Here are some of the key milestones in the history of our neighbourhood centred on the Ashbridge Estate in Toronto’s east end.
If you have more to add (or correct), please comment below. I will be updating this page as I uncover more material; over time I plan to add more links to source material. – Robert Miller
Native peoples were living on the site of the Ashbridge Estate, as shown by archaeological digs carried out in the late 1980s and late 1990s, including a possible late Paleo-Indian point dating to approximately 6000 B.C.
500 A.D. to 1400 A.D.
More evidence of Native inhabitants – other archaeological finds include various ground stone tools, several projectile points ranging from c. 500 A.D. and distinctive Pickering Tradition ceramics from around 1300 to 1400.
Ashbridge family arrives in York from Pennsylvania – widow Sarah Ashbridge with two sons and three daughters. It’s believed they scout the Ashbridge site in 1793 but spend the winter of 1793-94 living in York (which at the time was the area around present-day King Street East and Jarvis/ Sherbourne.)
According to Ashbridge family history, a member of the family blows a conch shell as they enter the bay which came to be known as Ashbridge’s Bay. The family starts to clear land and build a log cabin on the Ashbridge site. The cabin is built on the east side of Ashbridge’s Creek, which is now underground but where the hollow is on the Ashbridge Estate property. Lady Elizabeth Simcoe, wife of Lieutenant Governor Simcoe, in her diary writes of “Pennsylvanians” living beyond the Don River. The extended Ashbridge family has 600 acres – three lots, numbers 7, 8 and 9 – which today is the area from Greenwood to Coxwell, from Danforth south to Ashbridge’s Bay / Lakeshore Boulevard.
In her diary, Lady Simcoe describes visiting Mrs. Ashbridge at the “Settlement below the Town.” The Ashbridges, among the first settlers east of the Don River, are pathmasters of the Bay Road beyond the Don. (This rough path later became Kingston Road from the Don eastward, then later still was renamed Queen Street East.) Ashbridge farm lane follows the route of the current Woodfield Road. The family continues to clear the land and develop their farm.
1790s to 1860s
The area is known as Ashport; the bay, much larger then, becomes known as Ashbridge’s Bay. The bay has a small cove where boats put in, hence Ashport (where the TTC streetcar yard is now). Ashport is a stop on the carriage route along Kingston Road to points east.
Ashbridges build a frame house on the east side of Ashbridge’s Creek, immediately south of log cabin – foundation still exists, currently a rock garden. Ashbridge’s Creek flows from north to south on the Ashbridge farmland (the creek flows from north of present-day Danforth, south through present-day Monarch Park, to Ashbridge Estate).
City of Toronto is incorporated. East of the Don River the city includes the Liberties, south of Queen (at the time still known as Kingston Road).
English writer Anna Jameson wrote in the spring of 1837, about the Ashbridge’s Bay marsh: “this marsh, intersected by inlets and covered with reeds, is the haunt of thousands of wild fowl, and of the terrapin, or small turtle of the lake; and as evening comes on, we see long rows of red lights from the fishing boats gleaming across the surface of the water, for thus they spear the lake salmon, the bass and the pickereen.” Source: University of Toronto Library.
New one-storey brick house built in Regency style (second floor added in 1899). This is the existing Ashbridge house at 1444 Queen Street East.
Grand Trunk Railway opens, cutting across the north end of the Ashbridge farm (railway still there)
Until the late 1850s, a sandbar stretched continuously from Ward’s Island (Toronto Island) to Woodbine Beach, separating Ashbridge’s Bay from the lake. In 1858, a winter storm breached the sandbar, separating the Toronto Islands from the peninsula.
Source: University of Toronto Library.
Ashport post office opens at Queen and Curzon. Postmaster is William Lambert, who had married Amy Ashbridge in 1854. Renamed Leslie Post Office in 1862 after George Leslie took over as postmaster. 1866 Globe newspaper has first reference to Leslieville: along Kingston Road (now Queen East) in the area near Jones and Leslie, 1 kilometre west of the Ashbridge Estate. Leslieville extended up to just north of present-day Dundas St. East.
Thomas Beatty house built, still at 6 CherryNook Gardens. Thomas Beatty worked for the Ashbridges as their farm manager. Since 1985 this is a home of Innstead Housing Co-operative – see a photo on their site.
Horse-drawn trams started running on June 9, 1875 along the Kingston Road Tramway (Queen Street east of the Don River was called Kingston Road at this time) from the Don River to gravel pits west of what is today the Kingston Road-Main Street intersection. Source: Queen streetcar history.
