WPG Pennant Weekly

Hiya, Winnipeg! Welcome to another edition of the WPG Pennant and a look at the things that make this city tick.

In today’s edition:

Let’s get to it.

— Ryan Bowman

🌡️ High 8 Low -1 ⛅ Mix of sun and cloud

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🌡️ High 11 Low 2 ☀️ Mostly sunny

Last week, local developers took a long-awaited first step toward revitalizing the city’s core —one that holds hope for new life, energy, and momentum for Winnipeg as a whole.

Construction offically began at Portage Place, resulting in plenty of demolition and a huge hole where the mall’s atrium once stood. The local landmark, which has occupied three city blocks since opening to plenty of fanfare in 1987, has been on a downward spiral for decades and was sold to True North Real Estate Development in December 2024.

True North’s $650-million undertaking includes plans for a 265,000-square-foot health centre alongside affordable housing, several greenspaces, retail and more. The project is expected to be complete by 2028.

As for the iconic clock, originally installed in Winnipeg’s old City Hall building in 1903 — it’s currently looking for a new home.

Stage set for Grey Cup Halftime Show 🎤

The CFL announced last week that mgk, formerly known as Machine Gun Kelly, would headline Winnipeg’s Grey Cup halftime show on Nov. 16.

Best known for his 2020 album “Tickets to My Downfall” (and/or his very public relationship with actress Megan Fox), mgk will join an entertainment lineup that also includes Our Lady Peace, who will perform before the game, and Manitoba’s own Catie St. Germain, who will sing the national anthem.

Love him or hate him (or have no idea who he is), mgk is a somewhat surprising choice for the CFL, which has desperately been trying to grow its brand and attract younger fans. We’ll have to wait and see if his performance can top last year’s Jonas Brothers Grey Cup halftime show, which drew an average audience of 4.25 million viewers.

A whole lotta laugh 😂

Speaking of headliners, Matt Rife will be the main draw at next year’s edition of the Great Outdoors Comedy Festival. The weekend event will take place at Assiniboine Park from July 17-19, with single day tickets and weekend passes available here.

I scream, you scream 🍦

Adding to our already firmly-held belief that there’s no such thing as too much ice cream, Milksmith now has a third location — this one at The Forks. The pretty pink storefront in the Johnston Terminal joins their other shops at 651 Corydon Ave., and inside McIvor Mall at 1795 Henderson Hwy. (closed for the season).

Get sweaty in St. Vital 💪

Thanks to a tip from one of our readers (hey, Pauline 👋) we have the inside scoop on a new fitness studio opening in St. Vital. The Basement Social Club, located in the lower level units of 166 Meadowood Dr., will offer rhythm cycling (think partying on a bike to the beat of music) and strength training classes. They plan to open in late November.

Stay tuned for details about the Grand Opening, an upcoming pop-up party and more.

Want to see your small business (or your favourite small business) featured here? Reach out to [email protected]

Toews nets first as a Jet 🏒

Last week, we wrote about Jonathan Toews’ triumphant hometown return. This week, we’re stoked to report he scored his first goal as a Jet in Monday’s 2-1 win over the Calgary Flames. Here’s to many more!

Bombers squeak into playoffs 🏈

It wasn’t exactly resounding, but the Winnipeg Blue Bombers’ 17-16 win over the Saskatchewan Roughriders (thanks to a last-second field goal) was enough to earn them a spot in the playoffs. The Bombers finish their regular season against the Montreal Alouettes on Saturday, when they have a chance for 14 consectuve sellouts at Princess Auto Stadium.

Goldeyes drop 2026 schedule ⚾

Circle your calendars for the home opener on Tuesday, May 19 and check out the full schedule here.

Root, root, root for Canada’s Team ⚾

It’s not quite as close to home, but having a Canadian team in the World Series for the first time since 1993 is definitely worth celebrating (don’t let it go to your head, Toronto). Let’s 👏 Go 👏 Blue 👏 Jays 👏

Get your geek on 🦸

Get ready for a weekend of fandom and fun featuring Malcolm McDowell, Ron Perlman, Sean Astin and too many others to name, at Winnipeg ComicCon (Oct. 24-26). Guest panels, photo ops, autographs, cosplay showdowns, gaming zones, hundreds of vendors and more.

Halloween happenings 🎃

If you’re still looking for some ways to celebrate spooky season, some family-friendly options include Witchy Wonderland (Exhibition Park) and Boo at the Zoo (Assiniboine Park Zoo), while some not-so-family-friendly options include Heebie Jeebies, Six Pines and Farmageddon. Check out Tourism Winnipeg’s complete Halloween guide here.

Get lost🌽

For some seasonal outdoor fun, hit up a local corn maze or pumpkin patch. Some popular choices in and around Winnipeg include Schwabe Pumpkins, Deer Meadow Farms, A Maze in Corn, Boonstra Farms and Secord Corn Maze in Dauphin.

Start your holiday shopping at Scattered Seeds 🛍️

Shop small and support local at one of Winnipeg’s biggest craft markets. Scattered Seeds is back at Red River Ex Place for a second straight weekend, with more than 160 vendors selling everything from jewelry and artwork to clothing and candles. More info here.

Support your local theatre company 🐯

Take in Royal MTC’s production of Life of Pi. Based on the best-selling novel by Yann Martel, this epic story of courage, faith and survival roars to life with riveting storytelling and stunning puppetry. Runs until Nov. 8.

Wednesday, Oct. 22

Thursday, Oct. 23

Friday, Oct. 24

Saturday, Oct. 25

Sunday, Oct. 26

Tuesday, Oct. 28

To submit future event listings, shoot us an email at [email protected]

Show me the money 🗺️ An interesting map classifying Winnipeg’s neighbourhoods by social class (based on the 2021 Census) has been getting a lot of traction on Reddit. Check it out here.

Thanks for reading, WPG! Until next time.