Toronto’s biggest jazz festival kicks off this Friday, and there’s a lot going on that fans will surely want to catch. Between the headlining concerts, the free shows along Bloor Street and the many other gigs and festivities around the city, there’s plenty to do and tons of choices.

Here’s a day-by-day guide to some of the highlights as we help you prepare for the TD Toronto Jazz Festival.

Make sure to drop by the JAZZ.FM91 tent during the festival! We’ll be at the corner of Bloor Street West and St. Thomas Street on June 22, and the corner of Cumberland Street and Bellair Street from June 2830. You can enter to win one of our amazing daily prizes and have a chance to win our grand prize of a trip for two to the Barbados Jazz Excursion.

Friday, June 21

Hot 8 Brass Band
TD Mainstage on Cumberland Street • 8:30 pm

Helping to kick off the festival’s opening weekend is the Grammy-nominated Hot 8 Brass Band, one of the most ubiquitous funk-style brass bands of the last 20 years. The New Orleans group has toured with popular R&B singer Lauren Hill and has been featured in two Spike Lee documentaries and the HBO series Treme. The band’s story is “one of tragedy and triumph,” having suffered through the deaths of four original members due to illness and street violence and lived through their city’s devastation by Hurricane Katrina. But time and time again they have rallied around their community and brought their hot, fun and funky shows to audiences around the world. On this occasion, JAZZ.FM91’s Gumbo Kitchen host and resident NOLA expert Ronnie Littlejohn is emceeing this show.

Here’s what else is happening that day

Saturday, June 22

Downchild Blues Band with Dan Aykroyd and more
TD Mainstage on Bloor Street West • 8:30 pm

This year marks the 50th anniversary of the Downchild Blues Band, which inspired the famed SNL skit and feature film The Blues Brothers with Dan Aykroyd and John Belushi. The legendary group will be playing a free concert with Aykroyd along with Paul Shaffer, David Wilcox, Gene Taylor, Kenny Neal and Erja Lyytinen. With a lineup and occasion like this, you know it’s going to be an incredible party.

Amanda Martinez with Kellylee Evans and more
Isabel Bader Theatre • 8 pm

After a great Live to Air concert here at JAZZ.FM91, Amanda Martinez is kicking off her new album Libre at the Isabel Bader Theatre. With Libre, Martinez takes stock of her place as an artist, friend, daughter and mom with a rich, lived-in mix of African and Latin-American styles. Produced by Juno Award-nominated Kevin Laliberte, it’s her most musically eclectic recording yet. Saturday night’s show will be emceed by JAZZ.FM91’s Café Latino host Laura Fenandez, and Martinez will be joined by special guests Kellylee Evans and Donne Roberts for what will be a great time with lots of love to go around.

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Sunday, June 23

TD Mainstage on Bloor Street West • 7:30 pm

Widely admired Canadian recording artist and broadcaster Shad has specially curated a show featuring unique acts Oddisee & Good Compny and Elaquent. He’ll then close out the evening with a headlining performance of his own. For those looking to mix their jazz with a hip-hop flavour and experience a show like no other, look no further than this pulse-raising, boundary-pushing lineup of artists assembled by one of Canada’s best.

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Monday, June 24

Diana Ross
Sony Centre • 8 pm

The biggest name in this year’s lineup takes the stage on Monday night. Having just celebrated her 75th birthday this year, Ross will bring her legendary voice to the Sony Centre for a showcase of songs from a career spanning more than five decades. With numerous smash-hit albums and singles, Diana Ross is in the upper echelon of Motown-era stars. And this is your chance to see an icon right here in Toronto.

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Tuesday, June 25

Tower of Power
Danforth Music Hall • 8 pm

It’s the 50th anniversary of this legendary Oakland band, and they’re ready to celebrate it in style. Since 1968, Tower of Power has held a high reputation in soul, rock and pop music thanks largely to the sophistication and punch of their jazz spirit. And while R&B groups of their time morphed into the synth sounds of the ’80s, Tower of Power stayed the course and almost single-handedly kept the sound of the full 10-piece band alive. With JAZZ.FM91’s music director and Afternoon Drive host Brad Barker set to emcee the show, prepare to be funkified and energized by what has to be the one of the best opportunities to see this iconic group — a huge party.

Emilie-Claire Barlow
Koerner Hall • 8 pm

For those looking for a different vibe that night, Emilie-Claire Barlow has you covered. A favourite in Canadian vocal jazz, this singer will being a  warmhearted mix of classic pop and jazz tunes to beautiful Koerner Hall. On her current tour looking back at her career so far, Barlow has put together a tour-de-force performance of songs from her 12 albums — a retrospective on the first 20 years of her life as a musician and, surely, an affirmation of all that’s still yet to come.

