Old Don Jail – Toronto’s Intimidating & Imposing Prison on the Hill

2019 - The Old Don Jail now Bridgeport Active Healthcare administrative offices, looking northeast
2019 – The Old Don Jail now Bridgeport Active Healthcare administrative offices, looking northeast

The Old Don Jail is located at ‪550 Gerrard St E‬ (at Broadview Ave) in the Riverdale neighbourhood of Toronto.

Scadding Family Homestead

In 1856, the City of Toronto purchased the northern half of the Scadding family property. The 119 acres of land were bounded by Gerrard St E, the Don River, a line south of Danforth Ave and Broadview Ave. Then just beyond the City limits, the property was purchased to establish a hospice, industrial farm and a jail.

Construction Delays

Taking five years to build, the Don Jail opened in 1864. Construction was delayed due to the death of head architect William Thomas in 1860 and a significant fire in 1862. The imposing structure was, at the time, located on a hill just outside of the City limits. The Renaissance Revival-style building was designed to look intimidating. Mr Thomas also designed other Toronto landmarks, including St Michael’s Cathedral Basilica and St Lawrence Hall.

The Architecture and Life at the Old Don Jail

1973 - The Don Jail and Metropolitan Toronto Jail
1973 – The Don Jail and Metropolitan Toronto Jail

The 4-storey centre block is flanked by 3.5-storey east and west wings. Some of the features of the brick and stone structure include iron, wood and stone trim, a hipped roof, gables and an arched entrance flanked by banded columns. The tall entrance doors with Father Time above cast its gaze down, daunting those that passed beneath.

The jail, Toronto’s fourth, attempted to provide an appropriate setting that embodied the progressive ideas of prison reform. Some of the original 180 cells only measured 1×3 m or 3×10 ft, and since the cells had no plumbing, a bucket was supplied for bathroom use. The governor’s quarters were later converted to cells bringing the total cells to 220. Overcrowding was often an issue at the jail.

The walls around the yard were towering, 5.5 m or 18 ft high. Inmates worked a farm behind the prison, now Riverdale Park East. Two 20-minute visits were permitted each week. The last execution occurred in 1962; however, there were over 30 executions at its gallows.

In 1973, the older portion of the Don Jail received heritage status and was closed four years later.

Haunted Tales

The notorious building is said to be haunted by many ghosts. They include those who have been executed, murdered or committed suicide. One such spirit is said to be that of an angry female inmate who hanged herself in her cell. It’s rumoured that her apparition has been seen in the central rotunda.

In 2007, the skeletal remains of 15 people interred behind the Old Don Jail were unearthed. They were those of prisoners sent to the jail’s gallows. Click for more haunted tales.

Bridgepoint Active Healthcare

2021 - Bridgepoint Active Healthcare and the Old Don Jail, looking northeast
2021 – Bridgepoint Active Healthcare and the Old Don Jail, looking northeast

Today, the administrative offices for Hennick Bridgepoint Hospital now occupy the space of the historic Old Don Jail. When walking around the significant property, visitors can find many plaques detailing the site’s history.

Did You Know?

  • York’s first jail was located on the south side of King St E, between Toronto and Victoria St from 1798 to 1824. It’s on the site of the present-day King Edward Hotel.
  • From 1824 until 1840, the second jail was located on the northeast corner of King St E and Toronto St.
  • Toronto’s third jail was on the south side of Front St E between Berkeley and Parliament Sts from 1840 to 1860’s.
  • The 19th century, the word “jail” was spelled the British way “gaol”. They are both pronounced “jail”.
  • The Scadding family were early settlers of York. The Scadding Cabin is the oldest known structure in Toronto.
  • In 1958, the east wing known as the Metropolitan Toronto Jail was added. This section of the jail was closed in 1973. It was later demolished and now serves as a parking lot.
  • In 1973, the older portion of the Don Jail received heritage status.

