Eating Through TO

Neighbourhood Guide: Ossington Strip

Our office is located at Queen and Ossington, thus we spend an almost unhealthy amount of time and money in this neighbourhood. We only felt it appropriate to be our first guide released for 2019.  A little bit hipster, a little bit fancy, and chocked full of character, your first time on the Ossington Strip is surely one you won’t forget!

Check out our video to get the vibe, and click the links below to find out more about each spot:


Pilot coffee

A long-time favourite in the city but new and improved in the hood. The interior is sleek and sexy with all the bells and whistles. Espresso machines built into the counter, digital menu boards, and some mean avocado toast, this modern cafe will draw you in and have you stay a while.

Despite being one of several locations now in downtown Toronto. Jimmy’s has kept an authentic and down-to-earth vibe. Mis-matched furniture and rustic design make you feel at home in the way only a good coffee shop can. Staff is friendly, fast, and consistent. A perfect spot to become your daily. 

Food + Drink

First established on Roncy (or Roncesvalles) La Cubana adds to the diversity of Ossington. Serving up plates with fried plantain, rice n’ beans, and spicy red cabbage, you won’t be left hungry. Hearty sandwiches, good coffee, and their own house draught beers make this one of our habitual lunch spots. That being said, it can just as easy serve as your casual dinner destination. 


A new-comer to the strip, but they came with style and finesse. The room transports you to the Mediterranean with Moroccan woodwork and colourful tiles. To start, their cocktail list is on point and both food and drink incorporate spices such as saffron, cardamom, and rosewater. We suggest the Battle of Algiers, Saffron Rice, and the Fried Brussel Leaves as well. 

A Korean-inspired dive bar with dangerously delicious food at fair prices. Try favourites such as the squash poutine with kimchee, ‘The Loosie’ and the Bulgogi Cheesesteak. Rotating taps and fun cocktails make it a great watering hole as well.

Superpoint is a favourite among locals. Offering pizza-by-the-slice and takeaway during the afternoon. During the evening it opens up in the back and has a larger menu and drink offering. We love the Cream of Mushroom and the Genoa Salami with spicy honey. 


Our favourite ice cream in Toronto. Get creative while constructing your own gourmet ice cream sandwiches. Combine interesting flavours of ice cream to nestle between cookies, cream puffs, macarons, or Hong Kong waffles. The Bees Knees is a hit with salted honey and chamomile tea. During the summer months there always tends to be a line, but that just attests to the quality.

Hidden away in an apparel shop with some of the city’s most eye-catching milkshakes and hot chocolate. Whether it be s’mores, birthday cake, or cotton candy, get your phone ready to snap some instagrammable pics! (located inside Peace Collective)


This charming housewares shop opened up last year and has an eclectic mix of items to spice up your apartment. Art prints, bags, and accessories are also on offer. You may find that it’s a perfect place to buy a gift, even if that gift is for yourself.


An apparel shop which gave Torontonians what they needed to start showing some pride. Shirts have prints such as ‘Toronto Vs. Everyone’, ‘Home is Toronto’ and ‘Home is Canada’. The clothes and accessories make awesome souvenirs for travellers and are great for locals who want to stop apologizing for everything. (Sorry.)


The main concept behind Crywolf is producing limited edition, collectible and affordable graphic tees, clothing and accessories. All of Crywolf’s designs are based on co-owners Rose and Stephanie’s drawings which they collaborate on. Don’t forget to hug the adorable mascot outside the front door. 

Hidden away in an apparel shop with some of the city’s most eye-catching milkshakes and hot chocolate. Whether it be s’mores, birthday cake, or cotton candy, get your phone ready to snap some instagrammable pics! (located inside Peace Collective)

Beer + Nightlife

One of the first craft breweries in Toronto, and still debatably the crown jewel of the city’s brewing scene. You can purchase a diverse range of bottles from their bottle shop from 11am-11pm. We are major fans of their Jelly King series. Once the bar opens you can grab a drink, relax, and order some shareables like the herbed fries, house-made pickles + ferments, or the duck rilette.

Barber shop by day, secret cocktail bar by night. Look for the Barber + Co. sign, walk in past the barber’s chairs to a back room. There you will see a cozy bar with fun menus that look like a retro magazine. Flip through, or ask the bartender to make you something of his own creation. The bar opens at 8pm Tuesday thru Sunday. 


Places of Interest

A small theatre specializing in musicals. It’s a great venue to start your evening. Have a few drinks, take in a show, and then grab dinner on the strip. Tickets are not too expensive, but may sell out quickly. 

lower ossington theatre

A few blocks away from Ossington lies Trinity Bellwoods, which is hands down the best park in the city. All summer you will find droves of people laughing, playing games and partaking in picnics. Enjoy pop-up markets and music, as well the food trucks which park along Queen Street by the park’s entrance. It is the heart of the neighbourhood on a warm day.

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