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Bennington Heights The Streets of Leaside

Cudmore Farm

Cudmore Farm

While not technically in Leaside, Bennington Heights Drive is close enough to share an M4G postal code. This curving road is the “main street” of the neighbourhood known as Bennington Heights.

Thousands of years ago, Bennington Heights was on the shoreline of Lake Iroquois (Lake Ontario). It 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. The Cudmore farm was subdivided for residential development (a trend that lives on today!) 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.

In 1912, Ryan sold his property to Thomas Weatherhead, a solicitor for the East York School Board. When Thomas lived at 30 Rosemount Avenue, he had the street’s name changed to Bennington Heights Drive, Bennington having been his wife Evelyn’s maiden name.

Evelyn Maude Bennington was the daughter of Colonel Alfred Bennington (1860-1933) and Gertrude Peck of Prescott, Ontario. On August 31, 1925, she married Thomas Weatherhead of Toronto. Thomas was a successful lawyer, practising with his sons David and Peter until he died on December 24, 1975. 

Evelyn Weatherhead was successful in her own right, serving as national president of the Home and School Association of Canada. In 1951, she was president of the Ryerson Institute (now University) and on April 8, 1958, was elected the president of the Ontario Home and School Association. The Weatherhead family were members of Rosedale United Church, and both of their funeral services were held there. Evelyn died on June 26, 1969 and is buried beside her husband in Mount Pleasant Cemetery.

Jeanne Hopkins spent most of her life in the historic Henry Farm community of North York. She realized her passion for local history in the Canadiana department of the North York Public Library, where she worked for 27 years. She is the author of many articles and five books of local history.