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Travel and Leisure has a lovely photo-heavy article by Stephen Metcalfe looking at Toronto's complexities.

Before I spent time in Toronto, I had lazily classed it in my mind with Seattle and Portland—laid-back metropolises populated by well-adjusted knowledge workers. And it’s true that Toronto is nothing if not well-adjusted. Cops here are more likely to have bikes than weapons; cars slow down for a yellow rather than gunning it; passersby say “excuse me,” often for no discernible reason.

But Toronto is also the biggest city in the country. It is not to Canada as Seattle or Portland is to the U.S. “You could drop a small nuke in Trinity Bellwoods Park, and the entire cultural class of Canada would be wiped out,” Stephen Fowler quipped. Fowler, a preternaturally young-looking 51-year-old, moved from San Francisco to Toronto with his Canadian wife a dozen years ago, then watched in despair as everything that he is—a twirlymustache- sporting, vintagestore- rummaging, vinyllistening kind of guy—became a hipster cliché. He runs the Monkey’s Paw, an antiquarian bookstore in Little Portugal that is filled with lost curios and oddments of the Englishspeaking world. Spread across the tables of his little storefront on Dundas Street West are titles like Werewolves in Western Culture and A Guide to Gravestones and Gravestone Rubbing. Fowler is one of the more acute observers of civic manners I’ve met. He sees Toronto’s dilemma this way: From the Canadian perspective, it is the striver city the rest of the country resents. But from a global perspective, it remains a provincial city where the brightest lights leave for London or Dubai. “Or worse,” he adds, “for New York. Beneath all the decency and modesty is a chip on the shoulder so huge it took me years to understand it.”

Toronto’s divided self has always found expression in its urban design. In a sense, there are two Torontos: the highly planned, highly developed city known as “downtown,” a word locals sometimes say with an air of exasperation, and the city of “the neighborhoods,” enclaves of civic spontaneity like Little Portugal, where Hoofland is located. The seminal urban theorist Jane Jacobs commented on just this aspect of the city when she moved here in 1968 from her beloved Greenwich Village. “Toronto is a very refreshing city to come to from the States,” Jacobs said on a Canadian TV program. “It’s all full of romanticism and quirks and surprises and ingenuity, particularly in the way outdoor space is used.” But Jacobs also recognized Toronto’s “civic schizophrenia,” as she put it. On the one hand, it was a bottom-up, fun, free-spirited city of creatively repurposed public spaces. On the other, it was a top-down, pompous, overplanned city that seemed perversely devoted to stamping out its more creative twin.

As of 2015, the situation has grown more curious. For most of the past decade, Toronto has been a skyline of cranes, each hoisting a fresh glass-skinned tower up from a podium slab. The boom is partly thanks to Canada’s strict lending standards, which allowed it to largely avert the global real estate bubble. And so, ironically, it was the country’s infamous prudence that helped unleash the current wave of construction and speculation. Developers completed more than 20,000 new condo units across the greater Toronto area last year, an all-time record. And yet, though international money pours in, it is not the case that pompous Toronto is swallowing indieartsy- Etsy Toronto whole. The two now encroach upon one another in novel and disorienting ways. For downtown, that means borrowing from the cachet of the arts scene, sometimes to sell real estate that is unremarkable. For the art and culture scene, it means courting international recognition and money. The key term for both is design.
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