Montgomery Road

Take a slow evening walk down Montgomery Road and travel back through layers of Toronto history with every step. This quiet stretch was originally cut through private farmland by Thomas Montgomery himself to give local farmers a faster route to the Humber Mills — and well into the 1940s it was still mostly open field. It's a contemplative, low-key outing perfect for unwinding while soaking up the city's lesser-known past. Perfect for after work — drop in solo or bring a friend. No experience necessary.