The Hippest Streets In Toronto

7 streets to explore

The hippest streets in Toronto boast boutique businesses, urban innovations, exciting menus, craft care, and overall irresistible identities. They’re the lifestyle arteries of the city, shaping the very neighbourhoods around them. These are the hippest streets in Toronto.
 

Carlaw Avenue

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It hasn’t taken long for the gentrification of Leslieville’s condo boom to touch the area’s industrial engines, and since the exodus of the Wrigley gum factory, the street’s reputation for factory conversion lofts has grown, supplying plenty of foot traffic to the independent coffee houses, pastry shops and modern fashion storefronts now occupying old warehouse spaces.
 

Roncesvalles Avenue


Today Roncesvalles is a young breeder’s paradise known for its stroller-cluttered sidewalks, dotted with a new generation of restaurants, Canadian streetwear shops, indie coffee houses, and curiosity-filled general stores like Scout and the community-minded Likely General. Its Polish roots still poke through with butchers, bakeries, and music shops catering to tradition, but it’s not the neighbourhood it used to be. Chalk the new look up to rising rent and a major street overhaul that ripped up the road – streetcar tracks and all – and choked off business in 2011.
 

Dundas Street West


Dundas Street West is a long and winding street that makes some unexpected zig zags across the city’s west end, but out in the Junction, it’s a defined thoroughfare – the centre of the neighbourhood’s business, and a forward thinking one at that: think raw food restaurants, organic grocers, and mom and pop coffee shops, amidst a range of well-kept secret bars and a number of shops for used and new books and records. There’s a reason some called it the next West Queen West.
 

Ossington Avenue

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When Vogue and the New York Times heaped praise on Queen West’s hipster appeal, they wisely highlighted the adjacent Ossington stretch, where traffic gets a little slower and the scene more concentrated in its casual indulgence. Amidst mechanic garages bike shops and tattoo parlours, here, coffee shops roll up their front windows for a view of the brewpub patio across the street while hipsters duck into low key locals, concept fashion businesses, and vintage shops.
 

Gerrard Street East

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Still home to many shuttered storefronts, Toronto is still unlocking the potential of an arguably underserviced Gerrard Street East. With locals painting entire stretches of business areas in pastel rainbows, it’s currently experiencing a wave of revitalization that’s replacing those lonely spaces with friendlier digs like snack bars, cafes with communal tables, and even theatre outfitters.
 

Queen Street West

In 2014, Vogue named West Queen West the world’s second-coolest district in the world and the New York Times called it a neighbourhood “like no other.” While Vogue praised the art-forward experiences of boutique hotels like the Drake and the Gladstone and “indie patisseries, homegrown labels, and hidden-from-view galleries,” NYT hailed its vintage shops and niche enterprises like the BYOB Cocktail Emporium. As is Queen West’s wont, some of the businesses written up have since departed, but, a heavily trafficked area that hardly sleeps, the strip endures as a vital part of Toronto’s downtown culture.
 

Geary Avenue

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Geary never became “the next Ossington” the local press pegged it as. With its plentiful rehearsal studios and alternative event spaces, for about a year, industrial Geary Avenue was hailed as a hub for local musicians. But after hype hit mainstream press, zoning hawks swooped in and served DIY venues like Geary Lane and SHIBGB’s, it hasn’t been the same since. Its hours of operation under public scrutiny, it’s with little surprise that current occupants keep more regular business hours, so today the independent businesses you’ll find more production-oriented enterprises like microbreweries and distilleries (Blood Brothers Brewing and Yongehurst Distillery), between the studios and auto body shops.
 

Image courtesy Muttonheadstore via Instagram