The buzzy thoroughfare in Montreal's Verdun neighbourhood, which is pedestrian-only in summer, tops the list thanks to its sandy urban beach, "killer cocktail bars" and "stellar brunch spots".
Gertrude Street in Melbourne, Australia is second on the list, which was compiled following a survey of 20,000 city dwellers living all over the world.
The final rankings were chosen by Time Out editors after factoring in each street's food, drink, fun, art, culture, nightlife and community vibes. It almost goes without saying that the full list – which features 33 streets from Tokyo to Cape Town – is filled with inspo for places to work remotely from.
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Gertrude Street, a "beautiful" and "unassuming" thoroughfare in Melbourne's Fitzroy district, is praised for adding "a wealth of independent retail, drinking and dining joints to its cultural portfolio" instead of becoming gentrified like other parts of the city.
Great Western Road in Glasgow finishes third on the list, making it the UK's coolest street. This busy route into Glasgow is almost 18 miles long, but Time Out cites "the top bit between St George’s Cross and the Botanic Gardens" as the place to go for vintage clothes, breakfast burritos and super-cool music venues.
Deptford High Street in Southeast London places 17th on the list thanks to its array of "independent shops, cafés, bars and restaurants". These include Little Nan's, a haven of old-school British kitsch, but some of London's best rooftop bars are only a short walk away.
"It's constantly in flux," says Time Out's Chris Waywell of Deptford High Street. "Its history isn't dead and preserved: it’s the most alive street in London."
The third and final UK street on the list is Manchester's Cutting Room Square. Located in the vibrant Ancoats neighbourhood, it's hailed for its open air bars, restaurants and nightlife venues including Hallé St Peter’s, a former church hall that's now a concert space.
"If there’s one place that brings together Manchester’s proud industrial heritage with all of the advantages of a forward-looking city, it’s Cutting Room Square," says Time Out's Rob Martin.