“In 1800, James Kennedy came from Schenectady, New York and settled in the ‘far northern woods’ of the Township just east of the road which bears his name today.” - A history of Scarborough, Robert R. Bonis, Published by Scarborough Public Library, 1965.)
According to this book, the Scarborough census of March 1809 showed only 34 men, 24 women and 82 children less than 16 years of age living in this Township. In 1819 the number was 349 people in total, and thus James Kennedy was among the first pioneers of Scarborough.
James Kennedy is listed as one of the elders behind the building of the first church in Scarborough, St. Andrews Presbyterian, in 1819.
Much of the land owned by the Kennedys appears to have been between Scarborough and Markham.

Source W. David Perkins.