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19 Best Bars and Restaurants in Ossington Village

Best Bars and Restaurants in Ossington Village
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Ossington Village has some great hidden gems of must-try restaurants and bars that you might not have visited yet. Whether you’ve explored it all or are just starting, we’ve got you covered with this list of spots to keep you going back for more.

Bar Bowie

Address: 180R Ossington Ave, Toronto, ON M6J 2Z7, Canada

Operating hours: 

  • Opens daily from 6 PM to 2 AM

Bar Bowie offers fantastic cocktails and serves food at the bar. Nestled under a laundromat, it stands out as one of Toronto’s top new bars.

No need to call or make reservations – even their IG discourages DMs. Just go right to the bar and enjoy the night out with your choice of cocktail – or two – in your hand.

Pro Tip:
We don’t know about you but we love their eclectic choices like Espresso Martini, the Paloma, and the Lychee Martini.

Bar Shozan

Website: https://www.barshozan.com/ 

Address: 164 Ossington Ave, Toronto, ON M6J 2Z7, Canada

Contact details: (647) 478-6164

Operating hours: 

  • Wednesday to Thursday: 12:30 PM – 4 PM, 5 PM – 10 PM
  • Friday to Saturday: 12:30 PM – 4 PM, 5 PM – 12 AM
  • Sunday: 12:30 PM – 4 PM, 5 PM – 9:30 PM 

Bar Shozan offers Japanese delicious dishes with a modern twist to keep things interesting. They focus on Japanese tapas, but you can also enjoy sushi, ramen, and the great and filling teishoku set meals. 

And, of course, they have a great selection of sakes, wines, beers, and cocktails. You can choose to spend a great night here and head home – or continue the revelry at nearby bars on Ossington.

Pro Tip:
It’s hard to pick from their Hamachi Crudo, Crispy Shrimp & Corn Skewers, Squid Tentacle Tempura, Pork Belly Yakiton, and Kara-Age Fried Chicken – so we suggest bringing your friends for the meals and for the sake!

Bar Habana

Website: https://www.barhabana.ca/ 

Address: 92 Ossington Ave, Toronto, ON M6J 2Z4, Canada

Contact details: (416) 

Operating hours: 

  • Sunday to Tuesday: Closed
  • Wednesday to Saturday: 6 PM – 1 AM

La Cubana, led by chef Corinna Mozo and co-owner Pablo, has been bringing fresh twists to classic Cuban flavors since 2007. The menu offers delicious small bites like empanadas, yuca fries, and Cuban corn with queso fresco. 

Enjoy specialty cocktails inspired by Havana’s vibrant bar scene. Bar Habana welcomes you into the Latin American culinary experience, offering pressed sandwiches, meats with rice and beans, all in a nostalgic Cuban diner setting.

Pro Tip:
Try some of the Old Baracoa or Como La Flor to go with their Roasted Chiote Chicken and Honey Glazed Pork Belly.

Paris Paris

Website: https://www.parisparis.ca/ 

Address: 146 Ossington Ave, Toronto, ON M6J 2Z5, Canada

Contact details: (437) 983-8774

Operating hours: 

  • Sunday to Wednesday: 12 PM – 1 AM
  • Thursday to Saturday: 12 PM – 2 AM

Visit Paris Paris on Ossington for a laid-back wine bar experience. With an unassuming vibe, they have a wide selection of wines by the glass and a snack menu with international flavors. 

Whether it’s winter or summer, the inviting space, once an auto garage, offers a cozy atmosphere. Enjoy a seasonal, contemporary menu with bistro-inspired dishes, and explore their excellent options in wine, spirits, and cocktails. 

Pro Tip:
Take time to try the Lobster Spaghetti and then maybe share Mousse au Chocolat for Two for that elegant and filling meal – of course with some of their wines, in an outdoor seating option if you want.

Bar Banane

Website: https://www.barbanane.ca/ 

Address: 227A Ossington Ave, Toronto, ON M6J 2Z8, Canada

Contact details: (647) 693-1103

Operating hours: 

  • Closed on Sunday to Monday
  • Tuesday to Thursday: 6 PM – 12 AM
  • Friday to Saturday: 6 PM – 2 AM

Bar Banane, situated above La Banane, is a cocktail bar offering French-inspired snacks, drinks, and soufflés. Keep in mind that Bar Banane and Restaurant La Banane are distinct places, and reservations need to be made separately. 

