Toronto City Breaks ~ A Local’s Guide on What to See & Do in Toronto!

Sitting on Lake Ontario, Toronto’s skyscrapers, neighbourhoods and natural beauty form the backdrop for a potpourri of cultures. Rachel Lissner reveals the best of the city, from the Caribbean festivals to the Japanese rockabilly bars…

You’ve seen it in movies as New York, Chicago, Washington DC, and even Moscow, but it’s not just Toronto’s appearance that is diverse: nearly 50% of residents living in Canada’s largest city were born outside of the country, and this amazing conglomeration of cultures is no doubt what contributes so much of the city’s character and verve.

With residents taking an increasing interest in urban planning and municipal politics, Torontonians have really embraced their city as a place they can develop themselves. Citizen engagement is on the rise and every year more and more initiatives (such as car-free neighbourhoods) are undertaken, whilst festivals celebrating everything from kites, streetcars and the urbanist Jane Jacobs (a former Toronto inhabitant) have all popped up.

Toronto is a city of neighbourhoods, so despite sprawling itself into fifth place of largest cities in North America (with a population of 2.5 million), every area downtown and beyond feels like a microcosm of the city itself. In a day, it’s possible to travel from Poland to Korea to Portugal to Ethiopia to Greece and beyond. Grab a day pass for (about $12) and go for a spin around the world!

Best of the Beaten Track

Toronto’s iconic skyline is dominated by the CN Tower, which is expensive to visit, and touristy to boot. But it does have 360° views and one of the best restaurants in the city – and a meal there includes a free elevator ride up the tower. For thrill seekers who want a breath of fresh air, the Edgewalk is your chance to go for a stroll on the outside of the CN Tower. Just be sure to reserve in advance.

Get a fix of Canadiana at the Art Gallery of Ontario, which recently got a stunning makeover from Torontonian starchitect Frank Gehry. The AGO has one of the best collections of work from the Group of Seven, Canada’s emblematic group of landscape painters from the 1920s and 30s. The Powerplant and MOCCA have contemporary collections and are free to visit. (If you’re up for a road trip, the McMichael Gallery in picturesque Kleinburg has another stunning collection and even more Canadian works).

Toronto Island is a nice retreat from the city and it’s just a short and cheap ferry ride away. Hit up St Lawrence Market, one of the largest markets in Canada, or Kensington Market, a colourful neighbourhood (see Hipster’s Guide below for more!). Bring a bike, and enjoy a sunny day picnicking and hitting the beach.

The Distillery District is also worth a walk around, or you can even go for a spin — the Segway tours are based here. The architecture is beautiful and every building houses classy shops and nice restaurants. The Distillery District was once the largest distillery in the British Empire and is often the set for films, like Chicago.

Casa Loma is also nice for a walk, if you can get past the hefty entrance fee. Toronto’s very own castle was erected by a megalomaniac who turned the keys over to the city when he was no longer able to afford building it. It’s another popular film location, so maybe you’ll recognize it.

If you want to go to Niagara Falls (which is as touristy as you imagine), make a day out of it by doing a bicycle tour of the local wineries — you’re in one of the best wine-producing spots of the continent! And if you want to enjoy the water in tranquility, the quaint beaches in the East end are a real treat, as is the Queen Street East streetcar ride to get there.

For more ideas on how to spend your long weekend check Get Your Guide, who list scores of great tours and activities on their easy-to-book website.

Hipster’s Guide

Go west, young man, to find the hip parts of Toronto. Kensington Market is the Christiania (see our Copenhagen guide!) of Toronto. Colourful murals, independent food stores, tonnes of bars, and a little bit of every cuisine is squeezed into these handful of streets. Expect the people to be as colourful as the murals and the murals to be really, really colourful. While you’re there, go vintage shopping on Kensington Avenue, fuel up at Pamenar for coffee, grab a bite to eat somewhere on Augusta Avenue, and visit Cold Tea for a drink.

Walk, bike, or take the streetcar along Dundas West, to the rapidly changing area of Little Portugal. Spend some time in Trinity Bellwoods, Toronto’s peaceful yet buzzing central park, and visit Nadege on the southeast corner for the best macarons in the city, and Type, a fantastic independent bookstore with Canadian lit.. West of the park is Ossington Avenue, synonymous with absolute hipsterdom these days. There are a some good vintage shops and restaurants here, but you should really return by night when you’ll have your choice of bars to visit.

Once you hit Queen Street, take your time crawling from the area called Queen West to West Queen West and visit all the independent boutiques and art galleries, and admire the typical Toronto architecture along the entire stretch. Keep going and you’ll pass the Drake Hotel, the Gladstone, and eventually Parkdale, the westernmost hip area.

Parkdale is perhaps the most interesting neighbourhood in terms of populations, as it’s filled with many, many immigrant groups, “starving” law students, impoverished people, baristas, and now DINKs. Some of the most popular restaurants in the city are here, like Grand Electric, as well as some great holes-in-the-wall, like Bacchus Roti. Parts and Labour is here too, if you want to amplify your coolness up to 11.

For even more hip ideas check our Secret Seven things to do in Toronto.

Experience & Events

The biggest event of the year is the Toronto International Film Festival every September, a two-week cinematic whirlwind of the biggest films, most famous celebrities, and red carpet.

Toronto also hosts Jane’s Walk, a weekend of community-lead walking tours the first weekend of May, Pride, a week-long celebration of sexuality in July, Caribana, the largest Caribbean culture festival in North America in August, and Nuit Blanche, an all-night contemporary art festival around the end of September or early October.

