On a recent Saturday evening in downtown Toronto, underground superstar the Weeknd made a rare hometown appearance. The 22-year-old musician (real name: Abel Tesfaye)—known for grinding, clothing-optional hip-hop, R&B, and electronic jams—was DJ-ing a set at one of his local hangouts, a speakeasy-style cocktail lounge called Goodnight. It was too packed to dance, but that didn’t stop people from trying; the multiethnic crush of twenty- and thirtysomethings jostled roughly in time to the beat. From the unmarked alley-side entrance to the retro drinks menu (featuring such concoctions as the Monkey Gland and Satan’s Whiskers), the scene had the hallmarks of the kind of nightlife people like to later claim they’d been a part of—the sort of party that, once the hangover subsides, inspires screenplays and fashion shoots and commemorative coffee-table books. Goodnight was impossibly stylish and photogenic. It felt slightly dangerous, out of control, and loaded with possibility.
It was not the Toronto I remembered.
Safe, clean, bland: until quite recently, these were the adjectives traditionally applied to Canada’s financial and media capital. Toronto was known primarily for its livability, and for its admirably welcoming attitude toward immigrants. Yet despite a steady influx of new cultures, the city lacked verve, vitality, a sense of pride or of real identity. What Toronto was missing in character, it made up for in its rigorous pursuit of sensible liberal values. For cultural cues, Toronto looked to both New York and London, while keeping a disdainful eye on its more effortlessly hip older sibling, Montreal. It exported some of its talent to the United States, but—as is generally true of Canadian artists—those who stayed behind found that their fame stayed behind, too. (The Tragically Hip, indeed.)
Lately, however, Toronto has undergone a remarkable sea change, one that’s redefining the city as stylish, sophisticated, cosmopolitan—cool, even—yet still utterly local. Goodnight is emblematic of this new spirit, as is Matt George, the guy behind the bar, who happens to be the owner. A former snowboarder turned entrepreneur who moved to Toronto from England when he was 21, George is street-smart, business-minded, and totally committed to his adopted hometown. In addition to Goodnight—a favorite haunt of Toronto-based musicians such as Drake and Metric—he owns an upscale-casual men’s clothing store, Nomad, that features a selection of up-and-coming labels (Robert Geller; Gitman Bros. Vintage; S.N.S. Herning) and understated Canadian brands such as the easily wearable (despite the name) Wings & Horns. With footholds in fashion, music, and nightlife, George is undeniably wired into Toronto society and beyond. (At press time, he was one of only five people whom Kanye West followed on Twitter.) And his burgeoning empire—which stretches from Toronto’s increasingly polished, high-rise-filled downtown to the Queen West enclave, full of trendsetting shops, restaurants, and bars—mirrors the evolution of the city itself.
Toronto’s transformation can be traced, in part, through its changing skyline. The uninspiring, 36-year-old CN Tower, the tallest freestanding structure in North America, is no longer the city’s defining landmark. In the past decade, starchitects have been reimagining downtown Toronto: there’s Will Alsop’s Sharp Centre for Design at the Ontario College of Art & Design, a black-and-white domino held aloft by brightly colored struts that resemble pick-up sticks. There’s Daniel Libeskind’s alternately lauded and reviled Michael Lee-Chin Crystal, an addition to the Royal Ontario Museum—all steel, glass, and hard angles that sever the stately lines of an otherwise lovely building. Most successful is Frank Gehry’s expansion of the Art Gallery of Ontario, with its graceful, curvilinear glasswork melded to the exterior of the building. And at the heart of downtown—just west of the Financial District—is the monolithic TIFF Bell Lightbox, the $191 million headquarters of the Toronto International Film Festival, held each September.
Plenty of cities can lay claim to high-profile architecture. Paralleling this, however, is an insatiable boom in residential and hotel development. According to research company Emporis, Toronto has more high-rises under construction than any other city on the continent. The view from the roof of my hotel, the recently opened Thompson, recalls Shanghai or Dubai; I lost count of all the cranes. Among the current builds are the new flagship Four Seasons Hotel, opening this summer and featuring Daniel Boulud’s first restaurant in the city; and the massive Shangri-La Hotel, debuting next month with another New York restaurant import, an outpost of David Chang’s Momofuku chain. Both properties arrive hard on the heels of the Ritz-Carlton and Trump hotels that opened in February 2011 and January 2012, respectively.
The real estate market, meanwhile, has been humming along unabated by the financial crisis, a fact that can be partly attributed to immigration: greater Toronto is growing by 100,000 people each year, with the biggest percentage arriving from urban centers in South Asia and China. (It’s a good town for dumplings.) Indeed, the population is large enough to support two Chinatowns in the city center alone, one downtown and one just east. Still other neighborhoods are dominated by émigrés from Italy, Portugal, Greece, and the Philippines. When I was growing up there in the 1970’s and 80’s, multiculturalism was the ethos of Toronto’s immigration policy—in contrast to the “melting pot” drive for homogeneity embraced in the United States—and remains very much a point of local pride. The range and variety of national heritages here is never more evident than during the FIFA World Cup, when the entire city develops a raging case of fútbol fever.
