Don Jail

Seek out the striking Italianate façade of the Don Jail, a building that looms large in Toronto's architectural and social history since opening in 1864 as the largest jail on the continent. Designed by William Thomas — the same architect behind St. Lawrence Hall — the exterior is genuinely impressive, full of dramatic stonework and grand ambition that feels almost at odds with its grim purpose. It's the kind of landmark that rewards a closer look and sparks a great conversation on the walk home. Perfect for after work — drop in solo or bring a friend. No experience necessary.