Sir Winston was founded in 1959, and named after the former British Prime Minister, known mainly for his leadership of the United Kingdom during World War II.
Its campus features an all-weather, artificial turf, football/soccer/lacrosse field(to be completed in August 2017), an all-weather track, a parking lot, and a two-story building. The building includes a gymnasium with multiple changing rooms for boys and girls as well as showers, a weight room, and an auditorium. A brand new, two-level, cafeteria was completed in 2013. The old cafeteria has been converted into a larger library, while the old library has been converted into two classrooms. SWC is a barrier-free facility, courtesy of elevator access to all levels. The school's colours are navy blue and gold, and its mascot is the Bulldog.
The school runs two Specialist High Skills Major programs, one in Information and Communications Technology and the other in Arts and Culture. The school recently opened a new broadcast studio on the main floor, outfitted with studio lighting and high definition video cameras, that is used to broadcast the morning announcements - a student-run program called SWC NEWS. SWC is one of two secondary schools in St. Catharines offering French Immersion programming.
Renovations over the summer of 2013 gave the school 6 new science labs and 4 new computer labs.
The school is also built on the same plans as another school in the city, Laura Secord Secondary School, located only 6.3 km away.