The Bentway is one of Toronto’s more inspired urban reinventions: a stretch of public space carved out beneath the Gardiner Expressway, transforming what was once dead space into a cultural corridor. Spanning a little over a mile, it connects neighborhoods, people, and programming through a mix of art installations, performances, skating, walking paths, and community events—all unfolding under the concrete canopy of the highway above. It’s surprisingly calm, occasionally buzzy, and always a little unexpected. On any given visit, you might stumble upon a public art installation, catch a pop-up performance, or simply see locals lounge with coffee in hand. In summer, expect tons of outdoor programming with markets, concerts, and food trucks; in winter, the 720-foot, figure-eight skating trail steals the show.