Originally called Kummer's Settlement, Willowdale was first settled in 1797 by American Jacob Cummer.

A mill and tinsmith shop owner, self trained doctor and veterinarian, Cummer was held in high regard by his community; hence the naming of the community.

Willowdale was originally settled by Jacob Cummer, who immigrated to Canada from the United States in 1797. Cummer was a mill owner on the nearby Don River, a proprietor of a tinsmith shop on Yonge Street and a self trained doctor and veterinarian. Cummer was held in such high esteem by his neighbours that this area was originally known as Kummer's Settlement.

In the 19th century, David Gibson settled in the community as a land surveyor helping establish the community however feld to the United States following his participation in the Toronto Rebellion of 1837. Upon his return Gibson helped construct the Willow Dale post office named for the many willow trees that were once part of the region.

By the 1920s residential subdivision evetually become part of the Township of North York and then the City of Toronto.