Weekend guide · October 23–25, 2026
Things to Do in Winnipeg This Weekend: October 23–25, 2026
Rock shows, hockey matchups, and a market after-party shape a packed Winnipeg weekend with music and sports anchoring each day.
By Weekend Owl · Published October 22, 2026
Winnipeg’s weekend is stacked, especially on Saturday, with music and hockey taking over the city. Friday starts with a rock show at The Park Theatre. Saturday gets busy, anchored by Neighbour Andy at Burton Cummings Theatre, Darcy Oake at Centennial Concert Hall, and the Jets vs. Canadiens Alumni game at Canada Life Centre, all leading into the Alumni Game After-Party at TN Square. Sunday wraps things up with the 2026 Tim Hortons NHL Heritage Classic at Princess Auto Stadium.
Dwayne Gretzky - Canada's Greatest Party Band
If you’re in the mood for a rock night out, Dwayne Gretzky brings their set to The Park Theatre on Friday, October 23 at 8:00 PM. This is a solid pick for anyone wanting to kick off the weekend with live music. The venue’s on Osborne Street, and tickets start from $29.56.
Neighbour Andy
Neighbour Andy is playing a Saturday evening set at Burton Cummings Theatre, starting at 7:30 PM. If you want a classic rock concert experience to anchor your Saturday, this is a good bet. The theatre is on Smith Street and works well for anyone looking to catch live music downtown.
Darcy Oake
Darcy Oake takes the stage at Centennial Concert Hall on Saturday, October 24 at 7:00 PM. This is another rock-focused night, suited for those who like their concerts early and want to catch a show at the concert hall on Main Street. Presented by Live Nation Music.
2026 Tim Hortons NHL Heritage Classic- Canadiens v Jets
The 2026 Tim Hortons NHL Heritage Classic has the Montreal Canadiens facing the Winnipeg Jets at Princess Auto Stadium on Sunday, October 25 at 6:00 PM. If you’re after a big sports outing to close the weekend, this outdoor hockey game should do the trick.
Winnipeg Jets vs. Montreal Canadiens Alumni
On Saturday, October 24, the Winnipeg Jets take on Montreal Canadiens Alumni at Canada Life Centre. The start time hasn’t been announced, but this is the pick for hockey fans wanting to see legends from both teams. The Canada Life Centre is on Portage Avenue.
Alumni Game After-Party | Hargrave Street Market
After the alumni hockey game on Saturday, TN Square hosts the Alumni Game After-Party at Hargrave Street Market, starting at 8:30 PM. If you want to keep the evening going with food and drinks, this is a practical way to wind down your Saturday. Tip: TN Square is a short walk from Canada Life Centre.
A plan for the weekend
Here’s one way to pace your weekend: Start Friday night with Dwayne Gretzky at The Park Theatre. On Saturday, catch Darcy Oake at Centennial Concert Hall at 7:00 PM, then head over to TN Square for the Alumni Game After-Party at 8:30 PM. Sunday evening, wrap things up with the NHL Heritage Classic at Princess Auto Stadium at 6:00 PM. This plan lets you sample both music and hockey without overlapping shows.
How this guide is made: each week we pick one event from each kind of event listed in Winnipeg (music, comedy and theatre, the arts, sports, food and drink, family, community, wellness), favouring named acts and the bigger nights. The write-up is drafted with AI from those listings and nothing else. Times and prices come from the ticket sellers, and plans change, so confirm with the organizer before you go.
Other cities this weekend: Brampton · Buffalo · Calgary · Chicago · Edmonton · Halifax · Hamilton · Las Vegas · Mississauga · Montreal · Nashville · New York · Orange County · Ottawa · Pittsburgh · Salt Lake City · Toronto · Vancouver