Riverside and Leslieville annexed to the City of Toronto (area west of Greenwood Avenue to the Don River). The term Riverdale starts to be used for the area from the Don to Greenwood, the term Midway for the area between Greenwood and Kew Beach/Norway. Around this time, Kingston Road is renamed Queen Street East, keeping the Kingston Road name north from Queen Street (east of Coxwell), as today.
Ashbridges add second floor to their home (current house at 1444 Queen Street East)
Photos taken by W.T. Ashbridge show the Ashbridge area is still farmland. The family continued to farm as well as operating brickyards. Greenwood Avenue had 10 or more brickyards between the 1860s and the 1920s. For example, 100 Greenwood Avenue was a Price home – the Price family being one of the local brickmaking families. One of the Price clan married a woman named Kerr — Kerr Road is named after her.
Ashdale Public School opens on Ashdale Avenue north of Gerrard (renamed Roden Public School in 1910). Ashdale used to denote the back fields of the Ashbridge Estate. Around this time, Vancouver Avenue becomes the new name for what had been Ashport Avenue.
Midway district annexed by the City of Toronto, including the Ashbridge Estate (strips along Greenwood and Queen had been annexed earlier, and the area south of Queen had been part of the City’s Liberties since 1834).
The Ashbridge family sold the vast majority of their land — all but the current Ashbridge site along Queen, which they occupied until 1997. They sold their orchard for the construction of Duke of Connaught School, and the Ashdale (back fields) for housing. Dozens of the current houses were built in 1912 – 1914. The area was marketed to potential homebuyers as the “Ashbridge Estate.”
November 30, 1911
The Duke of Connaught turned the sod on the site of Duke of Connaught School, then on Morley Avenue (later renamed Woodfield Road). The Duke was the Governor-General of Canada, a son of Queen Victoria.
Duke of Connaught school opens. W.T. Ashbridge publishes family history which describes the sale of the land for construction of the school. To the west: Leslieville school; to the east Norway school. Coxwell Avenue residents are listed in city directories under “Norway.”
Major changes in the east end – as well as housing developments on the Ashbridge Estate, much of Ashbridge’s Bay was filled in for industrial purposes (the two remaining water areas are the current Ashbridge’s Bay and the Ship Channel south of Comissioner’s Street).
Streetcar yard opens at Queen East and Connaught Avenue — still there. Known as the “car barns” or “Connaught Yard,” the official name is the Russell Division. Woodbine Theatre opens at 1383 Queen East, currently empty, formerly home to Stop’N’Go store.
Autodrome opens northwest of Queen and Greenwood, featuring motorcycle and bicycle racing (now site of the Greenwood Court apartments).
East Riverdale Recreation Centre opens at 1511 Queen Street East near Kent Road (in current Jonathan Ashbridge Park; the centre was a hub for the community until it was demolished in the 1950s and replaced by S.H. Armstrong Community Recreation Centre at 56 Woodfield Road).
In a Star Weekly article, the principal of Duke of Connaught describes how he first had some trepidation about moving to a new school in the Midway district, which was considered to be in the middle of nowhere. Other areas to the west and east were more built up while the Ashbridges had continued to farm for much longer. However, it turned out there was no shortage of students. In the years since 1912 the area experienced a building boom, as the Ashbridges sold off much of their land for new housing developments. Many of the new homes were occupied by large families, with the student population growing rapidly at Duke and Roden schools.
Greenwood Park opens on former brickyard site.
Small’s Pond on Queen Street east of Coxwell is drained and streets are extended across its ravines (Orchard Park area). See this photo story: A brief history of Small’s Pond – used then abused
Coxwell streetcar route inaugurated between Queen and Danforth. Woodbine Theatre at 1383 Queen East is renamed the Woodbine Palace.
Gerrard-Ashdale Library opens at Gerrard Street East and Ashdale
1925 to 1945
Ulster Stadium, south of Gerrard Street, north of Dundas, between Billings and Woodfield, is the site of soccer games (including a visit by the Glasgow Rangers). The stadium is the home of the Toronto Ulster United soccer team, one of the top soccer teams in Canada. It’s also the site of lacrosse games such as a 1928 game between the Canadian national team (on its way to the Olympics) vs. Toronto all-stars, attended by 5,000 fans. After World War II the stadium is sold for housing development.
Morley Avenue is now known as Woodfield Road. Kerr Road is developed on the former Ashbridge brick yard.
