The 10 Best Places To Have A Drink On Ossington Avenue

Come take a trip down the Ossington strip
The 10 Best Places To Have A Drink On Ossington Avenue

As you may or may not know, there is no shortage of places to choose from for anyone looking for a cool drink while exploring the west end of the city. Far enough away from the hustle and bustle of the downtown core, but still plenty close to all the action, you'll be able to find yourself a good time if you put your mind to it. But where should you go?

On the bottom end of Ossington Avenue, tucked away between Dundas Street and Queen Street West, is a half kilometre stretch of road positively teeming with trendy shops, hip restaurants and most importantly of all, a metric shit ton of awesome bars. The Ossington strip is perfect for anyone looking to wind back with a quick drink, or two, or maybe even ten depending on your mood. So if you find yourself in the area, and you're looking to have a little bit of fun, you really can't go wrong with this list of local watering holes.

1. The Dakota Tavern

249 Ossington Ave

Take a quick glance over at the sign by the front door that simply reads "Beer, Music, Whisky" and you'll have a pretty good idea what sort of vibe to expect from the Dakota Tavern. This urban hipster answer to the country western saloon is always a honky tonkin' good time. Although, for what sort of clientele to generally expect in this basement bar, think less cowboy boots with wranglers and more trendy hairstyles with skinny jeans.


2. Crooked Star

202 Ossington Ave

We're still not entirely sure what the deal is with that metal sign hanging out front, but what we do know is the inside of the Crooked Star is a small but cozy room with a welcoming atmosphere. Fans of the caesar cocktail will also be happy to hear that the Crooked Star features an array of specialty variations including Jamaican jerk, tandoori, wasabi and ginger and even dijon and capers. These unique takes on the classic caesar aren't advertised anywhere on the wall though, so just ask your friendly bartender to whip one up for you.


Photo Cred - instaho

3. BQM

210 Ossington Ave

BQM stands for Beer & Quality Meats, and is a combination that simply can't be argued with. This speciality burger shoppe is the sister site to the owner's east side location, with the difference being this one is luckily fully licensed! Besides an array of mouth watering hand crafted burgers to choose from, patrons can also select from multiple local craft beers and intoxicating bourbons to wash down the wave of shame that rushes over you after finishing your second deep fried dill pickle hamburger.


4. The Painted Lady

218 Ossington Ave

Look for a red-light lit doorway and a huge sprawling chalkboard of upcoming live music listings to find this unique establishment that bills itself as "The Original Rock'n'Roll, Funk, Glam'n'Soul Music + Burlesque Bar." Maybe it's the shiny rotating disco ball hanging over the stage, the leopard print wallpaper leading to the basement bathroom, or just the multiple gothic themed pictures of skulls and classic pin-up girls lining the wall, but this dimly lit yet brightly coloured bar demands a good time be had by all.


5. La Saucisserie

229 Ossington Ave

Don't let the fancy french name scare you off because this bar is all about having a good time. Besides featuring a whopping 60 different types of beer, many of them of the Ontario craft beer variety, La Saucisserie also serves 20 different varieties of sausage ranging from typical pork to more exotic fare like duck and wild boar. You'll also likely need a sausage or two to fill up your stomach after sampling the Delirium Tremens, which is a golden ale they offer on tap that also just so happens to clock in at a mind numbing 8.5 percent.


6. Reposado

136 Ossington Ave

If you're looking for a drink choice inspired by something a little south of the border then you might as well head on over to the Reposado tequila bar. Boasting a huge selection of premium quality tequilas, not just that awful stuff you blacked out on in first year university, this classy establishment also has a Mexican tapas menu, as well as a pretty awesome back patio hidden away from the outside world.


7. Bellwoods Brewery

124 Ossington Ave

Get here early because on the weekend this place fills up fast, and for a very good reason too. The Bellwoods Brewery brew pub has a huge front patio overlooking the street, a full menu of food available, and serves an array of its very own craft beers brewed on site. Even better, you can hop over next door when you're done and buy a bottle of beer to go at the brewery's retail store. Pro tip: the retail store is open until 11 p.m., so next time you're late getting to the Beer Store or LCBO just march over to the Bellwoods and stock up for the night.


Photo cred - Uber

8. Hawker Bar

164 Ossington Ave

If you've brought along your significant other/next meaningless hookup out for a night on the town, and you're looking to impress while on the Ossington strip, you'll do no better than at Hawker Bar. It seems the owners even encourage patrons to try and impress their dates with a sign posted out front that simply states "Prove That You Love Me And Buy The Next Round." This classy establishment also features a South East Asian inspired food menu, a full cocktail list and has expanded onto the second floor for added space. Next rounds on you.


9. The Ossington

61 Ossington Ave

While the name itself may be lacking in creativity, make no mistake that this trendy hangout is definitely one to look out for as you venture further down Ossington. The front room offers a laid back space perfect for enjoying a drink and a bite of food with your fellow colleagues; however, the back room is where all the action happens, and on certain nights can host events ranging from comedy shows to full on dance parties. Did we also mention there is a stuffed zebra head? Because there is totally a stuffed zebra head.


10. Sweaty Betty's

13 Ossington Ave

Think of Sweaty Betty's as sort of a hipster mecca when it comes to dive bars on Ossington Avenue. With it dark red walls, aging juke box and framed tattoo art Sweaty Betty's is a refreshing no frills answer to typical Toronto extravagance. Even the food menu keeps things simple, with mouth watering options available like a pickle for a $1.00, chips for $1.50, and $3.00 for popcorn if you're looking to go all out. Plus, they even sell packs of smokes! The bar's small front room can fill up pretty fast, but this eccentric hole in the wall actually opens up to a pretty decent patio space out back, so next time you're down by Queen and Ossington stop by and see how the night turns out.