Have you ever been completely surprised by a city? Ever arrived somewhere and been immediately floored away with the options for things to do or places to eat at in a city? Or overwhelmed with literally hundreds of options for bars and clubs worth visiting? For me, that was Toronto. I’d heard it was a cool city from many of the expats I’ve met abroad, but I just didn’t know until I saw it for myself. I’d heard Toronto called “a cleaner version of New York City,” and after visiting both cities in the span of a month, I’d probably have to agree. (Admittedly, Toronto is much smaller than NYC…)

Toronto is cool. So cool, in fact, it’s quickly become one of my favorite cities. Toronto is a BIG city with a population over 2.5 million. It’s also a very international city. In fact, just over 50% of Toronto’s residents weren’t even born in Canada! In a city with so many foreigners, it shouldn’t be surprising that Torontonians speak all together over 140 different languages.

In a city as international as Toronto (rated one of the most multicultural in the world), it’s no surprise that there are plenty of hipsters and hipstery things to do. With art fairs, a growing food truck scene, three Chinatowns and a diverse and multicultural population, Toronto is one of the world’s most hipster cities. Here are my picks for some of the best things to do including tourist attractions, restaurants, bars, cafes and nightclubs. And if these personal recommendations aren’t enough, check out Toronto’s official tourism app which highlights current attractions and events.

Things to do, places to see…

• Queen Street West is undoubtedly one of the most hip and trendy areas in Toronto today. The Trinity Bellwoods Park seems to be the hub of summertime activity for the neighborhood. Though Queen Street West was once more bohemian, gentrification has caused rents to go up but it’s still full of hipstery cafes, bakeries and restaurants.
• On a side street just off Queen Street West is Graffiti Alley—Toronto’s only public space where graffiti is legal. You can even take a tour of Toronto’s graffiti scene which will give you more insider tips on the scene.
• For art lovers, the Royal Ontario Museum is one of Canada’s most prominent art museums. Even if you don’t go inside, the outside is spectacular enough!
• Maybe because Toronto is so close to NYC, the city is one of Canada’s most fashion-savvy. There’s an entire museum dedicated to shoes!
• If you’re looking for an awesome photo opportunity, shell out the big bucks and do the EdgeWalk at the CN Tower. It’s the tallest free-standing structure in the Western Hemisphere (that’s HALF OF THE WORLD). Perhaps because Canadians are just so adventurous (or they have a strong desire to try to cheat death) they’ll let you walk around the tower at 116 floors up…with little more than a rope keeping you attached to the building.
• Get lost in Toronto’s Chinatown. You can find just about any fruit or vegetable at the fresh market stands, but tuck in between them and you’ll find the city’s best Chinese restaurants. Come for Dim Sum if you can!
• Go shopping near Kensington Market
• Toronto, being one of Canada’s many epicenters of culture, is home to one of the world’s most important film festivals—lovingly abbreviated as the TIFF. The Toronto International Film Festival lasts 10 days and celebrates some of the best films and documentaries from around the world. They’ve got quite a reputation for selecting quality movies which end up as blockbusters or critical hits.
• Toronto’s Distillery district is home to art galleries, restaurants and beer gardens. The brick-lined streets are reminiscent of Victorian times, but hey, this is the now. You could do a Segway tour in the Distillery neighborhood, or you could pound back some beers. You decide.

Restaurants and cafes

Toronto’s culinary scene is as diverse and interesting as the city itself. Many restaurants have embraced current food trends—everything from vegan restaurants to cupcakes and even honeybees! There are plenty of ways to get associated with Toronto’s food scene. Personally, I took a chocolate and cheese food tour with @chowbellaTO which was a great introduction to the Queen Street West hipster neighborhood of Toronto.

