Travelling In

Toronto: A Guide

  • Words. Bridget Douglas

Editorial | May 15 2017

Just across the water from Buffalo, New York, is the Canadian border. From there, it takes about two hours to get to one of the coolest cities in the world: Toronto.

This absolute gem of a cultural paradise is right above the US, and the average American knows hardly anything about it…except maybe that it’s where Drake is from.

My boyfriend and I recently went there and stayed at an Airbnb for four nights. We had been there once for one night during one of his band’s tours, and found that the people were nice, everyone was active, everyone had dogs, and there were lots of cool restaurants, cafes, and music venues. So we went again to get more of a feel for it…and to see if it’s a place we would want to live.

Basically, the art scene, music, food, architecture, and culture in Toronto are off the chain, not to mention there’s great transportation.

It gets pretty cold in the winter though, which is the biggest downfall. Luckily for us, we were there at the end of March, so the weather was moderate. The summer is lovely though, you couldn’t ask for better weather.

First of all, Airbnb is the shizz, it’s the new motel or cheap hotel. It was our first time using it, and it was so amazing. We were right in the coolest part of town: between Queen West and Ossington Avenue, and our host even left us food and all kinds of goodies (Netflix, too!).

As for exploring the city, the best way to see a city is to walk, and walk, and walk. But also to check out local websites that list the best neighborhoods and that map everything out. For Toronto, the best site for that is BlogTO, I can’t stress that enough.

We didn’t get to see every neighborhood, but here’s a good taste of this wondrous city:


The two blocks of Ossington Avenue between Dundas and Queen, is probably the best strip in the city. You could spend all night just bar hopping on that one block. It’s jam packed with restaurants, cafes, and cute shops. The street is narrow, so there isn’t a lot of traffic going down it, which makes it chill and safe, and it’s surrounded by quaint residential streets. It was the first street we explored when we got there on a Saturday night.


After dinner and drinks, we were still hungry, and Bobbie Sue’s was just what we needed – a late night heated shack that serves up delicious Mac and Cheese. Situated on a residential street right off of Ossington and open ‘til’ midnight, they’ve got Pulled Pork Mac & Cheese, Carbonara Mac, Curry, and even Vegan and Gluten-Free options. We went with the Classic Five-Cheese Mac.


In the morning, we stumbled out of our downstairs cellar of an Airbnb of which the host lived upstairs, walked through the back courtyard and through the narrow alley, and walked a couple hundred feet away to Ossington. We went inside a killer interior accessory store called VdeV.


I literally wanted everything in there: Little terrariums, cool light up signs you can change the lettering on (our host had one that said welcome with our names on it), cool lamps and pillows – tis’ a delight for the senses.

Next: coffee.

Right across the street is Crafted by Te Aro.

It’s a tiny place, but a good amount of seating in the front and back. They have all types of coffee drinks. I got my new fav drink, Cappuccino with almond milk, and a Vegan Chocolate Banana muffin. Sitting

by the window looking out at the street was lovely. It was Sunday morning so lots of people were in there talking about their careers or what they did last night. Scott and I used the Wi-Fi to map out our route of exploration for the day because our phones couldn’t get service without it since we were out of the country.

Crywolf Clothing has the most enticing, colorful storefront, you can’t not go in. They have quirky clothes and accessories like skull keychains and nice little

notebooks with cute aliens on them. If you need an item with an adorable animated creature on it, this is your place.

Other spots we tried on Ossington: Hawker Bar, and Bang Bang Ice Cream. The bar serves Singaporean food, but we just had a drink. It was a quaint, cool place with red walls and tree stump bar chairs. The sign out front, pictured above, is what initially hooked me though: ‘PROVE THAT YOU LOVE ME AND BUY THE NEXT ROUND.’ Truer words have never been spoken.


Bang Bang is known for its amazing Ice Cream sandwiches. You go in and pick out the type of cookie you want, and the ice cream flavor, and make your own killer combination. Mine was a Ginger Cookie with Matcha Green Tea Ice Cream. Other interesting flavors are Olive Oil and Campfire Marshmallow.

Queen West

My idol, Anthony Bourdain did an episode of The Layover in Toronto and referred to Queen West many times during the show. This was another street super close to our place. We headed west from our place on Brookfield in search of the perfect dive bar.


We passed lots of wall murals, several art galleries and clothing stores, but it was past 7pm, so they were closed. Though I gawked at the window displays – Toronto knows a thing or two about how to please the eye.