They serve fantastic cocktails and food at the bar, accept reservations, and also leave room for walk-in guests. Be sure to take a sample of their eclectic mix of snacks with at least one drink on the side.

Pro Tip:
We suggest their Nova Scotia Lobster Croustade, but you can also try the Foie Gras Brûlée for a bit of interest along with Daydream Nation or Carbarita for cocktails.

UNION

Website: https://union72.ca/ 

Address: 72 Ossington Ave, Toronto, ON M6J 2Y7, Canada

Contact details: (416) 850-0093

Operating hours: 

  • Monday: 5 PM – 10 PM
  • Tuesday to Friday: 11:30 AM – 10 PM
  • Saturday to Sunday: 10 AM – 3 PM, 5 PM – 10 PM

Enjoy tasty French dishes in a cozy Parisian bistro with a Canadian twist. They feature a weekly menu with classics made from fresh, local ingredients – perfect if you’re into healthy eating to offset your alcohol intake! 

Plus, you can dine outdoors for a fantastic fresh-air experience while checking out the pedestrians. The daily menu updates ensure you savor the best of local and seasonal flavors – so you might want to visit to check on their specials for the day.

Pro Tip:
Take your pick from the alcoholic and non-alcoholic drinks to go with your specials of the day.

Downtown Winery

Website: https://downtownwineryto.com/ 

Address: 30 Ossington Ave, Toronto, ON M6J 2Y7, Canada

Contact details: (416) 537-0416

Operating hours: 

  • Closed on Monday
  • Tuesday to Wednesday: 12 PM – 8 PM
  • Thursday to Saturday: 12 PM – 10 PM
  • Sunday: 12 PM – 7 PM

Downtown Winery is a family-run wine bar and bottle shop with tasty snacks and a patio. The best part is the happy hour from 2 to 6 PM, where you can get 5-ounce glasses at great prices, including some great choices from their own wines. 

They offer good, affordable wine and free corn nuts for everyone. The seating area might be a bit limited, but if you come at the right time, it’s all good. It’s a unique and exciting city leisure concept – highly recommended for wine connoisseurs.

Pro Tip:
We have a preference for rosé, but their extensive lists of reds and whites just makes us visit quite often!

Bar Koukla

Website: https://mamakas.ca/bar-koukla/ 

Address: 88 Ossington Ave Unit 2, Toronto, ON M6J 2Z4, Canada

Contact details: (416) 901-7899

Operating hours: 

  • Closed on Monday
  • Tuesday to Friday: 5 PM – 12 AM
  • Saturday: 11 AM – 12 AM
  • Sunday: 11 AM – 4 PM, 5 PM – 2 AM

Bar Koukla is all about being the right place for the right people. This trendy spot, inspired by Athenian snack bars, offers small dishes, seafood, cocktails, and wines delectable enough to keep you coming back for more. 

Service options include outdoor seating, fantastic cocktails, and vegetarian dishes. It’s an Aegean-inspired meze and wine bar open late for night owls – so you might want to swoop in before or after your nightly haunts!

Pro Tip:
If you want your weekends to go longer, go for the Weekend brunch from 11 AM to 4 PM.

Man of Kent

Website: https://www.manofkentpub.com/ 

Address: 202 Ossington Ave, Toronto, ON M6J 2Z7, Canada

Contact details: (647) 231-2312

Operating hours: 

  • Opens daily from 2 PM – 2 AM

Man of Kent feels like a classic English pub, offering affordable cold pints, mushy peas, and tasty pies. The inside is cozy, with dim lighting, and it avoids the usual colonial or British royal decor seen in other pubs. 

The tartar sauce is fantastic, and the food goes beyond expectations, providing good value for the price. The outdoor seating on Ossington is among the best – especially if you’re into good food, good company, and a bit of people-watching.

Pro Tip:
We were lucky to have the Roasted Sirloin available though you can always go with the classic Cornish Pasty and some of that sinfully Sticky Toffee Pudding.

Pastiche

Website: https://www.pastichenoshery.com/ 

Address: 59 Ossington Ave, Toronto, ON M6J 2Y9, Canada

Contact details: (416) 533-8018

Operating hours: 

  • Closed from Sunday to Tuesday
  • Wednesday to Thursday: 5 PM – 1 AM
  • Friday to Saturday: 5 PM – 2 AM

Pastiche offers diverse sharing plates and vibrant cocktails in a cozy, well-lit setting though they serve them at the bar too. If you’re up for a late-night adventure, Pastiche is the place to be. 

