Willowdale was once a rural hamlet known as Lansing back in the 1800's and was originally settled by Jacob Cummer who immigrated from the States to Canada in 1797. He owned a mill on the nearby Don River, was a proprietor of a tinsmith's shop on Yonge Street and a self-trained doctor and veterinarian. His esteem and influence was so well-respected that the area was originally known as Kummer's Settlement. Another leader in the community, David Gibson, participated in the ill-fated Toronto Rebellion of 1837, was charged with high treason and escaped to the United States where he helped in building the Erie Canal. After being pardoned, he returned to his farm on Yonge Street and helped establish the 'Willow Dale' post office, so name after the many willows trees that graced the district. The Gibson house is now standing in its original site at 5172 Yonge Street and is now a historic museum.
Single-family homes can range in date from the early 1910 to 1950's constructions which consisted of one and two-storey pre-war houses and modest one-and-half story postwar homes. Approximately a quarter of Willowdale's brick bungalows were built 1946 and 1960, but each year, more and more of these are torn down to make way for new development. Around the end of the 1990's, large replacement two-storey luxury homes were constructed by tearing down the original. This was the first neighbourhood to get the term 'monster homes' applied to its new development. The lots are large, usually about 50 feet wide by 130 feet deep and are prime candidates to be combined to form building sites for condos or townhouses.
The North York Civic Centre is a mixed-use athletic facility that includes the Douglas Snow Aquatic Centre and the North York Central Library. Next to the centre is Mel Lastman Square, a public space complete with a large amphitheatre, wedding pavilions, a garden court and a reflecting pool which turns into a skating rink in the wintertime. Next to the square is the Ford Centre for the Performing Arts which also houses the Art Gallery of North York, the George Weston Recital Hall and the Studio Theatre. Across from the centre is the Willowdale Lawn Bowling Club. Located on Church Avenue, the Mitchell Field Community Centre has an ice arena, an indoor pool, a gymnasium and community meeting rooms.
Willowdale has a great variety of public elementary school including, Churchill, Finch, Hollywood, McKee and Yorkview. Earl Haig is a public high school, well-respected for its art programme. There are three catholic school in the area, St. Cyril, St. Edward and St. Gabriel. United Synagogue Day School is a private jewish school on Bayview Avenue. Willowdale is a neighbourhood that is on the move developing quality facilities and infrastructure for its residents and it has come a long way from its humble beginning as a rural hamlet in the 1800's.