Kensington Market is four blocks of Victorian rowhouses converted to produce stalls, vintage shops, and patios — all of which push awnings and umbrellas to the curb line. Augusta and Baldwin hold near-continuous cover through the summer, and the narrow lane geometry keeps building shadow on one sidewalk at all times.
These picks pair the Market with Chinatown’s Spadina awnings and the University of Toronto’s elm quads. Pedestrian Sundays close Augusta to cars entirely — the best version of this walk.