Leaside ❤ Bennington

Alan Redway

Our former premier Mike Harris now lives in Bennington Heights. When I met him recently Mike said, “Nobody cares about Bennington Heights.” Well Mike, that’s hard to believe, but I can tell you, we sure looked after it before amalgamation.

Most people assume that Bennington was always part of the former Town of Leaside, but it wasn’t. Both the Bennington and the Governor’s Bridge communities were actually part of the former Township of East York prior to its merger with Leaside in 1967, when we all became the Borough of East York.

Both before and after East York was incorporated Bennington, known originally as Rosemount, was composed of orchards and market gardens. In 1925 a young lawyer, Thomas Weatherhead, built a home in the area for himself and his new bride Evelyn Bennington. 

Thomas went on to become an East York school trustee and later the school board’s solicitor. It was Thomas Weatherhead who persuaded East York township council to change the name of his street to Bennington Heights Dr. in honour of his wife.

During the 1950s Evelyn Bennington Weatherhead served as the national president of the Home and School Association of Canada. It was also Thomas Weatherhead who chose the site for Bennington Heights School at the end of Bennington Heights Dr.

For a time the area was known as the Moore Park Annex, but since both the school and the longest street were named Bennington Heights, the local real estate agents began to refer to the whole area as Bennington Heights.

Before Bennington Heights  school was opened the growing numbers of children living in the area had to be bussed to Whitney school in Toronto because Leaside refused to have them.

Thomas and Evelyn’s three boys, David, Peter and Gerald went to high school at North Toronto Collegiate while their sister Barbara went to Oakwood Collegiate.  Before Leaside High was built many Leaside students attended Jarvis Collegiate. David and Peter later practised law with their father.

When I was a kid, Pogue’s Riding Stable was located in Bennington Heights on the south-west corner of Bayview and Moore. I still can visualize a horse and cutter from Pogue’s making its way along Bessborough Dr. in the winter on the snow-covered road before the days of snow plows and salt.

Many well- known people have lived in Bennington Heights over the years, including the author  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; Bruce Brown, the architect for many Leaside churches;  and  David Weatherhead, who served as a Liberal Member of Parliament for Scarborough West.

In 1966 the residents of Bennington Heights and Leaside banded together to successfully defeat a proposed high rise development on Mallory Cres.

We’ve been together ever since and we care.

About Alan Redway 30 Articles
Alan Redway is a retired lawyer, born in Toronto, with a degree in Commerce and Finance from the University of Toronto and a law degree from Osgoode Hall law School. Mr. Redway served for ten years on the council of the Borough of East York, six of those years as the Mayor of East York and a member of Metropolitan Toronto Council and Executive Committee. Later he was elected to the parliament of Canada where he served for almost ten years as a Progressive Conservative member of the House of Commons and as Minister of State (Housing). He has written for Leaside Life and the East York Chronicle. In 2014 he published his first book, "Governing Toronto: Bringing back the city that worked."