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Hippies followed in the 60s, but today the peace and love has made way for ethnic eateries, organic grocers and the kind of grungy-but-cool cafes that people with beards and flannel shirts seem to like.
The independent spirit is still strong, though: when a Nike store tried to open, the community reacted by dumping dozens of running shoes splattered with red paint in protest at the treatment Nike's workers receive around the world. Lee advises me to limber up; my stomach and I are in for an awfully big adventure.
Suggest that to John Lee, however, and you'll be met with an exaggerated eye-roll."This is Toronto," booms the Harley-riding, ridiculously cool chef, his laughter bouncing off the eatery's Formica tables.
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Appropriately, our exploration of Toronto starts at St Lawrence Market, a red brick behemoth that sprawls lazily across two city blocks.
Appropriate because this is where Toronto itself had its beginnings in 1793.
We jump in a cab for the 10-minute drive to one of Toronto's most eclectic neighbourhoods, Kensington Market; thankfully, there's no evidence of the traffic that held us up for an hour on the drive from the airport the day before ("That's because the Maple Leafs were playing," says the taxi driver, referencing the city's adored ice hockey team). Located on the upper spine of Spadina Ave, one of the longest streets in Toronto, it was here that Jewish immigrants from Eastern European arrived at the start of the 20th century.
Located in the scruffy Kensington Market district, where Downtown frays into alleyways that look as though they'd do you mischief, the nondescript restaurant with the faded signage doesn't appear to be the kind of place where tourists should linger after dark.
But where it really gets interesting is in the 19th and 20th centuries, when successive waves of immigrants from Europe and Asia chose to begin life anew in this vast, empty land." That's certainly true in Toronto, where half of the city's 2.6 million population was born outside of Canada and where a stroll down any street will throw up some of the 140 languages and dialects spoken.
As locals never tire of telling visitors, the United Nations calls Toronto the most ethnically diverse city in the world.
We start at Fika, a cafe which looks as though it was airlifted lock, stock and barrel from Scandinavia (the word Fika is, in fact, Swedish for "coffee break").
As if we needed any more confirmation of how achingly hip this cafe is, a fashion magazine photo shoot is taking place in the front room.