Boston’s oldest neighborhood has the narrowest streets and the tallest ratio of wall to sky. Three picks through the pasticceria grid where the sun barely lands.
The North End’s street plan predates the republic, and its four-story brick rows on 20-foot streets produce Manhattan-canyon shade ratios at rowhouse scale. Hanover Street is the sunny spine; everything one block off it — Salem, Prince, North Margin — sits in building shadow most of the day.
These picks run the shadow streets and touch Hanover only at the crossings. The Greenway’s pergola and the harborwalk’s wharf buildings extend the network east.
Under the Greenway pergola, then up Salem Street’s shaded slot. Open 24 hours; the walk works at any temperature.
The mall’s linden allée, then Hull Street’s brick shadow up to the burying ground’s crest breeze.
The trellis walk, then north along the harborwalk under the wharf buildings’ shadow line.
Stay Cool computes a shadow-aware route for any city we map.