• Tealish — This little tea shop and café is a small delight on the trendy Queest Street West. Their loose leaf tea has become so popular over the years, it’s exported all over the world. They’ve even got a chocolate flavored tea! — tealish.com
• Dlish Cupcakes — Often rated as Toronto’s best cupcakery, Dlish has a rotating menu of cupcakes with a few constant regulars. Go for the classic (and their specialty) Red Velvet which is made from high-quality imported Belgian chocolate. — dlishcupcakes.com
• White Squirrel Coffee — Fair trade, organic coffee. Can’t get much more hipster than that. — whitesquirrelcoffee.com
• Food trucks — Still a growing scene in Toronto, and they still need legal permits to park on the city’s curbs. But the city is beginning to catch on. This summer, @ontfoodtrucks hosted the city’s first annual Food Truck Awards. For a full list of the food trucks in Toronto, and alerts on their location, visit torontofoodtrucks.ca or learn a little bit about Toronto’s complicated affair with the food truck scene on pinkmafia.ca
• Charlie’s Burgers — This invite-only restaurant is too hip and too secret for me to have figured it out. Their website simply asks for an e-mail address, but there have been plenty of features and exposés on the pop-up (and top-secret) restaurant.
• Nadege — Gourmet French pastries and dessert shop. Try the macaroons (see photo above). — nadege-patisserie.com
• Cheesewerks — A relative newcomer in Toronto’s restaurant scene, this restaurant focuses solely on one item: grilled cheese. You can get each sandwich (named after a travel destination relevant to the owner’s own personal history) as a mac & cheese dish, too, if you wanna skip out on some of the carbs. Try the house-made soda and if you’re with a group, go for the fondue, too! All food at Cheesewerks is made from 100% Canadian products.
• Pizzeria Libretto — A super local neighborhood restaurant that serves a real Neapolitan pizza. Often considered a local favorite! pizzerialibretto.com

Bars and other nightlife

This is just a small selection of the many Toronto bars and hipstery clubs in the city. There are literally hundreds if not thousands of great places to go out for a drink in the city.

• Ossington is far and away Toronto’s most hipster neighborhood and area. Ossington street runs perpendicular to Queen Street West which has been a bit yuppified over the years, but Ossington has kept its roots for the moment. You’ll find some of Toronto’s most hip bars on this street. Plenty of people regard it as too hipster, but so long as you go out with a funky hat or tattoo sleeves, you’ll fit right in. One night out, I wandered into a bar that was giving away Hawaiian leis and was packed full of bearded, flannel-covered hipsters. It was awesome.
• The Black Hoof — Arguably Toronto’s best cocktail bar, The Black Hoof is a tiny little place on Dundas Street West. If you can’t get into the lounge and don’t want to wait for a seat, they’ve got a raw bar across the street. Start your night out here with a classic cocktail before things get sloppy.
• Cold Tea – This dive bar is hidden down a mysterious hallway near Kensington Market. The hideaway speakeasy bar is hard to miss because of the thumping music and the crowd of hipsters waiting outside under a red light. There’ll be a DJ at the bar inside, and a large patio out back. Get a cocktail!
• 416 Snack Bar — Popular for their small plates and sort-of tapas, the food is good, the bar is crowded and the drinks are plentiful! Great for parties and groups even if it’s overflowing with yuppies and hipsters. Check out their blog or find their daily specials on Twitter @416SnackBar.
• Drake Hotel — Located on Queen Street West, the boutique hotel has one of the area’s trendiest bars to boot! Even if you’re not staying in one of the hotel’s beautiful rooms, go for a cocktail (or two).

Gay Toronto

Toronto is one of the most gay-friendly cities I’ve visited and it’s easy to understand why. The city, with its huge ethnic and multicultural population is one of the most tolerant in the world. With so many different types of people and cultures coming together in one space, the city has embraced tolerance to an extreme. The Toronto pride festival each June is one of the world’s largest. Most of the gay nightlife is in the city’s “Gayborhood” on or nearby Church Street.

Travel tips

• If you want to sound like a real Torontonian, don’t pronounce the second t in Toronto!
• Skip the American-style restaurants near Kensington market and head straight for the ethnic cuisine (especially the churros!)
• Have your beer and spirits delivered to your door! Due to the beer and alcohol laws of Ontario, all alcohol must be purchased through a government authorized shop, however services like Dial a Bottle offer delivery if you’re not near a spirits shop.

Local blogs for more insider tips

Toronto Twitterers

Special thanks to the local bloggers who suggested many of these hipster things to do in Toronto. This post was brought to you in part with the help of the Canadian Tourism Commission & Visit Toronto.

Visit my other hipster city guides from around the world here.

By Adam Groffman

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