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 and 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 Art Gallery of Ontario is one of Canada’s most prominent art museums. Bonus: it was designed by Frank Gehry!
  • 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 Cafés

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.

  • 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
  • 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
  • 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 & 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

  • blogTO - Huge site with tons of resources. Everything from where to find Toronto’s best pierogies to guides on the best events and what to do.
  • Hip Urban Girl - Lifestyle blog from Toronto covering events, style, food and travel.
  • Toronto Life - Comprehensive site for locals, with restaurant and bar reviews that might be useful for tourists.
  • 1 ❤ T.O. - Blog which includes stories, reports and reviews on music, culture and style in Toronto.
  • Torontoist - News and lifestyle site about all the “interesting” things to do in and around Toronto.
  • Spotlight Toronto - This blog focuses on food and drink in Toronto.
  • Visit Toronto - The official tourism website
  • Canadian Tourism Commission - Canada’s official tourism portal which includes guides not just about Toronto, but the rest of Canada as well.

32 comments

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  1. Hip

    Wow cool but have you considered what all this is going to cost? Plus the city’s so disorganized, you might not even be able to find these things. The transportation is garbage so it’s an ordeal before you even begin doing the activities. And everything is just money, you have to spend to get all this. And for what? Something that is dull and boring. Any other city can have anything like these and there are no activities there that really surprises you. It’s just dull and boring which is all that the city is. Try going to a city that actually has colour as well as fun activities. Not a garbage dump with zombies walking around

  2. Jerry

    I wish I had of read this earlier! I just got back from a weekend there and was surprised how much we loved it. We stayed at this new boutique hotel, Be 650. You should check it out for your next trip. It was great, awesome service and actually really affordable. Surprisingly… ha

  3. You said: “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!”
    The Royal Ontario Museum (ROM as we call it) is a museum with artifacts and bones.
    The Art Gallery of Ontario ( AGO as we like to call it) is the place you meant, which has amazing art exhibits and events, and was renovated by Frank Gehry. Thanks. Peace!

  4. You said: “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!”
    The Royal Ontario Museum (ROM as we call it) is a museum with artifacts and bones.
    The Art Gallery of Ontario ( AGO as we like to call it) is the place you meant, which has amazing art exhibits and events, and was renovated by Frank Gehry. Thanks.

  5. JohnnyL

    I’ve read your article and even though I don’t consider myself a hipster I find it interesting. For me it is a refreshing and alternative view on stuff that can be seen or done around here in Toronto.
    Thanks especially for the tip on the White Squirrel Coffee, I’ve never heard about that one before. I love a good cup of coffee and I always like to discover new places where to get it.
    If I can give a few tips in return, don’t miss the Rooster Coffee House, or the BullDog Coffee (I’ve stumbled upon that one in this guide).

    • Good point Johnny.. And yes, I take quite a liberal definition to “hipster” when I use it here. Sound like some great coffee places, thanks for sharing!

  6. Great article. I agree, Toronto rocks. Great writer and guy to follow for Toronto art stuff is Vance Rollins. Great writer. @vancerollins

    • Fun video :) Thanks for sharing Aaron!

  7. I found recently I´m a hipster.(I found everything I like and do is called in this way..)
    I was looking for a city rich on hipster culture and vibrant.I hope Toronto could be this city. I don’t care about food and restaurants(I only care about have health food,no junky please…) ,I´m very worried about the night live,and dates and culture and about have much funny.
    I´m thinking about Barcelona or Toronto.
    I think both are good…

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  10. oliver

    Actually you have one thing wrong. Townies always pronounce the second t in Toronto. It’s people from outside the city and the suburbs that drop the t. That’s how you can tell where someone is actually from.

    • Oh good to know, Oliver. I admit that most of the Torontians I met were from outside the city…

    • Peter

      Hi, Oliver. I have lived in and out of T.O. for 43 years. As a ‘townie’ (term nobody uses), I can tell you, the ‘t’ gets dropped and not dropped regardless of geography. If someone says, “Tor-RON-Toe, yea, he might be new.

  11. Great post!

    I miss Toronto, I also miss Pizza Pizza for it’s cheap, but still awesome Pizza.

    • Pete

      What are you talking about? It was expensive as hell. If you get delivery it costs a fortune. Plus you have to pay a ridiculous amount of tax.

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  13. Thanks for the tips on Toronto. My brother is moving there next month and a visit may be in order! ;o)

    • Do it! You won’t be disappointed. Toronto is so, so cool!

  14. Yes! This article came at just the right time for me. We are visiting Toronto in a week and I have no idea what to expect or what to do. Will definitely use your tips! Thanks.

    • Glad to hear it Bobbi! Check out some of the Twitter users I mentioned above who may be able to give you suggestions on what interesting events and other goings-on are happening while you’re in town.

      Enjoy Toronto — I absolutely fell in love with it during my visit!

  15. Hi Adam,

    Glad to hear you had such a great time in Toronto and found our blog helpful! You really hit a lot of of my fave top spots. Tweet me if you’re ever back in town – so many more hidden gems that I would love to share :)

    Safe travels,

    Lisa

    • Thanks Lisa! I think it was @cdngrrleh who first pointed me in the direction of your blog. I definitely plan to return again soon — probably in the summer when weather’s a bit warmer. I’d love to find even more hipster hangouts in Toronto with you, thanks!!

  16. Hi Adam,
    Very nice post about my hometown. I’m glad you had a wonderful time and sorry we couldn’t meet. You hit all the right spots I think, I always recommend people to visit Queen west, graffiti lane, distillary district, and Kensington.
    cheers, Priyank

  17. Dial-a-Bottle and an entire museum devoted to shoes?! I must make it to Toronto although I don’t know if I would be courageous enough to do that rope dangling thing on the CN Tower.

  18. Great ideas Adam – even if I am in another age bracket. Those macaroons look amazing.

  19. Woohoo! What a great guide to trendy Toronto! I just had to recommend this to my twitter crowd. I’ll be there next year again and will look into the food scene as well. Will get back to your tips here. Thanks, Adam.

    • Thanks Monika. Definitely check out the food scene in Toronto, it’s only going to get bigger there!

  20. Good list! Black Hoof’s cocktail bar is actually named “Cocktail Bar.” (I know, confusing). Black Hoof and Raw Bar are beside each other across the street. I can’t believe you found out about Dial A Bottle. Hilarious! What bar was giving away Hawaiian leis?!

    • Adam

      Hey Natalie! Thanks again for all your suggestions. Good to know about The Black Hoof – I remember the sign outside of it just said “Cocktail Bar” and we were skeptical we’d found the right place when we got there.

      Some dude in a pizza shop over on Church Street told me about Dial A Bottle at like 3am when we were desperately looking for more booze! Such an incredible idea but I was less sure they’d deliver to my hotel room, haha.

      And no clue which bar it was with the leis…can’t remember where it was :)

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