Tours through Kingston Penitentiary offer a unique opportunity to go behind the walls of Canada’s oldest and most notorious maximum security prison. Its doors closed in 2013. And now offers guided tours which provide an up-close look at this historical building which predates Canadian confederation.
The first time we went to Kingston in 2013, the Pen was still operating as a maximum security prison.
After some 182 years, I finally got to take a semi-private tour of the formidable Kingston Penitentiary, once home to some of Canada’s worst criminals.
Canada’s Penitentiary Museum
I decided to tour Canada’s Penitentiary Museum located directly across from Kingston Pen. I was happy that I did as the museum explains the history of Kingston Penitentiary and other correctional centres using displays that incorporate artifacts, photographs, equipment, and replicas. The museum also houses most of the institution’s historical records as well as those of other Canadian penitentiaries, and provides the only penitentiary research service in Canada.

“The box” — the notorious upright coffin in which inmates were sealed for hours at a time as punishment. Imagine being confined to this coffin like form of punishment for up to 9 hours?
Below are typical “shivs” or “shanks” which are frequently found in prisons. These items are illegally manufactured by inmates using materials found in trade shops. I am not going to lie, I was a bit impressed with their ingenuity.

I hate to say it, but this was a creatively brilliant escape.
Mugshot chair from Stoneybrook Institution in Winnipeg, MB. Mug Shots were first introduced in 1906. Inmates would place the back of their heads again the round ball. This was necessary for a usable photo to be taken, given it took longer in those days as the camera exposure was quite long.
Kingston Penitentiary
Kingston Penitentiary (known as KP or Kingston Pen) is a former maximum security prison located in Kingston, Ontario, Canada, between King Street West and Lake Ontario.
For nearly 180 years, Canada’s most vicious called Kingston Penitentiary home.
There were killers, thieves, rapists and drug dealers, and headline-grabbing names, such as The Scarborough Rapist and murderer Paul Bernardo, former colonel Russell Williams, Clifford Olson, the child-killing “Beast of British Columbia”, Wayne Boden: The “Vampire Rapist”, Tim Buck: The general secretary of the Communist Party of Canada was convicted of Communist agitation in 1931. Edwin Boyd: The Toronto bank robber and folk hero was jailed in the 1950s. His story inspired the 2011 movie “Citizen Gangster.” Thousands served here. The youngest? An 8-year-old 19th-century bread thief.
KP was constructed in 1833–34. It opened its doors on June 1, 1835 — 32 years before Canadian Confederation, as the “Provincial Penitentiary of the Province of Upper Canada”, it was one of the oldest prisons in continuous use in the world at the time of its closure in 2013. It didn’t become known as Kingston Penitentiary, or KP, until after Confederation in 1867.

Six inmates were accepted when the penitentiary was initially opened. When the first convicts arrived from Toronto in 1835 to serve their time, the new prison was not yet open for business; the inmates had to be held at the county jail for five days.
The original rules for inmates stated that inmates “must not exchange a word with one another under any pretence whatever” and “must not exchange looks, wink, laugh, nod or gesticulate to each other,” with violators receiving the lash. They were literally not allowed to talk all day. It was thought that if they were silent and had time to think of their wrongdoings they would recover and would not reorient once they were released. This just did the opposite, it drove the inmates mad!
Our young guide, shepherds us through the gutted prison. At nearly every turn, a retired guard tells us stories from the facility’s past.
We pass by Private Family Visitation Units: a small row of semi-detached cottages (conjugals) with yards where model prisoners could have barbecues with their kids and catch up with their lovers.
Nearby, there’s a sewer grate where guards would dump confiscated homebrew.
In 1859 – 1861 the centre dome was added connecting all four cell ranges. The facility consisted of a single, large limestone cellblock containing 154 cells in 5 tiers and some outbuildings.

Below, Vern Thibodeau, a former corrections officer (guard) at KP takes part in our tour telling us about centre block and the infamous “bell” that directed each of the inmates movements throughout the day. They apparently HATED that bell and it was the first thing to be destroyed during the 1971 riot.
Vern tells us about the three prison riots. The worst, which occurred in 1971, saw six guards held hostage and two inmate deaths over four harrowing days. Several parts of the prison were so badly damaged in the riot that they never reopened as a cell block.

