Free Winnipeg Jazz Festival Returns

Happy Monday, Winnipeggers!

A huge thank you to everyone who came out to our first-ever Summer of Locals market this weekend. Whether you supported a vendor, grabbed some food, or just showed up to take it all in, we’re so grateful.

Thousands of you showed up, and the energy was everything we hoped for. We’ve got four more markets coming up, with the next one on June 14–15, so if you missed this one, you’ve got more chances to join us.

Thank you again, and if you want to see a recap of the weekend, keep an eye out later in this email for the full experience!

Now, in today’s edition:

  • Manitoba Announces Progress on Ending Homelessness

  • Restaurant of the Week

  • Sea Bears to Retire Chad Posthumus’ Jersey

  • Free Winnipeg Jazz Festival Returns This June

  • Multiple events this week & more

— Jas Singh

News

Manitoba Announces Progress on Ending Homelessness

As many of you know, the Manitoba government has been working to reduce homelessness in Winnipeg for a long time. While recently launching an initiative to help move people from encampments into real housing. And while it’s not an easy fix, this week brought a moment of hope that’s worth sharing.

Through the Your Way Home plan, 67 new supportive housing units are now opening.

Here’s what’s been done so far:

  • It started with a $6.4 million investment, part of a broader $73 million commitment in this year’s provincial budget to tackle chronic homelessness

  • That funding is helping bring 67 new units online, including 26 now occupied and 41 more coming soon

  • 33 people have already moved from encampments into safe, stable housing, and all 33 remain housed with access to mental health, addiction, job, and life skills supports.

  • In the last few months, 17 encampments have been cleared, but new ones continue to appear as more people slip through the cracks.

There’s still a long way to go. But it’s clear that when care and community come together, change is possible.

Let’s hope new housing can be created as fast as the encampments are being cleared, providing real solutions to the problem.

A Message from Paragon Living!

Apartment hunting made easy (and yes, pets are allowed)

If you’ve been apartment hunting in Winnipeg, you probably know how tough it is to find something that’s modern, pet-friendly, and actually feels like home. That’s why these two Paragon Living buildings stood out to us and might be exactly what you’ve been looking for.

Both have bright, 2-bedroom suites with in-suite laundry and free high-speed WiFi. They’re fully pet-friendly, so your dog or cat doesn’t have to miss out. And the best part? You get to choose the lifestyle that fits you best!

Here’s what they offer:

📍 380 Young St
  • Brand-new building just steps away from the U of W

  • Heated indoor parking and 24/7 video surveillance

  • Perfect for students or professionals who want walkability without giving up comfort

📍 333 Wardlaw Ave
  • Right in the heart of Osborne Village

  • Surrounded by cafés, local restaurants, and nightlife

  • A cozy, vibrant neighbourhood that makes it easy to love where you live

So, if you or someone you know is looking for a move-in-ready home, be sure to click below to check out the apartments and view pricing!

P.S. Looking to advertise in the Winnipeg Digest? Reply to this email or reach out at [email protected]!

Restaurant of the Week: Crumb Queen/Andy’s Lunch

Source: Air Canada

Some places just feel like Winnipeg. Crumb Queen/Andy’s Lunch is one of them. It’s small, it’s thoughtful, and every bite feels like it was made with real care.

Tucked into 166 Osborne Street, this cozy little bakery and lunch counter is run by real-life couple Cloe and Andy—two longtime Winnipeg chefs who turned a pandemic pop-up into something special. Think crispy, feather-light crullers, cardamom buns, handmade sourdough, Bianca sandwiches stacked just right, and pasta that makes you pause mid-bite.

They opened their doors in fall 2023, and word spread fast. Not just across Winnipeg, but across the country. And that’s why they were even ranked No. 10 on Air Canada’s Top 10 Best New Restaurants in Canada in 2024.

📍166 Osborne St, Unit 2
🥐 Bakery: Wed–Sat, 10AM–3PM
🥪 Lunch: Wed–Sat, 11AM–3PM

It’s local, it’s heartfelt, and it’s everything we love about this city.

City Sports!

Sea Bears to Retire Chad Posthumus’ Jersey at Home Opener

If you’ve followed the Sea Bears, even just a little, you know the name Chad Posthumus meant more than just basketball. He was the team’s first captain, their first draft pick, and a Winnipegger through and through.

This week on Friday, May 16, at the Sea Bears’ home opener at Canada Life Centre, the team will honour Chad’s legacy in a way that’s deeply fitting: by retiring his jersey number.