What makes all this especially exciting for travelers is that while downtown Toronto grows ever denser and more international, the city’s creative classes have established stylish outposts all their own. Look at Queen West (one of the city’s thriving art and design districts, anchored along a three-mile stretch of Queen Street); at the Distillery District (a complex of shops, restaurants, and arts organizations located on the 14-acre grounds of a former whiskey distillery, on Toronto’s east side); and at Little Italy (a charming district of bars and eateries along College Street, to the north). In any of the above, you can’t get too far without running into a table crafted out of a reclaimed barn door. There’s a bountiful supply of Edison-bulb-lit restaurants emphasizing seasonal organic ingredients; stores stocking both international and homegrown designers; galleries, theaters, and music venues; and clubs and lounges you might actually want to spend an evening in. And despite the increasingly urbane and worldly vibe, the city still pays tribute to the big-sky country surrounding it. (Drive north from downtown and you reach real Canadian wilderness in almost no time.) In its way, Toronto feels like a frontier town—one that’s in the midst of a cultural gold rush.
Queen West is the apotheosis of the city’s new energy, a swath of row houses and former factories reminiscent of London’s East End or parts of Brooklyn. This is where you’d want to move if you were young and in a band. “My joke was always that you couldn’t find a roll of toilet paper, and now you can get an ironic Sonic Youth onesie for your baby,” said singer Emily Haines, of Metric and Broken Social Scene, a longtime Queen West resident.
On weekends the neighborhood feels like a playground for street-style photographers—not surprising given the ever expanding collection of fashion boutiques. Besides Matt George’s Nomad, there’s Sydney’s, which carries men’s wear from Dries Van Noten, Jil Sander, and Japanese brand the Viridi-anne; and the local label Klaxon Howl, which, in addition to vintage military gear, sells its own men’s clothing: stiff selvage denim and chinos; flannel scarves; ultra-structured shirts. It’s the chic, woodsy look: wear it the next time you’re hiking to a model casting.
For all the global brands, there’s a distinctly local flavor to Queen West—this isn’t Hipsterville, Anywhere. The neighborhood’s two standout hotels, the Gladstone and the Drake, both feature Canadian artworks; at the former, a different Ontario artist decorated each of the 37 guest rooms, while the Drake employs a full-time curator and rotates its collection throughout the hotel every month. Both properties were 19th-century Trunk Railway lodgings that had fallen on hard times before being renovated. Jeff Stober, who bought the Drake in 2001 and reopened it three years later, sees the hotel as a cultural space for Torontonians. “As the downtown core becomes more dense, you can only do so much entertaining in your personal living spaces,” he said. “What happens by default is that the city becomes your living room. From store owners to restaurateurs, everyone recognizes that this is a really good place to pitch a tent.”
Or to build a brand. Stober also owns three shops—one of them attached to the hotel—called Drake General Store. Their stock capitalizes on a groundswell of hometown pride, running the gamut from genuinely desirable stuff (Hudson’s Bay Company blankets) to Canadiana kitsch—maple syrup, red-cedar incense (which, full disclosure, I bought and love), and a decorative ceramic dish that reads I miss the old Blue Jays, a reference to the 1990’s glory days of Toronto’s baseball team.
This sense of affectionate irreverence is pervasive in the city. My favorite instance: a quote from the late journalist Pierre Berton, emblazoned in a hallway at the Thompson: “A Canadian is someone who knows how to make love in a canoe.” At the splendid Frank’s Kitchen, a small, chef-owned spot in Little Italy, half the menu reads like a caricature of what you’d think Canadians might eat: rare elk loin; rarer venison tartare. Both are fantastic.
Torontonians are effusive in promoting one another. After a tour through his Nomad boutique, George took me to a new boutique hotel in the Entertainment District designed by a friend of his named Del Terrelonge. Called the Templar Hotel—“as in Simon, not the Knights,” Terrelonge qualified—the hotel has 27 smartly decorated suites and lofts, a spa, and a chef’s-table restaurant called Monk Kitchen; deploys a Porsche Panamera as an airport shuttle; and features a lap pool with a transparent floor that’s positioned over the lobby’s lounge area.
When I asked for dinner recommendations, George steered me to Woodlot: bakery by day, restaurant by night, in a warm, inviting, bi-level space with Native Canadian artwork on the walls and a casually stylish waitstaff. Chef-owner David Haman’s style of cooking has been dubbed “urban lumberjack” by the Toronto press; though I was skeptical, his food turned out to be the finest of my trip. The bipartite menu offers both “Regular” and “Without Meat” options: whey-fed pork chop and steak on one side, caramelized Jerusalem artichokes and roast Japanese sweet potato on the other. Almost everything comes out of the restaurant’s wood-burning oven.
There wasn’t anyplace like Woodlot when I lived in Toronto. But the restaurant and its small-scale, artisanal approach seem to represent the future: a well-designed, thoroughly confident experience that respects Toronto’s heritage and simultaneously breaks new ground. There was no sense that the place was a knockoff or that it owed its menu and genial vibe to some other restaurant, in some other city. And thanks to the wood-burning oven, I left smelling like I’d been at a campfire. How Canadian is that?
Jonathan Durbin is a New York City–based writer whose work has appeared in Esquire, Paper, and Interview.