The Toad in the Hole & The Cavern / 112 Osborne St
This multi-level space has been a fixture in Osborne Village for as long as I can remember. Friends gather here for pretty much everything— a quick game of pool, one of the best whiskey sours in the city, a chill night in one of the big booths, or a crazy time at Soul Night downstairs. No one seems to mind that the bathrooms are always breaking or the building (and furniture) are practically prehistoric.
The King's Head Pub / 120 King St
It's the inaugural meeting place for stressed-out Red River College students and the English-style pub spot where business dudes can grab a greasy burger for lunch. With seating areas on three different floors, it's a bit of a maze in there (if you haven't gotten lost trying to find your way back to your seat after six pints of St. James, trust me— you will.) What makes this place so legendary is the people who work there and the photos, memorabilia, and relics that dot the walls.
Yellow Dog Tavern / 386 Donald St
For more than 10 years, the always friendly Yellow Dog has been the place to go before and after concerts at the Garrick or the Burt. Apparently, the Modest Mouse frontman once showed up there after a concert, grabbed his guitar, and jumped onstage to perform into the early hours of the morning for the few dozen people drinking there. HOW COOL IS THAT?
Times Change(d) High And Lonesome Club / 234 Main St
This roots-blues music venue is one of the city's most historically significant buildings (it was built in 1882 by a man who later died in the sinking of the Titanic). As a Winnipegger, it's practically your duty to immerse yourself in the friendly atmosphere and sweet sounds of blues tunes one Friday night.
Le Garage Cafe / 166 Provencher Blvd
A favourite bar for the francophones in the city (or anyone who loves a great plate of poutine, really). Le Garage has been around since 2008 and you can almost always find a local band performing and a crowd of people dancing in front of them if you head there after dark -- especially during Festival Du Voyageur!
Limelite Tavern / 531 St. Mary's Rd
If you've ever made a fool of yourself during a night out, you probably did it at Limelite. No cover charge + cheap drinks + karaoke all night = lots of deleted snap stories the next morning. There's a reason there's practically no photos of this basement bar circulating the web (that, and the notoriously spotty WiFi down there.)
AGIT Karaoke Bar / 201-110 Osborne St
Bar Italia / 737 Corydon Ave
Forget the weather network: the only real way to tell if summer has arrived in Winnipeg is to check the Bar I patio—it's packed from April to October. Pretty sure it's the designated hang out for biker groups, hipsters, lowkey models, and aspiring DJs all at the same time. This place is awesome.
Wee Johnnys / 177 McDermot Ave
This Harry Potter-esque Irish pub is under the stairs of Johhny G's (also a Winnipeg staple with v. delicious shoestring fries). It's a favourite place for local performers, and you'll probably forget you're still in Winnipeg when you enter it (especially after a few pints of Guinness.)
Fame Nightclub / 279 Garry St
Fame opened in 2011 after a few other GLBTTQ* spots closed down in the city. It's one of the best spots if you want to really, really want to dance and not have 5843902 straight dudes judge you.
ANAF Club 60 / 433 River Ave
Don't ask me how an army, navy, and air force club became popular with the young crowd, but here we are (blame it on the hipsters, probably.) The ANAF Club is the opposite of flashy and it's the best place to grab a quick beer with your buds outside of your own living room.
Garbonzo’s Pizza Pub / 471 Balmoral St
Thank god for Garbs opening in 2012, otherwise U of W students would have nowhere fun to study (the library? Where's that?). This is the best place to watch an election, debate, or hang out while you skip your 1000 level English course.
Flea Whiskey's / 601 Erin St