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“Clock-clock-clock-clock-KUHwhoomp!” That was the sound of the Biblio-Mat, a one-of-a-kind refrigerator-sized book vending machine, as it dispensed random titles for $2 Canadian. It was tucked into the back of Monkey’s Paw, a small rare books shop in Toronto that displayed a collection including, when I browsed there last May, a 1965 shopping directory of India, a pictorial history of the carousel, a volume of “gesture poems” and a 1955 booklet of cake recipes made with the “new Kraft Oil Method”.

The vending machine was merely a clever way to sell bargain bin titles, but I’ve never been more thrilled to receive a book I didn’t particularly want. I lugged my heavy, spine-ripped volume of the Romance of Medicine all the way back home and gifted it to my brother-in-law, a doctor.

“Cool,” he said after opening it. I told him where and how it was purchased. “Cool,” he said again.

I had to agree. As far as Toronto’s coolness goes, that’s just the start. After all, the definitive, if circular logic of coolness is that cool things don’t need to convince anyone. They don’t even care. Because they’re cool.

That’s why Toronto is cool: it has been for a long time, and since it doesn’t feel the need to advertise the fact, most of the world doesn’t even know. Canada in general is understated in this way; it’s not very Canadian to point out one’s own awesomeness. Toronto is so cool, it might not even know it is.

“That’s a good one!” laughed Monkey’s Paw owner, Stephen Fowler, when I asked him about the city’s transition to urban hipness. “I first came here [on vacation] from San Francisco, known as a cool city, in 1998,” he said. “I was expecting to find the most boring city in North America.” Instead, he found it was indeed “cool”. Surprised to be proven wrong, he moved to Toronto four years later.

Compared to the architecture and French culture of Montreal or the beauty found surrounding Vancouver, Toronto has never been particularly alluring. Tucked into the northwest corner of Lake Ontario, one of North America’s Great Lakes, the charm of Toronto is found in microcosms of hipness: in relaxing coffee houses, arty hotels, eclectic shops and quiet bars. None are obvious. All must be sought out.

After checking into the Drake Hotel, a warren of 19 “dens”, “salons”, “crash pads” and a single suite, each with a Wes Anderson aesthetic, I found my key didn’t work. Back at the front desk – which loans hotel guests indie-rock -loaded iPods and hotel themed DVDs such as Four Rooms, Faulty Towers and Psycho – the front desk clerk gave me a new key, plus a free drink token at the bar. The hotel’s Lounge, which staged the Canadian debut of many 1980s punk bands, has a wall piled with old hi-fi stereo equipment and an ambitious drinks menu. I sipped the candy-sweet Deliverance, made with cedar-infused bourbon, apple brandy, Fernet Branco, apple liqueur and (the reason I picked it) Canadian maple syrup. Back in my home of Brooklyn, New York, this combination of highly inventive cocktails and meticulously arranged décor would be fly paper for moustachioed hipsters sporting diminutive hats and tartan vests. Instead, as I sipped my Deliverance, an all-ages, hockey apparel-clad crowd cheered as a game played on a big screen above the fireplace.

My room, decorated with clunky metal chairs and a 1960s-era desk, also came with a “pleasure menu” of erotic toys and films – plus a copy of The World’s Coolest Hotel Rooms, which, in a surprising bit of braggadocio, featured the Drake. Less cool about the Drake: walls are thin enough to hear other guests enjoying their orders from the “menu”.

Earlier that day, I took a light rail street car across downtown to the Rooster Coffee House, a small space with a communal table serving fresh, filling baked goods – including a drool-worthy blueberry scone – and high-end Intelligentsia coffee in charmingly mismatched mugs. On my commute I passed the TIFF Bell Lightbox, host of the Toronto International Film Festival, famed for picking movies that win Oscars.

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