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Toronto Hipster City Guide for Travelers

Canada’s coolest city is also one of the best in North America. You just might be surprised at Toronto’s diversity and the amount of awesome bars, restaurants and events which make the city so unique

Hipster Guide to Toronto - Travels of Adam -

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 in Toronto

Hipster Guide to Toronto - Travels of Adam -
  • 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.

Is Toronto a cool city? With all its hipster bars and fun & trendy things to do, Toronto is one of North America’s coolest cities.

Restaurants and Cafés in Toronto

Hipster Guide to Toronto - Travels of Adam -

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. —
  • White Squirrel Coffee — Fair trade, organic coffee. Can’t get much more hipster than that. —
  • 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 or learn a little bit about Toronto’s complicated affair with the food truck scene on
  • Hipster Guide to Toronto - Travels of Adam - — 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! —
  • 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). —
  • 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!

Toronto’s Best Bars & Cool 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).

Toronto Gay Travel Guide

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.

Where to Stay in Toronto

Hotels in Toronto fit into a number of different categories. Because Toronto is a popular business destination, you’ll find a lot of chain hotels and skyrises in the city center—convenient to the conference centers and other business hotspots.. TripAdvisor is a good place to check hotel reviews for additional recommendations, or for those looking to stay in a rented holiday apartment, Airbnb is still one of the best options with apartments available from $70 per night.

Best Hotels in Toronto

  • Victoria Hotel — Located on the popular Yonge Street, this 3-star hotel is a great budget value. Rooms come with mini-fridges and other basic business amenities—great for keeping your trip affordable on a leisure holiday. Room rates from $90 per night.
  • Gladstone Hotel — This historic hotel has all the essentials required for a comfortable stay. Plus with easy access to a fitness center. Staying at the Gladstone Hotel, you’ll be near Toronto’s Chinatown and Queen Street West (one of the best areas to hang out for nightlife, cafes and restaurants). Room rates from $150 per night.

Toronto Travel Tips & Other Things To Do

Hipster Guide to Toronto - Travels of Adam -
  • 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 Toronto 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.
  1. Summer lovin'—art and food festival in Toronto's trendiest neighborhood | Travels of Adam - Hipster travel around the world says:

    […] Ultimate Hipster Guide to Toronto […]

  2. Natalie T. says:

    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 says:

      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 :)

  3. 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.

    • Adam says:

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

  4. Leigh says:

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

  5. Suzy says:

    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.

  6. Priyank says:

    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

  7. 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,


    • Adam says:

      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!!

  8. 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.

    • Adam says:

      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!

  9. Liv says:

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

  10. […] Toronto, Canada “Toronto was one of the most surprising cities I visited in 2012″- Adam Groffman […]

  11. Matthew Challis says:

    Great post!

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

    • Pete says:

      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.

  12. oliver says:

    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.

    • Peter says:

      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.

    • Adam says:

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

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  15. Kim says:

    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…

  16. aaron says:

    Very helpful!!! i was just in toronto and Niagara falls area’s for the weekend with my friend and i documented it and made a Vlog about it!!! check it out :)

  17. Jason says:

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

  18. JohnnyL says:

    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).

    • Adam says:

      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!

  19. Christine U says:

    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.

  20. Christine U says:

    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!

  21. Jerry says:

    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

  22. Hip says:

    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

    • Iain says:

      Do you mean actual “zombies”? Because the Toronto Zombie Walk is another fantastic event that takes over the streets close to Halloween. One of the many strange and colourfull events happening in Toronto every weekend from May to December.

      It Toronto is “dull and boring”, I’m not sure anyone can possibly take your opinion seriously.

  23. Max says:

    “Hip” is clearly an embattled Toronto trol–I mean– resident, who has rarely lived outside of that city… or he is from Montreal or Vancouver. ;)

    Speaking as a native of Toronto who has lived in New York, Los Angeles, Montreal, San Francisco and London, (UK not ON), I refute most of what he has to say about the city. It is undergoing huge development right now, which is kind of a bummer, but it has also transformed the city into its holy grail: “world class”.

    You can’t find festivals as grand as Caribana or as friendly as Pride Week anywhere in this continent. You can’t find a city as multicultural and as integrated on this continent either. There is a multitude of great restaurants that never would have existed when I lived there 15 years ago. The Distillery and Harbourfront offer some of the best “by-the-water” experiences rivaling Chicago and San Francisco.

    As for public transportation, try living in L.A. As for expense, try living in San Francisco or Vancouver.

    Also, try not being so generalized and reductive in your posts.

    • Adam says:

      Thanks for the defense Max! Toronto is definitely a cool city and has some really fantastic qualities other cities are sometimes missing – and you’re spot on about the diversity. I think it’s what makes Toronto really special.

  24. Constatine says:

    Toronto is hip in the first 6 weeks of fall and the last 6 weeks of spring. Winter is just too cold and summer is just too hot and humid. Its has a very long way to go to consider itself a serious world class city. It requires at least another 50 years to catch up to New York in infrastructure; by that time New York will be another 50 years ahead. I bring up New York city because wherever you go you hear Torontonians comparing this and that to New York city. Its just terrible. Why would you want to mimic another city when supposedly yours is better? I got sick and tired of hearing this throughout my life in Toronto and simply moved to the real deal; New York.

  25. Alanna says:

    Hi Adam, Great post thanks. Curious where you would recommend staying..Thanks!

  26. Excellent way of explaining, and nice article to get information regarding my presentation topic, which i am going to deliver in school.

  27. Michael says:

    As much as the TTC (public transit) is bad it pains me to hear people talk of it in a negative way. People in Toronto get it… is bad we know it, we know you know it, but no one says horrible things about it. Leave 30 mins early because “it’s the TTC”. When the driver hops out with a metal crowbar to change tracks just laugh and say “it’s the TTC”. Or when metal rod gets dumped off and there’s sparks flying everywhere laugh and turn to your neighbour and say “it’s the TTC”. When you get kicked off a street car for no apparent reason the person next to you will say “it’s the TTC” this saying strikes up conversations and humour! And if you are a local, and only if, you may go as far as saying “F$&@ the TTC”. Despite all of this the TTC is like a aunt that you love but she gets on your nerves. So please keep a positive mindset when dealing with our hated and beloved TTC.

  28. Michael says:

    And as for the haters of our city….please by all means go to New York and stay there!

    I love toronto like no other, wake up and get a freshly roasted coffee bean coffee. Or an Americano on any street corner. At work there are hundreds of dishes you can order from your desk to be delivered hundreds of different ways….bicycle, disabled persons, uber…etc. On your way back from work catch a cheap a beer anywhere and then a slice for pie in the sky or a crappy caplansky’s. Go to a Portuguese bakery, italian bakery, polish bakery’s, middle eastern bakery, or all of them for dessert. Then heck you will be hungry again at 9 so get some mother’s or a pho bowl. On your way home from that stop by the ever so pleasant Harry Potter bar or the Gladstone to get your pump of hipster happiness. So haters you can stuff your mouth full of our toxic Lake Ontario water and shove the tower right up your behind! This is the 6 we have a god so please pass us by and hit up New York because we are happy with what we have….we will try and show you what we see in our city but if you wanna “New York it” then that’s on you.

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  30. Emil says:

    Nice tips:)

  31. DatingGuy says:

    Been to T dot twice, first time didn’t really know where to go and thought it was just OK. Second time did some quick research and loved it, can’t wait to go back next summer.