Here’s what’s happening:

  • Jersey #33 will be officially retired and raised to the rafters before the game.

  • Players will wear a “33 forever” patch all season long.

  • The city is also naming a stretch of Donald Street “Chad Posthumus Way”.

Chad made a difference on the court, but he made an even bigger one off of it, with local youth, charities, and anyone who needed a boost.

This one’s going to be emotional. But we hope to see you there!

Winnipeg Jets Playoff Update:

Only in Winnipeg could a KFC fully rebrand for a hockey player and somehow, it just makes sense.

The Portage Ave location swapped out Colonel Sanders for cartoon Kyle Connor (aka KFC, if you know the chants). They even flipped the image upside down on the buckets so fans could wear them as hats. And honestly? On Friday night, you couldn’t walk a block without spotting someone rocking one.

And maybe… it brought some magic.

Because the Jets came out flying, shutting out the Stars 4-0 at Canada Life Centre to tie the series. Hellebuyck was dialed in. Ehlers was on fire. The team looked alive again.

Here’s what went down:

  • Jets scored twice in the first 8 minutes

  • Connor Hellebuyck stopped all 21 shots for his first playoff shutout since 2021

  • Ehlers had his first-ever 3-point playoff night

  • The Jets are now 5-1 at home this postseason

And as we’re writing this? Game 3 is underway in Dallas, with the score tied 2-2 at the end of the second.

Let’s hope they can pull it off and take the lead in the series. And hey, keep those KFC buckets handy. They just might be good luck.

The Summer of Locals Market Recap

We still can’t believe what just happened.

This past weekend felt like something out of a dream, and it’s all because of you. Whether you came by for lunch, picked up something handmade, brought the kids to jump around, or simply stopped in to support local, you made it magical.

With over 50 vendors, 10+ food trucks, live music, sunshine, and thousands of Winnipeggers all gathered in one place, it was everything we hoped for and more. The smiles, the kind words, and the pride from small business owners meant the world to us.

Honestly, we’re just feeling so grateful right now.

To keep the good energy going, we pulled together a quick recap video from Day 1 so you can relive some of those moments. And the best part? We’ve got more clips coming your way before the next markets on June 14 and 15, so stay tuned.

Click the button below to watch the full video. And if you were there, hit reply and let us know what you loved most. We’d truly love to hear from you!

Community Digest

Firefighters Save Life in Dramatic Window Rescue

There have been a lot of fires around Winnipeg lately, and while we don’t usually like to focus on negative news, today we just wanted to take a moment to highlight the incredible work of our local heroes.

As reported by CTV News, early Saturday morning, around 1:30 a.m., fire crews were called to an apartment fire on Gaylene Place. Flames were already visible when they arrived, and some people were still trapped inside.

One person had already jumped from a window before firefighters got there. Another was hanging from the window, desperately trying to hold on. Firefighters acted fast and were able to rescue them using a ladder.

Crews launched an interior attack and had the fire under control shortly after 2:10 a.m.

It’s scary to think how much worse it could’ve been. But thanks to the quick work of Winnipeg’s fire crews, lives were saved!

Free Winnipeg Jazz Festival Returns This June

Source: Jazz Winnipeg

There’s something special about summer nights in the Exchange District, especially when Old Market Square is filled with live music, dancing, and a whole lot of Winnipeg spirit.

The Winnipeg International Jazz Festival is back from June 17 to 22, and the best part? Every evening at Old Market Square is completely free. Whether you’re into smooth instrumentals or high-energy funk, there’s a night for you.

Here’s what to expect:

  • Live sets from artists like Apollo Suns, Compost, Brass Queens, Samba Jazz Project, and Flora Luna

  • A return of Latin Night on June 20, celebrating Manitoba’s vibrant Latin music scene

  • Multiple venues across the Exchange District, with Old Market Square hosting all the free shows

Whether you bring a blanket, your dancing shoes, or just your curiosity, the energy downtown is going to be electric.

Manitoba Steps Up to Support Filipino Community After Vancouver Tragedy

What happened at the Lapu-Lapu Festival in Vancouver last month was devastating. Eleven lives were lost, 30 people injured, and the heartbreak has reached far beyond B.C., including here in Winnipeg.

The Manitoba government is stepping up with real support:

  • Matching donations up to $50,000 to the Kapwa Strong Fund

  • To help with trauma care, grief counseling, and emergency support

As Minister Nellie Kennedy said, so many Filipino Manitobans take care of our children, our elders, and our loved ones and now it’s our turn to care for them.

