Map: Kensington Market

Kensington Market, once dubbed "The Jewish Market," was founded in the early 1900s by Eastern European Jewish immigrants. The tight knot of downtown streets was once cramped with bakers, tailors, and furriers; the neighborhood has graduated from the city’s premier bohemian enclave. Queen Street West has enjoyed a more recent renaissance, graduating from sad-sack, booze can-littered drag to Toronto’s hippest area.

Begin at Augusta and College Street, walking south down (1) Augusta, the city’s ultimate bohemian-chic address, lined with organic bakeries (try the shortbread cookies at Alchemy), Mexican bodegas (El Trompo), tapas restaurants (Torito), and pupusa-slinging Latin American grocery stores. The peckish should fortify with an empanada at Chilean stalwart lunch spot (2) Jumbo Empanadas (245 Augusta Avenue), where the titular homemade pillows are toothsome, piping hot, and perfectly oven-gilded. Continue southward for a killer latte (potent and smooth) at iconic family-owned (3) Casa Acoreana (235 Augusta Avenue), more caffeine shack than café. Turn left at Oxford Street to enjoy the colorful outdoor carnival of fruit-and-vegetable stands and exotic cheese shops, then take a right at Kensington Avenue, past rows of vintage clothing shops. (4) Courage My Love (14 Kensington Avenue) is the time-honored Kensington classic.

Double back toward Baldwin, then hang a right toward Spadina Avenue, and walk south toward Dundas Street, where you’ll find yourself in the bowels of (5) Chinatown. Toronto claims five different Chinatowns. This downtown version is the largest; a chaos of Chinese restaurants, grocery stores, exotic fruit stands (find anything from dragonfruit and kumquats to mangosteens), noodle and bubble tea bars, and useless trinket and souvenir shops cramp broad sidewalks—always crowded with pedestrians in a terrific hurry.

Hang a right on Queen Street, and walk toward Bathurst Street, where so-called (6) Queen West West officially begins. Continue wandering westward past Palmerston Street: This forever-flourishing drag has graduated from the grimy and unsavory to the city’s hippest strip: find artful one-off clothing boutiques (Kami Kaze, Girl Friday, Pho Pa), cafés, tea rooms (Red Tea Box), home décor emporia, and fine Japanese stationers (The Paper Place). Stay the course until (7) Trinity Bellwoods Park (790 Queen Street W); grab an espresso and a croissant at French patisserie Clafouti and duck in for a browse at booklovers’ bookshop Type. Enjoy your caloric spoils in the park—one of the loveliest and most bustling urban green pieces in town. Continue westward past Shaw Street, and pop into (8) The Museum of Contemporary Canadian Art (MOCCA) (952 Queen Street W; www.mocca.ca), then into (9) The Steven Bulger Gallery (www.bulgergallery.com) down the way at 1026 Queen Street W. Owner Stephen Bulger is one of the only dealers in the world to represent leading photographer André Kertész. Continue past a slew of independent art galleries and witness the slow gentrification of a once ramshackle neighborhood. Push forth until your last stop, a cocktail at (10) The Drake Hotel (1150 Queen Street W, www.thedrakehotel.ca), at Beaconsfield Avenue.

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