Archeological surveys have shown that the land south of what is now Cootes Paradise was inhabited by successive aboriginal nations. In the early seventeenth-century, when the first French explorers and missionaries visited the western edge of Lake Ontario, they found the region populated by native people, who were referred to as the Neutral Nation because of their neutrality in the disputes between the Iroquois Confederacy and the Huron.

In the mid-seventeenth century, the Neutral Nation and the Hurons were defeated by the Iroquois Confederacy. Eventually, Ojibway from what is now northern Ontario began to push southwards and displace the Iroquois and occupied the land until they themselves were displaced by European pioneers.

Following the creation of Upper Canada in 1791, the land upon which Westdale is now located was surveyed as part of the Township of Barton. Shortly afterward, the boundary was adjusted and the lots west of present-day Paradise Road were incorporated into the Township of Ancaster. This area of the township situated below the escarpment was commonly referred to as the Gore of Ancaster.

Following the transfer of the land from the Township of Barton to the Township of Ancaster, the land upon which Westdale is now located became lots 57 through 60 of Concession 1.

Early settlers of these lots include the Forsyths, Ashbaughs, Clines, Paisleys, Buttrums, Brambergers and Strouds. Land use was primarily devoted to agriculture.