This is about more than just charity. It’s about showing up for each other when it matters most.

Coming up this week:

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

  • Rainbow Kitten Surprise | 8PM, May 14 (Tickets)

    • Location: Burton Cummings Theatre

    • Description: Weaving together lyrical poetry, hummable melodies, and a rush of instrumental eccentricities.

  • The Leaf After Dark: Adults Only Nights | 7-9PM, April 30 (Tickets)

    • Location: The Leaf

    • Description: Enjoy an adults-only atmosphere with live musical entertainment, plus wine and beer.

  • Chris D’Elia Comedy | 8PM, May 15 (Tickets)

    • Location: Burton Cummings Theatre

    • Description: An American stand-up comedian, actor, writer, and podcast host. He is known for playing Alex Miller on the NBC sitcom Whitney, Danny Burton on the NBC sitcom Undateable, Kenny on the ABC television series and more!

  • Winnipeg Sea Bears vs Edmonton Stingers | 7:30PM, May 16 (Tickets)

    • Location: Canada Life Centre

    • Description: Home opener and Chad Posthumus’ jersey retirement.

  • Manito Ahbee Festival | May 16-18 (Tickets)

    • Location: Red River Exhibition Park

    • Performers: A celebration of Indigenous arts, culture and music. Includes the signature Powwow, Ball Hockey Tournament, Ignite Our Spirit Performance Stage and Indigenous Marketplace.

  • Foodtrip Market SpringFest | 12-9PM, May 17 (More Info)

    • Location: IKEA, 500 Sterling Lyon Parkway

    • Description: Join us for Foodtrip Market SpringFest, a day full of blooming joy, delicious food, and local treasures. Pet fashion show, local vendors, handmade crafts, food stalls, live music and more!

  • Tyndall Community Market Kick Off | May 17-18 (Free/Learn More)

    • Location: Tyndall Park Community Centre

    • Description: Enjoy food trucks, local vendors, free Zumba, games, music, and more—featuring The Food Park. Free admission and great vibes, so be sure to come!

  • Andres Cepeda Concert | 8PM, May 18 ($)

    • Location: Burton Cummings Theatre

    • Description: Born in Bogotá, Colombia, Andrés Cepeda is one of the most renowned singers and songwriters in the Latin American music scene.

Exciting Events: May 12th & 13th

Sports🏀

  • Live Horse Racing | 7:30PM, May 13-14 (free/learn more)

    • Location: Assiniboia Downs

Music 🎵

  • Sean Taylor | 12PM, May 12

    • Location: Belle's Kitchen + Music Hall

  • Courriers | 7PM, May 13 ($)

    • Location: Sidestage Winnipeg

  • David Alpert (A Summer Camp Massacre) | 7:30PM, May 13 ($)

    • Location: Park Theatre

    • Note: PG 13

Family Fun🎆

  • The Forks Workshop Series | 6PM, May 12

    • Print With Jer | The Forks (free/learn more)

      • Description: Block printing workshop at the Pop-Up Kiosk in The Forks Market! Get hands-on as you carve and ink a rubber block to create a custom print featuring your birth flower.

    • Cookie Decorating Workshop | The Forks (Tickets)

      • Description: Get six cookies (three of each shape) and four colours of icing. Live instructions will be given step by step to complete your cookies within the two-hour class time

  • Manitoba Day | 11AM - 3PM, May 12

    • Location: Manitoba Children's Museum

    • Description: Manitoba Day is the perfect day to learn more about this province we call home

  • Dragons and Mythical Beasts | 9:30-10AM, May 13 (Tickets)

    • Location: Burton Cummings Theatre

    • Description: From the creators of the international smash hit Dinosaur World Live who bring spectacular puppets to life, Dragons and Mythical Beasts is coming to Canada for the first time.

  • Toddler Tuesdays at The Leaf | 9:30-10AM, May 13 ($)

    • Location: Mediterranean Biome at The Leaf

    • Description: Your little one will enjoy music and games while discovering the joy of movement!

  • ELEVATE: Manaaji'idiwin Play | May 13-17 (Tickets)

    • Location: John Hirsch Mainstage

    • Description: What happens when the elevator gets stuck on your way to an important meeting?

Special Events 🎨

  • Brian Kiley Comedy | May 13-17 ($)

    • Location: Rumor's Restaurant and Comedy Club

    • Description: Brian Kiley was a staff writer for Conan O’Brien for 27 years and wrote on the final season of “Ellen.” He has been nominated for 16 Primetime Emmy Awards and 2 Daytime Emmy Awards!

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