The Bridle Path of present day could hardly have been envisioned by Alexander Milne, who originally settled on what is now Edwards Gardens in 1827. Milne operated woollen and saw mills on the banks of Wilket Creek until 1832, when a dwindling water supply forced Milne to move east to a mill site along the Don River. The Bridle Path inconspicuously spent the rest of the 1800's and early 1900's as farmland. It wasn't until 1929, when the Bayview Bridge was built over the steep Don River Valley, that the area was considered for residential development.

Hubert Daniel Bull Page, a Toronto-based land developer, was one of the founders of the present day neighbourhood. Page envisioned the Bridle Path as an exclusive enclave of estate homes. and in 1929, Page built the Cape Cod Colonial style house at number 2 The Bridle Path, in an effort to spark interest in his subdivision. Early plans for this neighbourhood called for an elaborate system of equestrian Bridle Paths. These Bridle Paths have long since been paved over, however their legacy remains in the Bridle Path's unusually wide streets and in the name of this neighbourhood.