Old Don Jail Photos

1949 - The centre block and entrance of the Don Jail, looking northeast
1949 – The centre block and the entrance of the Don Jail, looking northeast
2019 - The Old Don Jail now Bridgeport Active Healthcare administrative offices, looking northeast
2019 – The Old Don Jail now Bridgeport Active Healthcare administrative offices, looking northeast
2020 - Centre block and entrance of the Old Don Jail, now Bridgepoint Active Healthcare administrative offices
2020 – Centre block and the entrance of the Old Don Jail, now Bridgepoint Active Healthcare administrative offices
2021 - Entrance of the Old Don Jail, now Bridgepoint Active Healthcare administrative offices
2021 – Entrance of the Old Don Jail, now Bridgepoint Active Healthcare administrative offices
2021 - Father Time keystone over the entrance of the Old Don Jail
2021 – Father Time keystone over the entrance of the Old Don Jail
2022 - Looking northeast towards the Hennick Bridgepoint Hospital at 1 Bridgepoint Dr, and the Old Don Jail at 550 Gerrard St E
2022 – Looking northeast towards the Hennick Bridgepoint Hospital at 1 Bridgepoint Dr, and the Old Don Jail at 550 Gerrard St E
2022 - Looking southwest towards the back of the Old Don Jail
2022 – Looking southwest towards the back of the Old Don Jail
2022 - Top of the rotunda along with the skylights and barred windows at the Old Don Jail
2022 – Top of the rotunda along with the skylights and barred windows at the Old Don Jail
2022 - Bars on a window of the Old Don Jail
2022 – Bars on a window of the Old Don Jail
2020 - Back of the Old Don Jail, now Bridgepoint Active Healthcare administrative offices, looking southwest
2020 – Back of the Old Don Jail, now Bridgepoint Active Healthcare administrative offices, looking southwest
2020 - The Don Jail heritage plaque
2020 – The Don Jail heritage plaque
2021 - Back of the Old Don Jail, now Bridgepoint Active Healthcare administrative offices, looking southwest
2021 – Back of the Old Don Jail, now Bridgepoint Active Healthcare administrative offices, looking southwest
2021 - The Governor's House and the Old Don Jail, looking northwest
2021 – The Governor’s House and the Old Don Jail, looking northwest
2021 - The Gate Keeper's House and the Old Don Jail, looking northeast
2021 – The Gate Keeper’s House and the Old Don Jail, looking northeast
2021 - Gatekeeper's House heritage plaque
2021 – Gatekeeper’s House heritage plaque
2021 - The Old Don Jail, Governor's House and Gatekeeper's House
2021 – The Old Don Jail, Governor’s House and Gatekeeper’s House
2021 - Bridgepoint Active Healthcare and the Old Don Jail, looking northeast
2021 – Bridgepoint Active Healthcare and the Old Don Jail, looking northeast
1973 - The Don Jail and Metropolitan Toronto Jail
1973 – The Don Jail and Metropolitan Toronto Jail
1952 - Mayor Allan Lamport entering the Don Jail after a jail break (City of Toronto Archives, Globe and Mail Fonds, Fonds 1266, Item 148252)
1952 – Mayor Allan Lamport entering the Don Jail after a jailbreak (City of Toronto Archives, Globe and Mail Fonds, Fonds 1266, Item 148252)
1952 - Major John Foote inspecting a cell door after a jail break at the Don Jail (City of Toronto Archives, Globe and Mail Fonds, Fonds 1266, Item 148381)
1952 – Major John Foote inspecting a cell door after a jailbreak at the Don Jail (City of Toronto Archives, Globe and Mail Fonds, Fonds 1266, Item 148381)
1952 - A cell, bed and plumbing at the Don Jail (City of Toronto Archives, Globe and Mail Fonds, Fonds 1266, Item 148383)
1952 – A cell, bed and plumbing at the Don Jail (City of Toronto Archives, Globe and Mail Fonds, Fonds 1266, Item 148383)
1952 - Back of the Don Jail after a jail break (City of Toronto Archives, Globe and Mail Fonds, Fonds 1266, Item 148378)
1952 – Back of the Don Jail after a jailbreak (City of Toronto Archives, Globe and Mail Fonds, Fonds 1266, Item 148378)
1952 - The Boyd Gang being escorted to City Hall from the Don Jail (City of Toronto Archives, Globe and Mail Fonds, Fonds 1266, Item 148365)
1952 – The Boyd Gang being escorted to City Hall from the Don Jail (City of Toronto Archives, Globe and Mail Fonds, Fonds 1266, Item 148365)
1923 - View of the Don Jail and construction of the Gerrard Street bridge from a sheet metal products building, looking northeast
1923 – View of the Don Jail and construction of the Gerrard Street bridge from a sheet metal products building, looking northeast
1915 - The Don Jail with "Toronto Gaol" sign
1915 – The Don Jail with “Toronto Gaol” sign
1885 - Demolition of Toronto's third jail (1840 to 1860), once located on the south side of Front St E between Berkeley & Parliament Sts (Toronto Public Library r-4522)
1885 – Demolition of Toronto’s third jail (1840 to 1860), once located on the south side of Front St E between Berkeley & Parliament Sts (Toronto Public Library r-4522)
1800's - Sketch of Toronto's third jail (1840 to 1860), once located on the south side of Front St E between Berkeley & Parliament Sts (Toronto Public Library r-4518)
1800’s – Sketch of Toronto’s third jail (1840 to 1860), once located on the south side of Front St E between Berkeley & Parliament Sts (Toronto Public Library r-4518)
1835 - Sketch of Toronto's second jail (1824 to 1840), once located on the northeast corner of King St E & Toronto St (Toronto Public Library r-269)
1835 – Sketch of Toronto’s second jail (1824 to 1840), once located on the northeast corner of King St E & Toronto St (Toronto Public Library r-269)
1800s - Sketch of York's first jail (1798 to mid 1820s) at King St E & Leader Lane, southwest corner
1800s – Sketch of York’s first jail (1798 to mid 1820s) at King St E & Leader Lane, southwest corner (Landmarks of Toronto Volume 1 by J Ross Robertson)
2020 - York's First Jail heritage plaque located on King St E & Leader Lane, southwest corner
2020 – York’s First Jail heritage plaque located on King St E & Leader Lane, southwest corner
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