The Bennington Heights neighbourhood is situated on a flat plain of land, on the crest of an escarpment which thousands of years ago had been part of the shoreline of ancient Lake Iroquois - the forerunner to Lake Ontario.
This area was first settled in the 1870's by John Cudmore and Daniel Ryan, who operated successful market gardens on their respective properties. The Cudmore farm was subdivided for residential development in 1889 and later re-subdivided in 1912. Daniel Ryan's property, which was located just to the north of the Cudmore farm was subdivided in stages between 1891 and 1946.
The first resident of the present day neighbourhood was Thomas Weatherhead, a solicitor for the East York School Board. In 1925, when Weatherhead purchased number thirty Rosemount Avenue he had the Rosemount street name changed to Bennington, which was his wife's maiden name.
The Bennington name was also adopted by the Bennington Heights School when it opened in 1950. This neighbourhood has been referred to as Bennington Heights ever since.
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