The High Park neighbourhood contains a wealth of history. The area north of Bloor Street was formerly part of the Town of West Toronto Junction, which was annexed by the City of Toronto in 1909. The historical house at 191 High Park Avenue was built in 1888 for D.W. Clendenan, the first mayor of West Toronto Junction. 

The High Park property south of Bloor Street, was purchased in 1836 by John Howard Toronto's first surveyor. Howard named his estate High Park because of its high elevation and magnificent view of Lake Ontario. In 1873 Howard deeded his beloved High Park estate to the City of Toronto. John Howard's former residence Colborne Lodge is still situated on its original site in High Park, where it is now a public museum.

The High Park neighbourhood is home to a wide range of people. Its highly regarded schools including Humberside Collegiate attract many families with school age children to this neighbourhood.

High Park contains a diverse housing mix. Families gravitate to the single family homes in the neighbourhood. There are also a large number of rental opportunities in High Park which appeal to singles and couples. The topography of the High Park neighbourhood features gently rolling hills, winding streets, and towering Oak trees that enchant and delight all those who live here.

Launched in 1998, the Jamie Bell Adventure Playground (located at 1873 Bloor St. W. in High Park) is a family meeting place that was inspired and built by the imagination and creativity of the local community and its children. A fire at the playground on March 17 destroyed a large portion of the popular structure. This beloved neighbourhood landmark was rebuilt in 2012.