I know what you’re thinking; it’s the rapper Drake’s Hotel! But unfortunately it’s not. The Drake Hotel opened in 2004, whereas Drake didn’t become famous until 2007. But, it is a very reputable establishment. It has an awesome bar and restaurant, and is known as ‘the place to see and be seen in Toronto.’ Across the street from it is the Drake General Store which has clothing, homeware, and other goodies.

We walked under an under pass, and it suddenly got seedier – I then knew we would find an interesting bar.

After walking by unassuming take-out joints of


various cuisine, that are probably way better tasting than their façade looks, we landed next to a duo of dive bars. There was Pretty Ugly Bar and Motel Bar right next to each other – which were we going to choose? Pretty Ugly is a little fancier with signature cocktails, and we’re not too fancy, so we chose Motel. It was very dark in there with records on the wall, and…drumroll…Pacman machine. Nothin’ like a little Bourbon, Pacman, and some Bob Dylan playing in a dark dive bar. I would love to try Pretty Ugly next time we’re in town though!

Dundas West

We spent a lot of time on Dundas West. It’s one of those streets in a city that make you go, ‘Wow, this place is something else.’ The road is wide and gives you a full view of the city. Corner bars and floral shops give way to hidden tree friendly streets full of early 20th century brick Art Deco homes that have a style you won’t see in any other city.

Walking up Ossington from Queen, you’ll run into Dundas West, which is also named the Little Portugal neighborhood for the large number of


Portuguese residents. There are still many Portuguese owned businesses, as well as Brazilian. It’s turned into one of the coolest areas with unique bars, restaurants, and vintage shops.

After our Motel Bar, Pacman fun in Queen West, we walked through old neighborhoods. The only glow on the streets came from the light in the living rooms lighting up the colorful stained glass above their windows. We passed an old rec center, and one or two couples making their way into the unknown of the night as we were. Dundas was our dinner destination.

We walked a few blocks on Dundas, observing every bar and restaurant, just checking the ambiance in there. There were so many to choose from. Yet at the same time the traffic was barely existent, but the nightlife was alive.

We finally chose Imanishi Japanese Kitchen, a really beautiful, bright space with lots of young people like us drinking beer, eating rice and miso soup.

It was a small menu, with the special that night being Scallop Nigiri. We had Plum Wine to drink which was very sweet, could barely taste the alcohol. For dinner, Scott got the Dote Miso which is Miso braised Pork Belly with a Boiled Egg. I got the Japanese Vegetable Curry Rice. Scott’s was killer. I later ordered a Bourbon and Ginger, which was the best I’ve ever had, really. They used Bulleit Rye and some good ginger ale.

The next night, we did dinner on Dundas again because it just seemed like the right thing to do. A place called Rhum Corner caught my eye. Scott loves Rum so I figured we should check it out. It was a Cuban restaurant with a small but appetizing menu. I kind of

like when the menu is small so you don’t have to think too much. We just split two appetizers, Macaroni Au Gratin and Bananes Frites which were Fried Plantain balls that came with a good sauce and some vinegar-y coleslaw. Oh yeah, and rum.

Kensington Market

The first time we came to Toronto, Kensington Market was the area that got us ‘saying Toronto is sick.’ We were walking down College Street to find something to

eat when we ran into this little enclave to the right on Augusta Avenue. It’s about two to three blocks of super hip shops, cafes, vegan bakeries, bars, all kinds of ish’.

It’s a haven for all of the college students to be lively, have fun and be artsy.

The University of Toronto is right around the corner, pictured above.

In the summer, the patio game is super strong in the city, especially Kensington Market. Café Pamenar has coffee and a full bar, whatever you’re in the mood for, and a beautiful courtyard. The doors open up from the inside to the courtyard which has vines going up the walls, making for a lovely space. We had some lattes and split a brownie inside on the edge of the courtyard.

Walking down the street, it’s a visual feast of colors and street art, all kinds of cool people, and organized wackiness. It was the spot I knew I had to come back to the next time I was in Toronto.

The first night we were there on our recent trip, we walked about two and a half miles, and I was in heels.


We ended up near Kensington Market, so it was really exciting to be there again.

It was a Saturday night, so things were happening. We heard good music coming from a place called Super Market, looked at the menu on the outside of the window, and decided to go for it. There was a band playing in a closed off back room, we sat in the restaurant/bar area. The seating was sort of lounge-y yet nice, high top bar tables, low lighting, a big bar, and the kitchen right in sight next to the bar.

