Hell Yeah Comedy
2026-07-12 19:00 - 21:00, 2026-07-19 19:00 - 21:00, 2026-07-26 19:00 - 21:00, 2026-08-09 19:00 - 21:00, 2026-08-16 19:00 - 21:00, 2026-08-23 19:00 - 21:00, 2026-08-30 19:30 - 21:00 (America/Winnipeg) | Devil May Care Brewing, 155-A Fort St, Winnipeg, MB, R3C1C8, Canada
If you’re ready for laughs on tap, let me hear a HELL YEAH
Every Sunday, we’ve got open mic comedy hosted by local funny-guy Jeffrey Gobeil. It’s free to get in on the fun, so pop on by and laugh away the Sunday Scaries with us in the taproom.
Registration at 6:00, and the jokes start flyin’ at 7:00.

Watch Party: Semi-Final #1
2026-07-14 14:00 - 17:00 | Devil May Care Brewing, 155-A Fort St, Winnipeg, MB, R3C1C8, Canada
More soccer action, live in the taproom 🌎🏆⚽
Catch the game on the projector or any of the taproom screens. Sound on so you can sing along with the crowd!

Pub Trivia
2026-07-14 19:00 - 21:00, 2026-07-21 19:00 - 21:00, 2026-07-28 19:00 - 21:00, 2026-08-11 19:00 - 21:00, 2026-08-18 19:00 - 21:00, 2026-08-25 19:00 - 21:00 | Devil May Care Brewing, 155-A Fort St, Winnipeg, MB, R3C1C8, Canada
Every Tuesday is Pub Trivia in the taproom!
The topics are varied. The questions are tough. The banter is exceptional. Bragging rights and gift cards are on the line.
It’s FREE TO PLAY, so just turn up and get ready to flex that cranium! Up to 6 players per team.
Questions start at 7:00!

Watch Party: Semi-Final #2
2026-07-15 16:00 - 19:00 | Devil May Care Brewing, 155-A Fort St, Winnipeg, MB, R3C1C8, Canada

Music Bingo
2026-07-16 19:30 - 22:30 | Devil May Care Brewing, 155-A Fort St, Winnipeg, MB, R3C1C8, Canada
Every other week, we play Music Bingo in the taproom!
What’s Music Bingo, you ask? We give you a card and play some songs. Mark off squares as new songs come up, and shout BINGO when you make the pattern of the game. So it’s Bingo… but with music!
It’s free to play, and there’s multiple chances to win prizes!

Watch Party: Third Place
2026-07-18 16:00 - 19:00 | Devil May Care Brewing, 155-A Fort St, Winnipeg, MB, R3C1C8, Canada

Watch Party: The Final
2026-07-19 14:00 - 17:00 | Devil May Care Brewing, 155-A Fort St, Winnipeg, MB, R3C1C8, Canada

Settlers of Winnipeg
2026-07-25 13:00 - 16:00 | Devil May Care Brewing, 155-A Fort St, Winnipeg, MB, R3C1C8, Canada
Join the Settlers of Winnipeg for an afternoon of casual Catan in the taproom
All skills levels are welcome. If you’ve never played, come and learn.
Make sure to follow @settlersofwinnipeg on Instagram or email settlersofwpg@gmail.com for more info!

Name That Tune
2026-07-30 19:30 - 21:30 | Devil May Care Brewing, 155-A Fort St, Winnipeg, MB, R3C1C8, Canada
Ever wish that trivia nights were 100% music rounds?
Join us for an all-audio music trivia night in the style of NAME THAT TUNE. We’ll play a bunch of songs, and you give us the song and artist. Sounds simple, right?
We’ll be running through one decade per round, from the 1960’s all the way up to the 2010’s.
Up to 6 players are allowed per team. There are 6 rounds covering 6 decades of music. You may want to build your team around that. Just sayin’…
There’s a sweet prize for the winners, and maybe some bonuses along the way!
BOOK YOUR SEAT HERE

Devil May Chair - A Chair-ity Variety Show
2026-08-02 19:00 - 21:00 | Devil May Care Brewing, 155-A Fort St, Winnipeg, MB, R3C1C8, Canada
Join host Myles A. Taylor and a fantastic lineup of comedy and music as they come together to raise money for Manitoba Possible and celebrate his birthday!
Show | 7-9 PM
Free admission; donate during the event or online.