Their cocktail menu may be small, but they can create something special just for you. And don’t forget to grab a bite with your choice of cocktail – think of it as a way to keep your senses happy and buzzed!

Pro Tip:
We’re carnivores, so we recommend the Farm – six meat-based dishes from their menu. Keep in mind that the offerings may change based on what’s available. There’s also the Garden – your vegetarian choice.

The 222 Bar

Address: 222 Ossington Ave, Toronto, ON M6J 2Z9, Canada

Operating hours: 

  • Monday to Thursday: 5 PM – 2 AM
  • Friday to Sunday: 3 PM – 2 AM

222 is a cozy bar with soft lighting, offering fancy cocktails in a setting that feels like an ’80s hotel lobby. It’s a fresh project by the same folks who own popular spots in Toronto, such as 3-Speed and The Communist’s Daughter.

The place has quite a history – if you’re interested in the place’s previous owners. Before becoming 222, it used to be The Grow Op, a juice bar, and even earlier, it was a Portuguese fish shop.

Pro Tip:
The Bloody Marley takes a hemp inspiration on the classic Bloody Mary, but you can try the Penicillin for a healthy yet alcoholic kick!

Season Six

Address: 188 Ossington Ave, Toronto, ON M6J 2Z7, Canada

Contact details: (416) 537-7276

Operating hours: 

  • Monday to Thursday: 12 PM – 10 PM
  • Friday to Saturday: 12 PM – 2 AM
  • Sunday: 12 PM – 9 PM

This place serves healthy bowls and salads along with wine and customizable dishes. They offer outdoor seating and make excellent cocktails – so order to your booze-loving heart’s desire.

If you want gluten-free food, they have a whole menu just for that. It’s a full-service restaurant, a bar for drinks, and also a fast-service kiosk – making everything easy, fun, and delicious!

Pro Tip:
We have several favorites: Roasted Chicken Leg, Beef Brisket Bourguignon with Creamy Pinned Purée and Roasted Spring Heirloom Carrots, and the Flourless Chocolate Torte

Sweaty Betty’s

Website: https://sweatybettysbar.com/ 

Address: 13 Ossington Ave, Toronto, ON M6J 2Y8, Canada

Contact details: (416) 535-6861

Operating hours: 

  • Monday to Friday 3 PM – 2 AM
  • Saturday to Sunday 3 PM – 2 AM

Sweaty Betty’s, a dive bar in Toronto for more than 20 years, is known for its crowds and fitting name. It’s currently run by May Brand, who’s been in charge for almost two decades after working at nearby places like the Gladstone and Beaver.

The bar is comfy and straightforward, with various furniture, a relaxed back room, and a nice patio. You can bring outside food, sit outdoors, and walk in without reservations.

Pro Tip:
What’s not to love? Good food, great drinks, LGBTQ+ friendly, chill people with the back patio warm and sheltered for some fresh air and people watching.

Baby Huey

Address: 110 Ossington Ave, Toronto, ON M6J 2Z4, Canada

Contact details: (647) 352-0870

Operating hours: 

  • Closed on Tuesday to Friday
  • Friday to Monday: 9 PM – 2 AM

Baby Huey is a lively spot with DJ sets and drink specials, drawing a spirited crowd. The central bar separates the space, and at the back, there’s a dance floor with a DJ booth that adds to the unique decor like the graffiti directions to the washrooms. 

The venue, formerly Rock Lobster, is spacious with high tables, a chalkboard, vintage posters, and quirky chandeliers. While Baby Huey doesn’t serve food, they provide numbers for nearby eateries like Pizza Pizza and KFC if you fancy a bite.

Pro Tip:
Order some chicken wings, cauliflower french fries, and sausage rolls to pair with the cocktail or drink of your choice.

The Dakota Tavern

Website: https://www.dakotatavern.ca/ 

Address: 249 Ossington Ave, Toronto, ON M6J 3A1, Canada

Contact details: (416) 850-4579

Operating hours: 

  • Wednesday: 6:30 PM – 6 AM
  • Thursday to Tuesday: 6:30 PM – 2 AM

It’s a rustic basement bar offering Southern-style pub food and hosting nightly live music performances – including several Canadian music legends. You can’t reserve a spot here, but you can enjoy live acts and dancing. 