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Wednesday, June 26

Norah Jones
Sony Centre • 8 pm

We probably don’t need to tell you about Norah Jones. But just in case: She’s won nine Grammy Awards, sold more than 43 million albums, and has established herself as one of the most popular cross-genre artists in modern music, with a sound that melds jazz, folk, country, rock and soul. She’s currently touring in support of her seventh studio album Begin Again, released this year. Expect to hear some of those new tunes along with huge hits like Don’t Know Why and Come Away with Me.

Omara Portuondo
Koerner Hall • 8 pm

After an incredible 70-year career — 70 years! Seventy! — this Buena Vista Social Club diva has finally decided to say farewell. And at 88 years old, she’s doing so with a worldwide tour. The great Cuban diva is celebrating with a grand fiesta highlighting the impressive span of her career, and you’re invited. Get a taste of Cuban classics like Besame Mucho and Veinte Años, and be there with emcee Laura Fernandez as a nearly unstoppable force of music says goodbye. At the end of it all, Portuondo promises to “always leave them wanting more.”

Ghost-Note and Rinsethealgorithm
Horseshoe Tavern • 9 pm

Wednesday night is pretty stacked. Over at the Horseshoe, local bassist Rich Brown’s rinsethealgorithm is joining forces with Ghost-Note — a new project from Snarky Puppy’s percussion duo Robert “Sput” Searight and Nate Werth — for an exciting double bill. Get ready for a hotly anticipated live show with explosive rhythms and breakneck funk, brought to you by a superpowered bill of modern jazz trailblazers.

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Thursday, June 27

Cécile McLorin Salvant and Sullivan Fortner
Koerner Hall • 8 pm

Just about every time this young jazz star releases an album, she wins a Grammy Award for it. Cécile McLorin Salvant has won four Grammys for the four records she’s made in the last six years — including this year for her 2018 album The Window — and she’s won praise from critics and jazz icons alike. All that and she’s only 29. She’ll bring her impeccable, pitch-perfect voice to Koerner Hall, accompanied by virtuosic pianist Sullivan Fortner and emceed by our Dinner Jazz host John Devenish. Toronto-based Juno-winning drummer Ethan Ardelli, a regular at JAZZ.FM91’s concerts, will open the show with his quartet.

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Friday, June 28

Laila Biali with William Sperandei
TD Mainstage on Cumberland Street • 8:15 pm

Fresh from her accomplishment at this year’s Juno Awards, Canadian jazz-pop star Laila Biali is playing a free outdoor show on the second Friday night of the festival. With all the accolades and excitement over her Juno-winning album and with the backing of the renowned William Sperandei, this is a must-see.

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Saturday, June 29

Shuffle Demons
TD Mainstage on Cumberland Street • 8:15 pm

They’ve got style, they’ve got flare, and they’ve got talent. The Shuffle Demons broke onto the Canadian music scene in the ’80s with their TTC-themed classic Spadina Bus, and since then they’ve brought their crowd-pleasing ways to audiences both in Canada and around the world. Expect an exciting, no-holds-barred performance that’s likely to include wild romps through the crowd, free-jazz moments, danceable funk, poetry, killer solos and probably a whole lot more. Depending on where you’re coming from, you might even hop on the 510 to get there.

Chris Potter Quartet
The Rex • 10 pm

Downbeat Magazine called him “one of the most studied (and copied) saxophonists on the planet.” JazzTimes labelled him “a figure of international renown.” In short, Chris Potter is one of the leading composers, bandleaders and soloists of his generation. Catch him and his quartet in the storied setting of The Rex to keep your Saturday night rolling with world-class jazz.

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Sunday, June 30

Larnell Lewis Band
TD Mainstage on Cumberland Street • 8:15 pm

There’s plenty happening on the final day of the festival, and Toronto sensation Larnell Lewis is the one who will be closing out the TD Mainstage. One of Canada’s most promising drummers, Lewis has gained international status for his work with three-time Grammy winners Snarky Puppy, and his own debut album In the Moment was nominated for a Juno this year. Come experience his personal blend of jazz, fusion and Afro-Caribbean roots as this year’s edition of the TD Toronto Jazz Festival comes to an end.

Here’s what else is happening that day

Of course, there are hundreds of other shows over the 10 days of the festival, with something for just about everyone. You can check out the full lineup here. We’ll see you out there!