High Park North exists on part of an old native trading trail. Most likely used by members of the Missisauga Anishinaabeg tribe. This trail is the namesake for Indian Road, Indian Road Crescent, and Indian Grove.
High Park North emerged as a neighbourhood once Bloor Street was widened and evened out following World War I, when most of the residential homes which still exist today were built.
The first building in Canada designed by a Canadian trained female architect was constructed in the neighbourhood. This landmark building by Jean Hall is a 1925 fourplex located at 63 Jerome Street in Toronto.