From tomatoes to townhouses: Jane’s Walk heads to Bennington Heights
Bennington Heights, a triangular-shaped midtown residential neighbourhood, is bounded by Mount Pleasant Cemetery to the north, the Don Valley ravines to the west (Mud Creek) and east (Cudmore Creek), and is situated on the cusp of the ancient Lake Iroquois.
Bennington Heights has the ambience of a mid-20th century residential neighbourhood, an enclave like a more modern Wychwood Park, with its layout including winding roads and cul-de-sacs: connecting streets – Evergreen Gardens, Heath Street East; circular roads around common space – Heathbridge Park, Orchard Green and cul de sacs – Heathbridge, Windmill, Garden Circle.
The residential area, Rosemount, now called Bennington Heights, was first settled in the 1870s by John Cudmore and Daniel Ryan, who operated successful market gardens on their properties until the area was developed in 1889. Their tomatoes were some of the best in Toronto, and they sold exclusively to the Queen’s Hotel, Toronto’s finest hostelry located where the Royal York Hotel now stands. The Cudmore farm was subdivided for residential development in 1889 and again in 1912. Ryan’s property, located just north of the Cudmore farm, was also subdivided in stages, first in 1891 and again in 1946.
The development of Heathbridge Park, the northern and central parts of Bennington Heights, was influenced by its early establishment as a Co-operative Residential Community (CRC), designed by well-known architect James A. Murray and his students in 1946.
Recently, Bennington Heights has faced the challenges of intensification common in many Toronto neighbourhoods:
- -Replacement of original housing,
- -Townhouse development on Bayview Heights Drive.
Despite being located south of, and adjacent to the Town of Leaside, incorporated in 1913, Bennington was part of the Township of East York from 1925 until Leaside and East York united in 1967 to form the Borough of East York. This created some awkward situations; for example, at one time the schoolkids were not able to attend Leaside schools, instead they had to attend North Toronto Collegiate for high school. Today, however, Bennington shares a postal code (M4G) with Leaside.
Bennington Heights has also been the home of some notable people including:
- -Margaret Atwood, who grew up there and has written books about her neighbours;
- -Norman McLeod, the first and long-time principal of Leaside High School;
- -Manley MacDonald, the Ontario landscape artist who painted many Bennington scenes in the 1930s;
- -Lotta Dempsey, a Toronto Star columnist;
- -Frank Tumpane, a Toronto Telegram columnist;
- -Mike Harris, the former Premier of Ontario;
- -Bill Morneau, the former federal Minister of Finance; and
- -Walter Windeyer, champion yachtsman, first non-European to win the Gold Cup.
We will do a triangular walk through the Heights – (see map above):
Gathering (and end) point: Evergreen Gardens Park, southwest corner of Moore and Bayview Avenues:
- -west on Evergreen Gardens
- -southeast on Lumley Avenue, Heath Street and Bennington Heights Drive (and depending on time – Moorehill Drive)
- -the Lake Iroquois shoreline
- -north on Bayview Heights Drive
- -returning to Evergreen Gardens Park
1. 1 Orchard Green
The renovated house that architect James A. Murray designed for Murray Ross, the founding president of York University and was written up by Dave Leblanc, the Architourist, in the Globe and Mail in 2019,
2. 3 Garden Circle
- -Garden Circle – site of Margaret Atwood’s childhood home,
- -Garden Circle – renovated home by Heather Dubbeldam.
3. 411 Heath St. East
Designed by prominent architect Hugh Lachlan Allward (of Allward and Gouinlock) for Ivan M. Capon in 1929. In 1998, a real estate article described it as “rambling, two storey, faux Tudor mansion owned by Thomas George Bata, son of Thomas and Sonja Bata, shoe magnates and philanthropists.” The real estate agent described the home as “a true jewel in the centre of Toronto – nothing like it…includes a coach house, separate nanny quarters, three fireplaces, in-ground swimming pool and pool house.”
4. 30 Bennington Heights Dr.
The house dates from 1925 and is likely the oldest original house in situ. It retains its original design and was sold recently (January 2025). In 1912, Thomas Weatherhead, a solicitor for the East York School Board, purchased the property from Daniel Ryan. On August 31, 1925, he married Evelyn Maude Bennington. The home’s address was 30 Rosemount Ave., but he had the town of East York change the street’s name to Bennington Heights Drive, as a wedding gift to reflect Evelyn’s maiden name. Eventually Bennington would become the name of the community. Both 411 Heath St. East and 30 Bennington Heights Dr. overlook Mud Creek.
5. Lake Iroquois Lookout
This public space at the south end of the expansive grounds of Bennington Heights Elementary School looks out directly (southwest) across the CP rail line to the Governors Bridge neighbourhood.
6. 28-32 Evergreen Gardens
A row of six luxury townhouses that were proposed for a pair of Evergreen Gardens lots situated near Bayview and Moore became a flashpoint in a low-profile, but closely watched development application in 2017. The two properties previously housed 1950s-style bungalows that were purchased by a developer.
The case stalled at the Local Planning Appeals Tribunal (LPAT), for months, dealing with the surprisingly slippery question of what precisely constitutes the interior of an established neighbourhood.
Residents of this corner of Bennington said that the project, by a Vaughan-based numbered company, violated the ambience of a historic residential neighbourhood. The application was eventually approved with minor changes and construction is now near completion.
