Africa.

We were then allowed to stroll through a wing of mocked up cells, again not being told what notorious criminal was locked up where. This is where the prisoners spent most of their time, including where they ate their meals.

Personally, what I found most interesting during my time visiting Kingston Pen was the workshop and the brick building it was housed in. As Kingston pen was a working prison the labor shop produced everything from mattresses to furniture. Because the inmates made roughly $6 a day, the products were only ever used in other government agencies.

Riot Revealed

The former guard also went through the conditions that led to the 1971 riot; a four-day event that resulted in hostages, police negotiations, and fires. In the end the inmates gave in after the military showed up and threatened to take the prison back with force. Two prisoners were killed during the riot and much of the prison was damaged beyond repair, partially because the inmates were concerned about moving to the newly built Milhaven facility.

Like I said, this place is oddly beautiful. Clearly, those that spent the most time in it, knew this.

The Most to Canadian Escape Ever

One former inmate story that the guide did share was of Norman “Red” Ryan, one of only a handful of prisoners to ever escape Kingston Pen. After setting fire to a barn as a distraction, “Red” and a small group of prisoners made their move over the tall stone walls. During his escape he fought off a guard, hitting him in the head with a pitchfork to shake free. Although in the clear for some time, hurting the guard weighed heavily on Ryan to the point of writing an apology and mailing it to the guard, return address and all. Days later Ryan was able to apologize in person.

How’s that for a true Canadian escape artist? Only getting caught because he said sorry.

What makes this story that much more amazing is the fact that a young Ernest Hemmingway, on his very first day working for the Toronto Daily Star, was sent to Kingston to cover the escape. You can read his story here.

Worth the Visit. Worth the Wait

In the end, touring Kingston Pen is a great way to appreciate and understand Kingston’s connection to corrections. Paired with the Penitentiary Musem across the street, visiting Kingston Pen offers an amazing insight into life inside Canada’s oldest prison and judicial system. With its architectural highlights and the intrigue of seeing something hidden from the public for over 180 years, touring Kingston Pen is a must do when visiting the area. Again, this tour is popular so be sure to book ahead!


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Although I was provided a complimentary day touring Kingston Pen thanks to Visit Kingston,
the experience, opinions, and realization that prisons can be pretty are my own.


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  • Wallis

    Haha I laughed at the story about the Canadian prisoner who escaped and then apologized :p The exterior of the prison looks really beautiful by the way!

  • Looks Like an Interesting Fully Escorted Guided Tour Provided by Kingston Pen Tours for Those Visiting Ontario, Canada. Canada’s Version of Alcatraz Prison in San Francisco!

  • Lisa Rivera

    Another prison that’s become a point of interest, so interesting, and Kingston Pen is one to see for sure!

  • Dinh-Long

    Wow… it actually looks like a university from the outside! I guess it’s interesting to see how is the life inside the prison, far from the Hollywood stuff! And having a former guard as a speaker really makes it interesting.

  • What a cool trip, I’d love to do something like this at a prison! Bet it was really interesting x

  • Medha Verma Bector

    I have never been for a prison tour but I can imagine how cool it must have been! Love the pictures and I bet the guides have some very interesting stories to tell about things that have happened there. What a cool thing to do!

  • Thank you for such a detailed report, Shaun. You make the tour sound very interesting. Worth a visit for sure.