We moved onto Range 2G1 (they call cell blocks ranges). This was a general population wing. There were two levels to each range and 1 guard area in each section.
The cells originally ONLY measured 29 inches wide by 8 ft deep! Imagine that, not even the width of a standard sized stove! The cells remained the same small size until the first major renovations between 1895 and 1906. Most of the cells have been stripped, but several inmates left their belongings when there were transferred to Millhaven.
The HOLE – solitary confinement – the prison’s dissociation unit. This is where the they housed inmates for their own protection against the general population or to keep them away from from other inmates because they are deemed dangerous. The cells in the unit were larger and private. And unlike normal cells, they had windows and air conditioning, because they were confined to their cells 23 hours per day, only allowed yard use for 1 hour. Their ‘yard’ is not with the general pop yard, they have a very small concrete only area located inside their range. In case you’re curious, Paul Bernardo’s cell was #4 – I don’t think any Canadian is surprised that he’s in solitary confinement for his own protection.
General population yard – south guard tower in the far left corner. At the back right, there is a basketball area/nets. They did have access to weights, but they were eventually removed due to safety concerns.
This is also where Tyrone “Ty” escaped KP. Conn was 32 years old, serving a 47-year prison sentence at maximum-security Kingston Penitentiary when he staged a spectacular escape on May 7, 1999.
His cunning, patience and ingenuity, coupled with a series of stunning security failures, made the breakout from the Bighouse possible. Conn was the first prisoner to make it over the wall of Kingston Pen in 41 years. He scampered over the east wall sometime between 3 a.m. and 5 a.m., strapping and grappling hook he fashioned from a piece of steel rebar.
He made a dummy to act as himself. The crude apparatus was constructed the night before the escape. A shoebox served as torso and paper towel rolls served as an arm and leg.
There was no head.
The limbs and torso were wrapped in towels and hockey pads were placed at the joints.
The dummy was dressed in a T-shirt and track pants. It was positioned in his bunk so that seen from outside the cell, part of the torso and a bent knee and elbow were visible.
The head of the ‘person’ on the bunk wasn’t visible because Conn began using a headboard on his bed several weeks earlier. A guard passing his cell could not see his head.
For weeks, Conn began lying on his bunk in the same position that the dummy would later assume.
The nearest guard tower (the one in this photo at the back of the Yard), a squat observation post at the southeast corner of the prison, had been empty since 11 p.m. the night before. Had a guard been on duty, he or she likely would have had a clear view of the escape in progress, and, armed with a rifle, would have been equipped to stop it. The tower had been unstaffed on the overnight shift for several years, a victim of management budget cuts, despite the protests of prison staff.
After the escape, prison managers reinstated 24-hour-a-day, seven-day-a-week staffing of four perimeter watch towers at Kingston Pen.
Conn’s escape also was successful because two inmate accomplices on his cellblock spent the evening of May 6 moving a dummy in and out of his cell bunk before regular head counts. At the time, Conn was hidden in a canvas shop, assembling his escape gear. The dummy wasn’t discovered until after 7 a.m., when a search of the prison was ordered after a staff member arriving for work noticed the canvas strapping dangling from the outside of the east wall.
Ty Conn’s breakout was embarrassing for senior Corrections officials, who deserved much of the blame for fostering a culture at Kingston Pen that made the escape possible, front-line staff say. The internal inquiry into Conn’s escape and the resulting report documents dozens of security failures at the prison. Many prison workers insist that the final report was a whitewash, meant to protect prison managers and senior Corrections staff. It chronicles the genius of Conn’s escape plot. It does not address one lingering question – who helped him? Police who investigated the escape are nearly certain that an accomplice in a car was waiting outside the prison in a nearby neighbourhood to spirit Conn quickly out of Kingston. That person has never been identified.
“It appears that he ran toward Alwington Place, ripped open an envelope and spread cayenne pepper to throw off the dogs,” Labrash says.
The car may have been parked in the Alwington neighbourhood just east of the prison or perhaps as far east as the Tett complex, adjacent to the prison service’s regional headquarters.
Labrash says there was evidence that Conn ran east along the waterfront to his rendezvous.
The Regional Treatment Centre (RCT) was an independently run facility providing in-house mental health and services to the Ontario regional population.
Work Shop Building – there was a mattress area, a carpentry shop, a fabrication area, tailoring, shoemaking and a metal shop/blacksmithing and right up the stairs – a school. Inmates were paid $5.00 per day to go to school. Which was a relatively high wage. The max an inmate could earn was $6.90 a day. They were able to use his money for canteen items. The higher wage than other work ships was to promote education upon release.

What the Dickens?
Charles Dickens visited Kingston and the penitentiary in 1842, and wrote in his American Notes for General Circulation, “There is an admirable jail here, well and wisely governed, and excellently regulated, in every respect.” He went on: “Here at Kingston is a penitentiary, intelligently and humanely run.” Apparently he wasn’t privy to the brutal conditions prisoners actually endured then.
Eight-year-old Antoine Beauche, for instance, was lashed 47 times in nine months for breaking in-house rules that included staring, laughing, whistling, giggling and idling.
Heamingway Visits KP
On September 11, 1923, on his first day as a reporter with the Toronto Daily Star (now the Toronto Star), 24-year-old Ernest Hemingway was sent to KP to cover a dramatic jailbreak that occurred the day before. His 2,6000-word report detailed the daring escape of five inmates, including burglar Norman “Red” Ryan. Ryan was caught almost a year later while picking up his mail in Minneapolis. He was sent back to Kingston to face 30 lashings and life in prison.
KP Closes Its Doors
Citing aging infrastructure and rising maintenance costs, the federal Government closed KP’s doors in 2013 after 178 years. Inmates were transferred to Millhaven Maximum Security down the way in Bath, Ontario.