There were young college girls having drinks, and couples on double dates, it was the place to be. I got fish tacos, and Scott got Poutine. Whether you want dinner, drinks, or see a good band play – this is your place.

Little Italy

Like Little Portugal, Little Italy doesn’t resemble Italy but rather a big Italian population with many Italian

owned businesses. It’s situated mainly on College Street West.

During our first trip, his band played at Sneaky Dee’s – a tex-mex restaurant/venue. It’s known as the ‘quintessential punk dive bar.’ After all, his band made close to $400 for a small show (they treat their bands well). The upstairs is the stage, and the downstairs is a full-scale restaurant with a little outdoor seating on the sidewalk. It has hosted popular Canadian natives like Arcade Fire and Feist. Punk + nachos + tequila = amazing.

During this trip, we had lunch right across the street from Sneaky’s at Nirvana. The décor is very bohemian with mandala paintings, gold and maroon walls, oriental lamps, and Buddhist faces on the wall. There’s a full Brunch menu served until 4pm. There

are tons of healthy and creative options, American/Canadian/ & Asian. Scott got a Breakfast Quesadilla, and I got the Scrambled Eggs & Potato Hash.

Then we just made up our way back to our area walking down College, checking out shops along the way.

Loon Records is a tiny vinyl store specializing in older stuff like Otis Redding and Bowie. The décor makes the place, with a big mirror in the back and rainbow lights around it. It makes you feel like you’re at home.

Soundscapes is a tid-bit bigger…okay, three times bigger. There’s a bigger selection, with a lot of new Indie bands, and even listening stations. By the door, there’s a list of shows in the city for the next two months, mostly of well-known bands. They’ve also got a good selection of music DVD’s and books.

Sellers & Newell is a fairly small used-bookstore, full of cheap and enthralling books.

It makes you feel like you’re in an old movie when someone goes in a bookstore and is in awe with the old and fascinating novels.

Gift shops are always the best place to find last minute gifts, and the perfect birthday card – Red Pegasus is one of those perfect gift shops. Chock full of fancy water bottles, donut pillows, funky jewelry, books, artsy glassware, and thank you cards like ‘Happy Birthday – You’re A Doll,’ with a drawing of Dolly Parton on it.

Going further, it turns more into a residential area with markets, grocery stores, and lovely neighborhood streets.


Our first morning in Toronto, we made the trek to the CN Tower. It wasn’t too far, but it was pretty windy, therefore cold. At first, we walked down to the water, Lake Ontario. It didn’t start raining until we got down there, of course. After that it got super cold. We walked a few minutes to the CN

Tower, on the way, stopping for gloves at a convenient store to shield from the wind.

We came up on this shrouding building with clouds engulfing the top of it. We went to the ticket booth to check prices, and the lady said there was no visibility at the top, so we didn’t do it. Honestly, I was relieved because I’m super afraid of heights. I’ve been to the top of the Empire State Building, and that was not enjoyable, the CN is over 100 meters taller. It is really a beautiful sight, and Toronto wouldn’t be the same without it.

The next day was sunnier, so here’s a cool picture of it in the distance. You can see the tower at any point in the city, so you can never forget that you’re in Toronto.

The next biggest destination downtown is St. Lawrence Market – this huge marketplace opened in 1803 as a public market, selling goods and meats from farmers and purveyors in and around

the area. Today, it is named one of the best food markets in the world. You walk in, and there’s a plethora of sausages, further its 100 different types of fish and cheeses, it’s a maze of foodie goodness. There are two floors. The lower level has several food stands, gourmet chocolate and dried fruits, breads and pastries – it’s an epic place. It’s open Tuesday-Saturday.

Queen Street East runs through the Downtown area. It has several shops, businesses, and restaurants, but its way more grungy and dirty than the other end of Queen. It’s worth a stroll for the underground vintage arena, Black Market. It’s seriously a huge space that

kind of resembles the lower level of a warehouse. They have tons and tons of band shirts for under $10. They’ve got vintage coats, jeans, dresses, and $1 beanies and gloves. Oh, and cool jewelry too. There was a whole row of $10 chockers of all colors and designs. It took everything in me not to get one.

Of course, it’s also where all of the big time Ad agencies, high end clothing stores, and more cool graffiti art are.


Other areas to visit are Koreatown, Chinatown, Annex, the Beaches, Danforth (Greek town), Junction, Leslieville, and Yorktown – check it. All of the neighborhoods sort of run into each other and blend together.

It’s a city you never knew you wanted to go, but trust me, you really do.

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