Midweek check-in, Winnipeg 💙

First off, thank you for the incredible response to the Winnipeg Dinner Club we shared on Monday. The messages, sign-ups, and excitement have been so fun to see. It really means a lot, and we can’t wait to share more soon.

Today’s edition is packed with a few things worth knowing and looking forward to. We’ve got new shows coming to the city, details on the Jets alumni game, and a couple of other updates that have been buzzing around Winnipeg this week.

So stay warm, grab a coffee or something cozy to sip on, and let’s jump into it.

Now, in today’s edition:

— Jas Singh

If winter’s been feeling a bit long lately with the cold weather and snowstorms, here’s something genuinely nice to look forward to.

Two major tours just added Winnipeg stops for 2026, both landing at Canada Life Centre, and they bring very different kinds of excitement.

First up, a night that’s all about laughs.

Gabriel Iglesias is bringing his brand new tour to Winnipeg this spring, fresh off the success of his latest Netflix special and packed with all-new material.

Comedy shows like this tend to sell out quickly, so this one’s worth planning ahead.

Click Here: To get details and ticket info for Gabriel Iglesias.

And if comedy isn’t your thing, there’s a big summer concert on the way too.

Creed is bringing its Summer of ’99 Tour to Winnipeg after huge demand across North America, with special guests Mammoth.

If you’re hoping to go, presale is your best bet.

Click Here: To sign up for presale access and see full tour details!

Two very different shows, two very different crowds, and a good reminder that even in the middle of winter, there’s always something to look forward to in Winnipeg.

Making new friends isn’t always easy. Life gets busy, routines settle in, and meeting new people can start to feel harder than it should.

That’s exactly why we created the Winnipeg Digest Dinner Club.

Nearly 100 of you are already booked for upcoming dinners, and it’s been genuinely exciting to watch this little idea turn into something real. Small tables. Thoughtful matching. Local restaurants. And conversations that don’t feel forced.

Each dinner brings together six people at one table, matched through a short quiz so you’re not walking in blind. And because we host these on Wednesday nights, it also helps support local restaurants on a quieter evening.

If you’re thinking about joining, don’t wait too long. As we need time to book reservations and make it easy for the restaurants hosting us.

This weekend is shaping up to be a fun one, especially if you’re looking for something lively that also gives back.

Wrestling For A Cause is back with its annual live pro wrestling fundraiser, bringing together local talent, big personalities, and a crowd that’s there for a good reason.

For the fourth year in a row, Manitoba wrestlers will step into the ring to put on a memorable show while raising money for The Dream Factory.

A local organization that helps families across Manitoba create meaningful experiences for kids facing serious illnesses, and this event helps make those moments possible.

It’s shaping up to be a fun night out that combines live entertainment with a chance to support kids and families in our community.

Click Here: To get tickets or donate in support of The Dream Factory!

The Heritage Classic weekend is already shaping up to be a special one for Winnipeg hockey fans, and the Jets are adding an extra moment of nostalgia before the main event.

Ahead of the Heritage Classic at Princess Auto Stadium on Oct 25, the Jets will host an alumni game on Oct 24, bringing some very familiar names back together for one night.

The alumni game will feature former players from Winnipeg and Montreal, giving fans a chance to see past favourites share the ice again before the rivalry resumes the next day.

For longtime fans, this feels like a full-circle moment. It’s a chance to celebrate the players who helped shape modern Jets history, reconnect with those memories, and kick off a big weekend at Princess Auto Stadium in the best way possible.

Click Here: To see all the details and share which Jets players you’d love to see added next.

For many communities, places of worship are more than just buildings. They’re spaces where people come together, support one another, and feel grounded.

With hate-motivated incidents becoming more common, the province says it wants to help protect those spaces.

Manitoba has announced a $1 million Security Enhancement Fund aimed at helping places of worship and cultural organizations improve safety and recover after hate-related incidents.

The province says application details and timelines will be shared in the coming weeks. In the meantime, organizations can already reach out by email to get more information.

Click Here: To learn more about the Security Enhancement Fund and how to apply.

Winnipeg just hit a milestone that feels worth pausing on.

New data from Statistics Canada shows our city’s population has officially passed 850,000 people, a sign of how much momentum Winnipeg has right now.

Scott Gillingham says this kind of growth reflects growing confidence in Winnipeg as a place to put down roots, build careers, and raise families. He also pointed out that growth brings responsibility.

As more people call Winnipeg home, the focus stays on getting the basics right. Things like housing, transit, and long-term infrastructure that support everyday life and help the city grow in a way that feels sustainable and fair.

Click Here: To read the City of Winnipeg’s full update on the population milestone.

This section includes only the major events happening soon. For a complete list of all events, you'll have to wait for future editions!

Events marked with (Tickets / $) require advance purchase. Double-check dates before heading out!

Thanks for reading The Winnipeg Digest! Let’s chat again on Friday!

P.S. Want to get your business in front of thousands of local Winnipeggers? Email us at [email protected].