Much of west Roncesvalles was a part of Sunnyside Farm, owned by John Howard, one of the Toronto's first surveyors and one of the country's greatest architects. In 1873, Howard donated a large piece of his land to the city. Colonel Walter O'Hara was the owner of most of the land in the East where he built a large estate name West Lodge. He named the area after a gorge where he fought during the Battle of the Pyrenees in 1813, with some of the street-names named after his family members. Roncesvalles was originally within the boundaries of Parkdale but annexation came soon enough.
For the first-half of the 20th century, area residents were mostly of British ancestry and it was around that time that residential homes began to appear during a building boom in Toronto. In the post-WWII years, Polish immigrants began settling in the area and setting up many of the local institutions that still stand today, giving Roncesvalles a European flavour that can't be found in many areas of Toronto. The homes are mostly Edwardian and Victorian examples on deep lots that sit on leafy tree-lined streets, perfect for young professional families to push a stroller along.
The annual Roncesvalles Village Polish Festival happens each fall, closing Roncesvalles Avenue to the city traffic. It has amusements including rides for the kids, craft and clothing stands, outdoor musical entertainment and food stands galore; an estimated 300,000 people attend the festival. High Park is a short walk from the neighbourhood with its many attractions and sports facilities. The many trails are used by walkers, joggers and hikers alike. The main high school in the area is Parkdale Collegiate and there are also two schools that cater to Junior and Senior classes: Fern Avenue and Parkdale Junior/Senior School.
The village feel of Roncesvalles carries over to its shopping district along Roncesvalles Avenue with its independent, family-run businesses but there are a few more well-known chains thrown in for good measure. The are is sometimes known as 'Little Poland' and it is the perfect place to enjoy tradional Polish culinary delights. Roncesvalles has a prime location in the West-End, keeping its traditions close, Toronto's very own European village within walking distance of the Western Beaches and the boardwalk