Jazz, and all that Downtown’s summer festival season about to get into the swing of things By: Conrad Sweatman Posted: 2:00 AM CDT Tuesday, Jun. 17, 2025 Last Modified: 1:54 PM CDT Tuesday, Jun. 17, 2025 Updates

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‘We’re a city of spectacle,” University of Winnipeg professor of geography Jino Distasio told the Free Press last month. “We like a party, and also we find ourselves using the downtown as the stage for those parties.”

Of course, outside the Winnipeg Whiteout Street Parties during hockey playoffs, summer and early fall are the city’s spectacle seasons — starting in full swing with the annual Winnipeg International Jazz Festival.

For a week in June, seemingly every downtown venue and back alley, real stage or makeshift one, courses with music and people, with Old Market Square as the party’s centre of gravity.

“Jazz fest is synonymous with Old Market Square,” says Jazz Winnipeg’s artistic director Zachary Rushing. “For most people, when you say ‘jazz fest’ here in Winnipeg, that’s (what) they think of.”

From tonight to Saturday, free concerts at Old Market Square happen every night, and some afternoons, boasting such out-of-town acts as the Free Label, Kimmortal, Brass Queens and New Jazz Underground, and locals including Jana Jacobs, Compost, CEC x No Fuss, Mari Padeanu, Vox Populi and Apollo Suns.

Crowds can wander between these groove-heavy sets, staying hydrated at the beer gardens, and nearby indoor venues such as Little Brown Jug and the Fort Garry Hotel Club Room. There they’ll find jazz club vibes, with ticketed concerts by such local jazz leaders as Will Bonness, Marco Castillo, Amber Epp and Larry Roy, among others and a few more out-of-towners.

The contrast between the two types of concerts — free outdoor and ticketed indoor shows — can feel emblematic of a growing split within international jazz festivals between pop and traditional jazz programming that sometimes irks jazz purists.

While Josh Daniel — lead singer of six-piece Toronto act the Free Label, which plays 11 p.m. at Old Market Square — strikes the stance of budding pop star, it’s hard to miss the jazz accents that colour his band’s disco and R&B sound. He feels the jazz-pop schism is a little overblown.

“Well, everything always goes back to the roots, right? Blues and jazz are huge influence for us, and we all studied it.”

After a big year, which saw the band’s online fanbase skyrocket, the Free Label played Winnipeg Jazz Fest for the first time last summer, closing out the Old Market Square series.

The band strutted in co-ordinated steps and outfits, like an old-school Motown or soul band — even holding the band’s keytar player Jacob Thompson on his head while he improvised over chord changes that showed off the players’ jazz-school chops.

Daniel says the concert, which packed the space between Bannatyne, King and William with raucous Winnipeggers, was one of the band’s favourites of that tour.

“When we pulled in, there were some amazing jazz musicians playing, and they were ripping. They were unreal and it was awesome to see,” he adds.

Festival headliners this year include a number of heavy hitters who also blur genres.

There’s Bela Fleck, joined by notables Edmar Castañeda and Antonio Sanchez, whose cosmic bluegrass jazz fills the Burton Cummings Theatre tonight with openers the Diogo Peixoto Trio.

The 16-time Grammy-winning Fleck is certainly the world’s most famous living banjoist, an unusual distinction for a jazzer.

Headliner Madeleine Peyroux, who made her name 20 years ago singing retro jazz in the vein of Billie Holiday and Edith Piaf, performs tomorrow night, with velvet-voiced local singer Erin Propp opening.

Peyroux’s touring a new album, Let’s Walk.

“It’s really the best of her work that’s happened in a long time. It’s a true return to form in terms of her folk, jazz songwriting roots,” Rushing says of the American singer-songwriter.

With more than 50 concerts at this year’s festival, there’s no shortage of things to see during the week. But Winnipeggers will have to wait until Saturday for the next headlining act, when vocalist Jimmie Herrod and American pianist George Colligan take the stage after precocious local opener Jovelle Balani.

“So many in Winnipeg will be familiar with George Colligan, because he used to be the professor of jazz piano at the University of Manitoba, while Jimmie might be a newer discovery,” says Rushing.

While Herrod plays with Pink Martini, one of the world’s best-known pop-jazz acts, he’s become a rising star in his own right — earning Sofia Vergara’s Golden Buzzer on America’s Got Talent in 2022, with his performance racking up more than 17 million views on YouTube.

Cameroon-born multi-instrumentalist Richard Bona — who also offers a free jazz clinic the same afternoon — closes out the festival on Sunday, with magnetic Afro-fusion local opener Dr Henry. A self-taught prodigy, Bona built his own instruments as a child and was later inspired by Weather Report bassist Jaco Pastorius. Now a jazz professor at NYU, Bona has toured with legends including Quincy Jones, Sting, Pat Metheny and Harry Belafonte.

All the headlining acts, except Bela Fleck, perform at the state-of-the-art Desautels Concert Hall at the University of Manitoba.

conrad.sweatman@freepress.mb.ca