Toronto’s Urban Cool

Canada’s largest city goes from bland to bold

The drake hotel is a nexus of culture in Queen West. In its café, books create a cozy backdrop for afternoon cocktails.

I hear the crowd before I see it, gleeful squeals punctuating the early autumn evening. Such is the sound track of Toronto during TIFF, the Toronto International Film Festival, where celebrity sightings and red-carpet mobs come to seem normal for ten days every September. Though I’m on my way home for dinner, I’m compelled to bike toward the roar outside Roy Thomson Hall, the sloping glass theater on the edge of the financial district in Toronto’s downtown. There, hundreds of arms wave like a field of flowers, cell-phones aloft. From the very back of the tumult, I crane my neck and catch glimpses of camera crews and a blur of well-dressed bodies. Nearby, an older woman sits on a bench with a little white dog. “What’s going on?” I ask. “Brad Pitt,” she says. “You’re not going to try to get closer?” “Nah,” she says. “There’ll be someone else tomorrow night. I’m just walking my dog.”

Her unfazed attitude seems as typically Toronto as the giddy crowd: The city is getting used to  being at the center of things. Toronto and TIFF have practically grown up side by side. A modest art house affair 20 years ago, TIFF is now the world’s largest-and some say, most influential-public film festival. In the same period, Canada’s biggest city, on the northwestern shores of Lake Ontario, has gone from being known as ‘Toronto the Good’-a euphemism for dull-to being a wildly cosmopolitan city. Nearly half of Toronto’s citizens were born outside Canada. As Lisa Ray, an actress of Indian-Polish descent raised in Toronto, tells me: “We’re the most successful social experiment in the world.”

Even urban planning guru Richard Florida agrees. In 2007, Florida, who grew up near Newark, New Jersey, left Carnegie Mellon in Pittsburg to become a professor at the Rotman School of Management at the University of Toronto. His best-selling 2002 book, The Rise of the Creative Class, heralds successful cities as those that attract and keep a creative citizenry who trade in innovation and ideas rather than old smokestack industry. Toronto is a perfect manifestation of his “Three T’s” index of good city building: technology, tolerance, and talent.

I’m curious to see how the Three T’s of Toronto play out on the streets, so I invite five local ‘creative class’ guides to show me the neighborhoods they love. Toronto is known as a city of neighborhoods, and one of these pockets is new, one is very old (well, old for a town that wasn’t incorporated until 1834), and all are vibrant reflections of a self-assured city that’s finally come into its own.