When did Toronto get so cool?

Canada’s biggest city is often overlooked in favour of Montreal or Vancouver. But these days, it exudes the kind of cool that can only come from not really caring.

“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.

Canada’s largest city has surprisingly few global chains. The exception is Starbucks, which has an outpost on nearly every downtown block, but why anyone would go to one is a mystery when the city has so many exceptional local franchises. At the bright and airy Dark Horse Espresso Bars you’re as likely to find small groups playing cards as typing on laptops. Then there is Balzac’s, a small chain located in unique, at times historic, locations around town. The one I visited was housed inside a 1800s pump house in the Distillery District, where I sipped a bowl-sized café au lait from a balcony overlooking an enormous chandelier.

My favourite coffeehouse was Kensington Market’s Café Panemar, with its retro-meets-industrial steampunk style, including track lighting of copper plumbing tubes. While devouring an indulgent chocolate cream cheese cookie under a large vintage “Viewing Booths 25¢” sign, I had my only hipster sighting in a three-day visit. There he was in a suit jacket, short tweed pants, 1940s-thin tie and leather satchel bag, with hair and glasses that seemed lifted from This American Life radio show host – and hipster demi-god – Ira Glass. He looked completely, ridiculously out of place and apparently word is spreading. Nonetheless I promised myself to come back during warmer weather, when the café opens its garage door walls to outdoor seating.

Panemar’s pipe lighting system could have been purchased at Metropolis Living, a large collection of refurbished and new furniture, functional art and you-name-it, located in a west Toronto area called The Junction, just north of the nearly 400-acre High Park. The first thing that caught my eye was a massive lamp – if you could call it that – made from an actual street lamp post. Then I was distracted by the vintage top hats, antique shaving chairs, glass hospital grade syringes, old prosthetics, phrenology busts, group portraits of 1920s mining camps and a plastic frog dissection kit. A nearby warehouse, Metropolis Factory, housed the bigger items, such as café signs and old timey stage lights.

As a fan of Monocle, the magazine publishing and broadcasting upstart that is a darling of the global literati, I couldn’t resist visiting the Monocle shop of overpriced sweaters, stationery and framed infographics. By choosing Toronto over Montreal or Vancouver as its only Canadian store location, Monocle has given the city its rarefied seal of approval.

I browsed through my Biblio-Mat purchase at barVolo, a bar of wooden communal tables below ornate brass lamps. It had two dozen beers on tap, many Canadian, including an outstanding cask-pulled Lone Pine IPA by an Ontario brewer called Sawdust City. I paired it with a warm, buttery pretzel, cheese board and various pickled bits and bobs, including zucchini and an egg. The night before, I drank my dinner with co-workers at Weslodge Saloon, which describes itself as a “modern air-cooled saloon” but reminded me of a Victorian hunting lodge with tiny lamps, gilded frames and laughable leather gun holsters worn by the staff. The beer options were decent, including some quality microbrews; and the jalapeño poppers, in which only one of every sixth pepper was fiery, made for a fun edible Russian roulette.

It was over dinner at Weslodge that I explained the origin of my theory that Toronto was anonymously cool. My wife and I had recently seen the 2011 film Take This Waltz by indie sweetheart and Toronto native Sarah Polley. Despite starring Michelle Williams and Seth Rogan, and having a deeply engrossing plot, no one seems to have heard of the movie. And as we watched it, pulled in by the melancholy ebb and flow of the characters’ complicated love lives, we kept asking ourselves, “What city is that? It looks so cool. I want to go there!”

We waited through the credits to be surprised by the answer.

While staying at the artist-designed, 37-room boutique Gladstone Hotel in the lively West Queen West neighbourhood, I used the iPad supplied in my motorcycle-themed room to look up exactly where Take This Waltz was filmed. The characters’ block of charming porch-fronted houses looked like where I’d want to live if I was lucky enough to spend more than two nights in Toronto. After a little digging I found the house; it was only a few blocks away. As I walked there, I played the song’s bittersweet anthem, The Buggles’ Video Killed the Radio Star, and standing outside the currently lived-in home from the film, I could only think of one word to describe the experience. Cool.