Toronto Through My Lens

The Old Don Jail

Given that my last post was of the Hennick Bridgepoint Hospital, it seems only natural to segue into posting about its next door neighbour – the old Don Jail.

When I first arrived in Toronto many moons ago I remember hearing about the infamous Don Jail from so many different people. To say the place fell into wrack and ruin was an understatement; by all accounts it had all the charm of a medieval dungeon.

Construction & Cramped Quarters

The Don Jail was built between 1858 and 1864, with a new wing built in the 1950s. Designed in 1852 by architect William Thomas, who also designed St. Michael’s Cathedral and St. Lawrence Hall, the jail was constructed with a distinctive facade in the Italianate style.

The Don Jail opened in 1864 and closed in 1977. The Jail was state-of-the-art when it was built, and considerably more humane than jails in much of the world at the time. It was certainly a great improvement from earlier Toronto Jails. The cells, though, were tiny – just 86 centimetres wide and there was no electricity or plumbing. A bucket served as a toilet, which was emptied every morning.

Prisoners were not allowed to talk without permission and received only monthly visits from friends and family. Violations frequently resulted in flogging. For about the first 100 years, inmates generally were not allowed to speak unless addressed first by a prison official.

Prisoners spent 23 hours a day in the cell blocks with the remaining hour in the outdoor exercise yard, now a parking lot. They had to keep moving in the yard and were not allowed to sit around and soak up the sun. The inmates did much of the maintenance including painting, carpentry work and other jail repairs. They also worked a jail farm that covered much of the present Riverdale Park.


In later years the Don Jail became extremely overcrowded. Frequently three inmates were held in cells meant for a single prisoner and in other cells inmates went for days without a chance to exercise. The environment was so bad that both prisoners and guards were at risk. The jail did not meet the minimum prison standards of the United Nations.

At one time the jail held 691 prisoners, well over the recommended maximum. It was designed to house 275 prisoners, one per cell, and it was noisy and plagued with mice and cockroaches. Many of the prisoners suffered from mental illness.

Public Hangings

Public hanging in Canada wasn’t abolished until 1869, and in Toronto it was moved indoors from the Don Jail yard to its confines in 1905. Before capital punishment was abolished in Canada, the Toronto Jail was the site of a number of hangings. Starting with the execution of John Boyd in January 1908, hangings at the jail took place in an indoor chamber, which was a converted washroom, at the northeast corner of the old building.

Previously, condemned men had been hanged on an outdoor scaffold in the jail yard. The indoor facility was seen as an improvement because outdoor executions were quasi-public (at the hanging of Fred Lee Rice on July 18, 1902, crowds had lined surrounding rooftops to see something of the spectacle), and because the condemned didn’t have to walk as far.

A Massive Renovation

When the Hennick Bridgepoint Hospital demolished the 1950s-era Riverdale Hospital building to replace it with a new 10-storey facility, the historic Don Jail building was extensively renovated to serve as the administrative wing for the hospital, a process which included the removal of “150 years worth of grime” from the exterior. About 20 per cent of the former jail’s heritage interior was preserved, including the centre block’s half-octagonal rotunda featuring clerestory windows, as well as original iron railings and balconies supported by griffin and serpent cast-iron brackets.

In 2012, Bridgepoint Health commissioned a complex restoration project to be carried out on the Don Jail, overseen by several architecture firms. The inflexible floor plan, established for the isolation and separation of prisoners, was transformed into an open, welcoming, and functional administrative space for the new Bridgepoint Active Healthcare Centre.

About 20 per cent of the former jail’s heritage interior was preserved, and the rest of the brickwork cleared out to make way for modern office space. Clear material distinctions were made between new and old and the patina of history. A new partition never meets an old wall, but instead is separated by a glass fin and the marks of history. This work was recognized with the 2016 Built Heritage Award of Excellence.

Hennick Bridgepoint Hospital coupled with the Old Don Jail

The east wing was formally decommissioned on January 6, 2014, at which point it too was transferred to Bridgepoint Health and demolished in March and April of that same year. The grounds of the former jail are being landscaped into a city park to be named Hubbard Park after William Peyton Hubbard. The former Don Jail Roadway has been extended and renamed Jack Layton Way after Jack Layton, the late leader of the New Democratic Party of Canada and former Member of Parliament for the area.

On A Final Note, Literally…

Those who know me know I’ll link pop music to anything, and the Don Jail is no exception. Most of us from the music video era know that a certain Canadian pop star who liked to wear sunglasses at night shot his 1984 signature video at the old Don Jail. This was way, waaaaay before its current renovated state of course:

OK, queue the pulsating synths…


There are practically hundreds of articles written on the history of the Don Jail. The information above was gleaned from several websites, the City of Toronto and the Ontario Heritage Foundation by the Toronto Historical Board.

For an interesting 2011 article from The Globe & Mail regarding the Don Jail, click here. The piece highlights much of the harrowing and inhumane conditions in the jail during its prime.

1 Comment

  1. David

    Love The Don Jail! Got to see it during Doors Open one year
    Good post !

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