The land around Keswick's Roches Point was acquired by Major General Sir Peregrine Maitland in the early 1800's with belief that he could turn it into the capitol of Upper Canada but his attempts were unsuccessful.

Keswick was originally acknowledged as Medina and was part of the Township of North Gwillimbury before becoming part of the Township of Georgina.

The range was formerly considered part of "cottage country" for those who lived in Toronto up until the late 1980s, when major development further opened up access to Keswick, expanding its population.

Close to Holland Marsh the Keswick marsh and surrounding area has been known for its rich, loamy and fertile soils.