The Dakota Tavern, also known as the Dakota, may have only opened in 2006, but it feels like it’s been around longer. Maybe it’s the folk and honky tonk music or the cozy basement setting. 

Pro Tip:
If you’re going cashless – use your credit since these are the only 2 options available. Other than that, enjoy some honky tonk music with your beer!

The Gift Shop

Website: https://www.freehouse.co/locations/gift-shop 

Address: 89-B Ossington Ave, Toronto, ON M6J 2Z2, Canada

Contact details: (416) 546-5432

Operating hours: 

  • Closed on Monday
  • Tuesday to Wednesday: 7 PM – 12 AM
  • Thursday to Saturday: 7 PM – 1 AM
  • Sunday: 7 PM – 12 AM

The Gift Shop is the bar located behind Barber & Co., a men’s parlour on Lower Ossington. As Ossington changes for the better, the bar at the back of this barber shop reflects the idea that we can all be artists in our own way – with hair and drinks.

You can also have a beer or cocktail while getting your hair done. For the complete experience, it’s best to visit after 8 PM from Wednesday to Sunday – where you get to unwind from a long day with some friends or even by yourself.

Pro Tip:
For a delightful visit to the sweet spot, try Willy Wonka’s Chocolate Factory or go right to the point with The Art of the Dill.

Reposado

Website: https://www.reposadobar.ca/ 

Address: 136 Ossington Ave, Toronto, ON M6J 1R5, Canada

Contact details: (416) 532-6474

Operating hours: 

  • Closed on Sunday
  • Monday to Saturday: 6 PM – 1:30 AM

Reposado on Ossington is a stylish, dimly lit spot known for its top-shelf tequilas, Mexican tapas, and live music. You won’t find cliché Mexican decorations here – it’s a more intimate and refined spot with exposed brick walls and perfect mood lighting. 

The ambiance is cozy, with bar stools and a few four-seater tables. Live jazz and swing performances happen on Thursdays and Fridays, while Wednesdays feature live music, and most other nights have DJs. 

Pro Tip:
To complement your drinks, there’s a small selection of tapas, including tequila and chorizo, cured salmon, and chips and dip. Outdoor seating is available, and outside food is allowed.

Painted Lady

Website: https://thepaintedlady.ca/ 

Address: 218 Ossington Ave, Toronto, ON M6J 2Z9, Canada

Contact details: (647) 213-5239

Operating hours: 

  • Monday to Thursday: 6 PM – 3 AM
  • Friday to Sunday: 2 PM – 3 AM 

The Painted Lady offers burlesque shows and DJ entertainment in a lively saloon with a beautiful mahogany bar, serving craft beer and creative snacks. With outdoor seating, fantastic cocktails, and live music, it captures the pre-Katrina New Orleans vibe.

The menu features Korean kabobs, pulled pork with original BBQ sauce, and white trash nachos, which surprisingly works with homemade chili, Fritos, and Cheez Whiz. The bar offers twelve taps of Canadian craft beer, staples, and obscure Euro imports. 

Pro Tip:
Get the namesake the Painted Pink Lady – a decadent mix of gin, brandy, lemon juice, and frothed egg.

I Deal Coffee & Wine

Website: https://idealcoffee.ca/ 

Address: 162 Ossington Ave, Toronto, ON M6J 2Z7, Canada 

Contact details: (416) 364-7700

Operating hours: 

  • Monday: 9 AM – 5 PM
  • Tuesday to Thursday: 7:30 AM – 7 PM
  • Friday to Saturday: 7:30 AM – 11 PM
  • Sunday: 7:30 AM  – 7 PM

I Deal Coffee & Wine is just that – a playful pun on the perfect place that deals with coffee and wine. This coffee roaster and cafe offers local bakery goodies in a cozy space with pews and vintage chairs. 

Coffee and wine are Friday essentials for any Canadian, so we might as well grab them from one spot. You can grab your coffee starting at 7 am and swing by later for a nice glass of wine in the evening – rounding up your day perfectly.

Pro Tip:
After drinking coffee before or after your wine, you might want to grab their bags of coffee ranging from light to dark blends – or just subscribe to their monthly bags!