What to do this weekend in Winnipeg, MB (18-19 July 2026)
Assiniboine Park is about to become the funniest patch of grass in Manitoba, and honestly, that's reason enough to clear your Saturday. Jim Gaffigan headlines the Great Outdoors Comedy Festival alongside John Crist and Ryan Hamilton, and if you'd rather stretch that laughter into the afternoon, Jeff Arcuri is also on the lineup with his own set the same day. This isn't some one-off gig — it's a full-blown festival takeover, and outdoor comedy shows like this don't roll through Winnipeg, MB every weekend.
If sports get your blood pumping more than punchlines, Princess Auto Stadium is hosting the World Rugby Nations Cup 2026, with Canada and Zimbabwe going head-to-head alongside other international matchups. It's the kind of high-stakes, high-energy weekend that turns casual fans into diehards by the final whistle — and tickets for events like this tend to disappear fast once word gets out.
Prefer your Saturday night a little looser and louder? Grab a mic at Sidestage Karaoke and turn yourself into the weekend's unexpected headliner. Between the comedy tents, the rugby pitch, and the karaoke stage, Winnipeg's lineup of shows this weekend is stacked with options that don't require picking just one mood to commit to.
Scroll down — your perfect Winnipeg weekend is already booked, you just don't know it yet.
A karaoke night at Sidestage in Winnipeg, hosted as always by Matt McLean. Doors and sign-up from 8 PM, singing from 8:30 PM until late. An all-ages event (kids get priority to sing), free…
Rock matinee with Saints & Rogues, Graffiti Parks and Electric Wine at Sidestage in Winnipeg. The Osborne Street room gathers three local bands for an afternoon of live music. All-ages…
Winnipeg edition of the Great Outdoors Comedy Festival at Assiniboine Park. A bill of North American comedians performing outdoors in the city's large urban park: stand-up under the trees,…
An outdoor stand-up festival touring Western Canada — Calgary, Edmonton, Winnipeg, Vancouver. North-American headliners on a big outdoor stage, single-day or weekend pass options. Picnic…
American stand-up Jeff Arcuri, known for his viral crowd-work clips and the special The Full Arcuri, takes the Saturday afternoon slot at Winnipeg's Assiniboine Park for the Great Outdoors…
Saturday evening of the Great Outdoors Comedy Festival at Winnipeg's Assiniboine Park. Aziz Ansari (Master of None, Parks & Rec), Pete Davidson (SNL, The King of Staten Island) and New York…
Friday-evening Great Outdoors Comedy Festival show at Winnipeg's Assiniboine Park. A US stand-up lineup: Jim Gaffigan (veteran, multiple Grammy nominee, family and food observations), John…
A rugby doubleheader from the Nations Cup 2026 at Winnipeg's Princess Auto Stadium: Tonga versus Portugal, then Canada versus Zimbabwe. Two international rugby union matches on the same…
The Winnipeg Sea Bears host the Montreal Alliance at Canada Life Centre in the Canadian Elite Basketball League. The Manitoba side, with former MVPs Xavier Moon and Teddy Allen on the 2026…
Inaugural edition of the World Rugby Nations Cup at Princess Auto Stadium in Winnipeg, the city's first international men's rugby match in 33 years. Tonga, a classic Pacific Island…
Winnipeg leg of the 2026 World Rugby Nations Cup at Princess Auto Stadium in Winnipeg. This annual international competition brings together emerging and established national sides for…
Canadian Elite Basketball League (CEBL) game: the Winnipeg Sea Bears host Montreal Alliance at Canada Life Centre. Summer season, Target Score finish, family-friendly arena.
The Winnipeg stop of the Great Outdoors Comedy Festival takes place at Assiniboine Park on July 19, 2026, headlined by Matt Rife. The American comedian, who went viral for his TikTok…
The Winnipeg stop of the Great Outdoors Comedy Festival takes over Assiniboine Park, with American comedian Jeff Arcuri headlining. Gone viral thanks to his crowd-work clips shared on…
Winnipeg edition of the Great Outdoors Comedy Festival at Assiniboine Park. A bill of North American comedians performing outdoors in the city's large urban park: stand-up under the trees,…
Winnipeg edition of the Great Outdoors Comedy Festival at Assiniboine Park. A bill of North American comedians performing outdoors in the city's large urban park: stand-up under the trees,…
