The Hillside community has a long and proud farming tradition. The spiritual centre of this rural hamlet was the Hillside Church built in 1877 at Finch Avenue and Reesor Road. This historic church is still standing at 361 Old Finch Avenue. The Hillside Schoolhouse, built in 1872, is located on Meadowvale Road where it now serves as an outdoor education centre for the City of Toronto.

Many of the old Hillside farms were expropriated in 1972 by the provincial government for the building of the proposed Pickering Airport which was never developed. In 1995 both the government and privately owned Hillside properties were incorporated into the "Rouge Park" conservation area.