Much of the land west of Roncesvalles was once part of Sunnyside Farm, owned by John Howard, Toronto’s first surveyor and one of Canada’s greatest architects. In 1873, Howard donated a large chunk of land to the City of Toronto. In 1890, he also donated his beloved Colborne Lodge and the surrounding land. These great gifts formed most of what is today High Park, the largest in Toronto.
Colonel Walter O’Hara owned most of the land on the east, living on a large estate he named West Lodge. He named Roncesvalles after the gorge where he fought during the Battle of the Pyrenees in 1813. Many other neighbourhood streets have an O’Hara connection, such as Marion (named for his wife), and Constance (named for his daughter). Fermanagh is the county of his birth in Ireland. The Colonel died in 1874.
Residential homes began to appear from the early 1900s on, as Toronto experienced a massive building boom. For the first half of the 20th century, Roncesvalles residents were mostly of British origin. In the post WWII years, a large number of Polish immigrants settled in the area, setting up churches, banks and businesses which remain important local institutions. Every year, Roncesvalles celebrates the Polish contribution to Toronto’s cultural mosaic with the Roncesvalles Polish Festival.