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.
David Gibson, a distinguished land surveyor, was another leader in this community. Like most of his neighbours, Gibson participated in the ill-fated Toronto Rebellion of 1837. He was thus charged with high treason and escaped to the United States were he found employment as the First Assistant Engineer on the building of the Erie Canal.
Gibson returned to his Yonge Street farm in 1851, after being pardoned for his role in the Rebellion. He then helped to establish the "Willow Dale" post office, named after the many willow trees that once graced this district. Members of the Gibson family were still living in Gibson House in the 1920's when the residential subdivision of Willowdale began to take place. The Gibson House, circa 1851, is still standing in its original location at 5172 Yonge Street and is now a historic museum.
Willowdale is a vibrant and cosmopolitan urban centre filled with luxury condominiums, custom built homes, shining office towers, a newly renovated shopping mall and theatre complex, an ultra modern civic centre, a world-class aquatic centre and a highly acclaimed Centre for the Performing Arts which hosts local and world class entertainment.
Willowdale is also the home of the newly rebuilt Earl Haig Secondary School which has an outstanding academic reputation. Earl Haig is also highly regarded for its Claude Watson Arts program where students can major in either dance, drama, music or visual arts.