1930s – 1940s
CCF hall at former Woodbine Palace Theatre, 1383 Queen Street, is the scene of political and community meetings, reflecting the neighbourhood’s working class perspectives. (Until approx. 2014 the Stop’n’Go store occupied the first floor. The upstairs continues as apartments).
Ulster Stadium is closed and its land becomes a residential area – north of Applegrove Avenue (now Dundas Street) and south of Richard Street, east of Billings and west of Woodfield Road.
Roads are expanded in the area. Dundas Street is made a through street east from Hastings past Greenwood to Kingston Road. Formerly there was no east-west road along the south side of Greenwood Park. Dundas follows the former Applegrove Avenue from Greenwood to Coxwell, and the former Ashbridge Avenue from Coxwell to Kingston Road. Coxwell Avenue, which had its southern end at Eastern Avenue, is extended south to Lakeshore Boulevard. Lakeshore Boulevard is extended east, past the south end of Greenwood Raceway (originally Woodbine Raceway) to link with Woodbine Avenue. Metro Toronto plans an expressway in a route just to the east of Coxwell Avenue to become a link to the Scarborough Expressway – this was never built.
Highfield Road houses are built on what was called “the hill” south of Dundas Street – part of the former Ashbridge brick yard in the area north of Duke of Connaught School.
Mayor unveils historic plaque on Ashbridge Estate. Elm trees on the Ashbridge Estate are featured in news reports – attempts to save 175-year-old elms from Dutch elm disease, which is destroying thousands of elm trees in Ontario.
Duke of Connaught School opens a new wing to house the “baby boomers” – with a gym, swimming pool, music room, workshop, etc. Initially part of Duke of Connaught School, it is renamed Woodfield Senior School in 1965, then returned to being part of Duke of Connaught in 1989.
Duke of Connaught School’s 50th birthday celebration.
Greenwood bus route starts. It connects with the new Danforth subway line at the new Greenwood Station. Coxwell bus route connects to the new Coxwell Station. The Coxwell streetcar line goes out of service.
Ashbridge family donates its remaining “estate” and land to the Ontario government (Ontario Heritage Foundation, now the Ontario Heritage Trust) in return for not having to pay taxes for the rest of their years. Dorothy Bullen (nee Ashbridge) dies 1997, Betty Ashbridge dies 2002).
1970s and 1980s
Little India develops on Gerrard Street East, including the Naaz Theatre showing Bollywood films.
Police 55 Division opens at Dundas and Coxwell.
Ashbridge’s Bay Park opens on “new” land extended out into Lake Ontario.
Applegrove Community Complex opens in Duke of Connaught School, serving neighbourhood children, families, people of all ages. Named after its location – the Ashbridge’s apple orchard.
Duke of Connaught School’s 75th birthday celebration.
S.H. Armstrong Community Recreation Centre has extensive renovations and is officially re-opened.
Dorothy (Ashbridge) Bullen dies. A short street just north of Queen and Kent is named Dorothy Bullen Place in her honour. Dorothy and her sister Betty were the last Ashbridge family members to live in the house at 1444 Queen Street East.
Ashbridge history is featured at Market Gallery exhibit (St. Lawrence Market) in “Down by the Bay: the story of the Ashbridge family.” To coincide with this exhibit, an Ashbridge family reunion takes place at the estate at 1444 Queen East. Ashbridge’s Bay Water Festival at Queen and Coxwell includes guest speaker Margaret Trudeau. Ashbridge’s business strip is featured on maps, posters and on the etc. News website and community newspaper (operated by the Brackett family which revived the names of Leslieville and Ashbridge’s for the Queen East business districts).
Betty Ashbridge dies. She and her sister Dorothy were the last Ashbridge family members to live at the 1854/1899 house at 1444 Queen Street East.
Canada Blooms becomes tenant of Ashbridge Estate house. Later (and contnuing to today) Ashbridge house becomes home of Ontario Archaeological Society, Ontario Society of Artists.
Roden School celebrates 100th birthday.
Bike lanes open on Greenwood Avenue.
Ashbridge Commons townhouses open across from Ashbridge Estate, on former site of Stephenson’s Rent-All (and before that a gas station). The new development is marketed this way: “Ashbridge Commons is a collection of Brand New Urban Towns coming to Queen St. East in the West Beach!”
Ashbridge’s Bay Skatepark opens at Coxwell and Lakeshore.
November 30, 2011
Duke of Connaught students don top hats and tails to re-create the Duke’s sod-turning ceremony of exactly 100 years ago.
November 23, 2013
New Greenwood Park covered rink and skating path open.