Johnny Bolo - Live In Concert
2026-08-08 19:00 - 21:00 | Devil May Care Brewing, 155-A Fort St, Winnipeg, MB, R3C1C8, Canada
From Canada’s Okanagan Valley, solo alt-country singer-songwriter Johnny Bolo has been a presence in the Western Canada music scene for 20+ years. Touring Canada & Europe, from festivals to dive bars, Johnny brings his entertaining “Blue Rodeo meets Jimmy Buffett” sound,engaging audiences with soaring vocals & driving guitar work.
Born in Sudbury Ontario, son of a hard rock miner, raised on the wide plains of Saskatchewan, Johnny Bolo (JB) delivers smiles, energy, connection & Joy! Outlaws & rebels, lovers & dreamers populate his songs, with an authenticity born of his travels & travails. JB brings you stories of the road, trains, & freedom.
www.JohnnyBolo.com
Show | 7-9 PM
Tix | $10 @ door + pay what you can

Improv In The Taproom
2026-08-12 19:00 - 21:00 | Devil May Care Brewing, 155-A Fort St, Winnipeg, MB, R3C1C8, Canada
We’ve got an interactive open improv experience for you in our taproom, hosted by Alyssa Bird and Jeff Gobeil!
Join in one of the short-form games, spin the wheel, and jam with fellow improvers. Open to all levels of experience and skill. If you’re a first-timer or even just improv-curious – this is a great night to try it out!
Not interested in taking part, but still love to watch improv? Great! There’s lots of room for spectators too.
Sign up at 7pm, the wheel spins at 7:30!

Name That Tune 3
2026-08-20 19:30 - 21:30 | MB

CBC and The Tragically Hip present ‘The Tragically Hip: A National Celebration
2026-08-22 19:00 - 22:30 | Devil May Care Brewing, 155-A Fort St, Winnipeg, MB, R3C1C8, Canada
Join us on August 22, 2026, to watch CBC’s 10th anniversary re-broadcast of “The Tragically Hip: A National Celebration” at 7 p.m. local time on CBC TV, CBC Radio, CBC Music’s YouTube page, and CBC Gem. it’s free, and it will be cranked loud!

Movie Trivia
2026-08-27 19:30 - 21:30 | Devil May Care Brewing, 155-A Fort St, Winnipeg, MB, R3C1C8, Canada
“What’s the most you ever lost on a trivia question?” -Anton Chigurh… probably.
Join your host, Gustavo as he returns for his trivia night sequel: Trivia Night 2: Quiz Harder!
It’s $10 to play.
Prizes for winners (and some mini-games to boot!)
Teams of max 6. 7:30 start.
Get tickets here.

Must Be Nice - Indigenous Comedy Night 1
2026-08-28 19:00 - 21:30 | MB
The Must Be Nice Indigenous Comedy Festival is coming to Winnipeg! Two nights. One stage. Some of the funniest Indigenous comedians from across Canada. August 28 & 29, Devil May Care Brewery, 155-A Fort St., Winnipeg. Featuring headliners: Friday: Jeff Gobeil & Nova Fox Saturday: Sherry McKay & Stephen Meechas Hosted by Arsan Buffin, with an incredible lineup of Indigenous comics bringing stand-up, storytelling, and unforgettable laughs all weekend long. $20 per night; $40 Festival Pass; 2-for-1 tickets available. Doors: 6:00 PM; Show: 7:00 PM. Grab your tickets through the QR code and come celebrate Indigenous comedy with us!

Cribbage Tournament
2026-08-29 13:00 - 16:00 | Devil May Care Brewing, 155-A Fort St, Winnipeg, MB, R3C1C8, Canada
Our monthly Saturday afternoon cribbage is back!
We love cribbage around here and the community that it creates. Casual vibes with a round-robin no-knockout format. Every player is guaranteed six games.
It’s free to play – just show up, sign in, and try to skunk your opponent.
Register by 1:00 PM
Feel free to bring a board if you have one you like to use. We have some, but more are always welcome.

Must Be Nice - Indigenous Comedy Night 2
2026-08-29 19:00 - 21:30 | MB
The Must Be Nice Indigenous Comedy Festival is coming to Winnipeg! Two nights. One stage. Some of the funniest Indigenous comedians from across Canada. August 28 & 29, Devil May Care Brewery, 155-A Fort St., Winnipeg. Featuring headliners: Friday: Jeff Gobeil & Nova Fox; Saturday: Sherry McKay & Stephen Meechas. Hosted by Arsan Buffin, with an incredible lineup of Indigenous comics bringing stand-up, storytelling, and unforgettable laughs all weekend long. $20 per night; $40 Festival Pass; 2-for-1 tickets available. Doors: 6:00 PM; Show: 7:00 PM. Grab your tickets through the QR code and come celebrate Indigenous comedy with us!

Pop-Up Record Fair
2026-09-13 13:00 - 16:00 | Devil May Care Brewing, 155-A Fort St, Winnipeg, MB, R3C1C8, Canada
It’s the return of our Pop-Up Record Fair at DMC!
Sunday, September 13 from 1- 4 p.m., come shop with a variety of vendors selling a wide array of vinyl and other collectibles, right here in the taproom.
Free admission, delicious beer on tap, and some great DJs spinning tunes for the afternoon!
For vendors: email iwillfreshyou@gmail.com to book a table.