On the smaller scale is Pedestrian Sundays in Kensington Market in the summer months, which closes off the neighbourhood to cars and opens up the streets to giant-sized Scrabble, food vendors, samba bands, and artisans. More regular is the Toronto Underground Market, a monthly event of pop-up food vendors at the Evergreen Brickworks, an old brick factory that has been renovated as an environmental and arts space.

Year round you can hear stories from locals on your cell phone by calling the numbers on the Murmur signs. It’s a project that started in Toronto and has expanded all over the world.

Pillow Talk

Planet Traveller is Toronto’s greenest, newest and best-located hostel, situated at the top of Kensington Market.

Close by is the Baldwin Inn, a tiny family-run bed and breakfast in Baldwin Village, a small hub of restaurants around the corner from Chinatown and the Art Gallery of Ontario. In the summer the garden is a nice retreat from the heat. If it’s full, check the Beverly Place another B&B just up the street.

For those looking to splurge, head west to an area known as West Queen West. The Gladstone Hotel is a beautifully restored hotel in Toronto that also curates a nice art collection and hosts a variety of events, from karaoke to book readings to 1950s dance nights.

Just a block or so away is the Drake Hotel, which is also a boutique hotel but has an edgier, rocker feel to it – making it the hipster’s choice.

Fork Out

Eating out in Toronto is like spinning a globe and buying a ticket to wherever your finger lands. Brunch is a legitimate sport that Torontonians take seriously. Aunties and Uncles is undoubtedly the kitschy-est, greasiest, and most popular spot around. It’s open every day and it is advisable to save it for a weekday.

On the weekends head over to Starving Artist, where everything is served on a waffle.

If you need a pick me up, head over to Pamenar in Kensington Market for some of the best espresso and people-watching in the city. They have the best patio and backyard in town.

Zocalo is a great spot to go for any meal and it recently got a nod in the New York Times. The menu is seasonal, locally sourced, and a total steal with entrees under $15.

Want something cheap? New Generation Sushi in the Annex offers the most bang for your buck.

For a late night feast, pop over to Poutini’s for some poutine, Canada’s most famous dish, a bed of fries covered in gravy and cheese. It’s open every day, and until 4am on the weekends. You can thank me later.

Drop In

Toronto nightlife is as varied as the people that live here and if you have the energy for it, you could dance yourself silly every night of the week, no matter what flavour you savour.

Every Wednesday She Does The Cityposts a weekly “Hit List” that has the most comprehensive guide to the weekend’s events.

In general, the entire strip of Ossington between Dundas and Queen is the current epicentre of drinking, Instagramming, and drunk dining (shout out to the fried pickles at the Lakeview).

The Communist’s Daughter is the best spot, but you’ll be lucky if you can grab one of their 30 or so seats (along with one of their delicious pickled eggs).

The Dakota Tavern, Sweaty Betty’s and the Painted Lady are all good bets, as are the places spilling over on Dundas, like the Japanese Rockabilly bar, Black Dice.

For 60s retro head over to Shake, Rattle, and Roll at Clinton’s or Shake-A-Tail at Sneaky Dee’s, every Saturday. ($5 cover and long lines if you’re not there early).

If you want to see and be seen, Drake Hotel is one of the best cocktail spots in the city and always packed on the weekends.

Toronto is also ground zero for Canada’s gay clubbing scene. In the Village (also known as the Gaybourhood), Slacks, Buddies in Bad Times, and Crews and Tango are always packed. If you’re more into the ladies, head west to the Hen House, where you can also have great brunch on the weekends, if you get my drift.

Getting There

Pearson Airport is about an hour away from downtown by public transit ($3), but a car can take about 20 minutes. Air Transat always has the cheapest prices to and from Europe. For the Americas try Porter Air, based out of an airport in Lake Ontario. It serves Canadian and American cities in the east, including Chicago. By bus, Ottawa is four hours away, Detroit and Montreal are five hours away, New York is 12, and Chicago is 14. MegaBus and Greyhound are your best bets. It’s also not a bad idea to fly into Buffalo and take MegaBus from the airport. Travelling by train is expensive but Via Rail sometimes have sales.

More Juice

Check out Torontoist for what’s going on in local affairs, local history, and all things Toronto. She Does The City’s Hit List has the best roundups of nightlife from Wednesday to Sunday every week. If you are interested in the dining scene, Toronto Life gave you a taste of restaurants in any neighbourhood and every budget level. Yelp is also really handy.

Hard Copy

Canadian literature is a genre that is small but mighty. See how literature is mapped out at 49th Shelf. The Scott Pilgrim books serve Toronto justice with its real love of the city and spot-on illustrations, whilst Michael Odaantje (author of The English Patient) provides a backdrop of how the city was built in In the Skin of a Lion. If you want to learn about the city itself, check out Shawn Micallef’s Stroll.

Silver Screen

“There it is, men. Toronto. It’s beautiful.” As mentioned before, Toronto is often seen on screen, just not as itself. But don’t think we’re always the bridesmaid: Reel Toronto is a column on Torontoist that acts a location scout for movies that were filmed here but set elsewhere. Mean Girls, Billy Madison, Blues Brothers 2: Toronto. Toronto has set the stage for Take This Waltz by Sarah Polley and, of course, Scott Pilgrim, but Toronto’s golden boy is Atom Egoyan, whose film Chloe is considered the quintessential Toronto film. But if you really want to see Toronto, Canadian Bacon proves that we’re not just “New York but without all the stuff” that “30 Rock” claims. Come on, when did John Candy ever steer you wrong?

Soundtrack to the City

Spadina Bus – The Shuffle Demons
This Lamb Sells Condos – Final Fantasy
Old Apartment – the Barenaked Ladies
Parkdale – Metric – One

Video Inspiration

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