What to see, do, read and hear in Toronto this September

A show that zooms in on iconic pieces of art

As anyone who’s been cut out of a group photo knows, cropping is a powerful tool, and LA-based visual artist Jesse Mockrin uses it to great effect. Her carefully composed oil paintings take famous images and sculptures from the Western canon and zero in on particular aspects, casting the works in a new light. For Echo, Mockrin re-imagines notable pieces from the AGO’s collection in a full-scale exhibition of new works. Her 2024 piece “Fracture” recasts the biblical tale of the judgment of Solomon—and his command that a baby be sliced in two in order to determine its real mother—into a story about maternal love and grief. Opens September 12, AGO Related: Untold stories from the Toronto International Film Festival’s first 50 years

An off-Broadway hit about interracial love

Ever since it debuted in 2018, Jeremy O. Harris’s Slave Play has been provocative and divisive. Take its first act, which opens with a scene of three interracial couples engaging in therapeutic sexual role-play in the antebellum South. One character twerks to Rihanna, another licks his partner’s boots and a third plays Ginuwine’s “Pony” on violin. What follows is hardly subtle, yet the play’s direct and ribald approach has been praised as a surprisingly effective way of exploring the nuances of modern racial politics. September 27 to October 19, Berkeley Street Theatre

A sparkly street fest that brings the community vibes

Summer may be ending, but the city’s block parties are still going strong. It’s Cabbagetown’s turn, and stretches of Parliament and Carlton are closing to cars to make way for blues bands, DJs, Indigenous performers and drag shows. Stilt walkers and acrobats will be dodging streetcar tracks, patios will be serving up craft beer, and food trucks will be dishing out deliciousness. (Last year also featured Oliva Chow chopping cabbages, so there’s that.) The weekend caps off with the annual closing parade, which invites the crowd to follow an Afro-Brazilian drumming band down Parliament to a dance party at Wellesley. September 6, Parliament and Carlton

A comedy show for the sensitive bros

The last time John Mulaney took the stage in Toronto, it was for a show he’d previously cancelled several times, inciting widespread outrage among his Canadian fans. “No one took it as badly as you did,” he joked. Since then, he’s guest-starred on The Bear, started a talk show on Netflix, acted on Broadway and hosted SNL six times. Mulaney is bringing his latest stand-up set to Massey Hall this month, one of several stops on his North American tour, Mister Whatever. Then again, perhaps his return to Canada isn’t entirely by choice: the tour’s promo features the Chicago funnyman blindfolded in the back seat of a car, flanked by faceless goons. September 2 to 5, Massey Hall Related: The biggest celebrities coming to Toronto for TIFF 2025

A play about one woman’s fate in many women’s hands

Twelve people gather in a dusty courtroom to decide the fate of a defendant facing a dubious charge. No, we’re not talking about 12 Angry Men—it’s rural England in 1759, and these jurors are all women. In The Welkin, a woman sentenced to hang tries to escape death by claiming she’s pregnant, and it falls to an all-female jury to decide if she’s a liar. Created by British playwright Lucy Kirkwood, the play is a darkly comic reckoning with law, power and the voices of women. The show’s Canadian premiere is directed by outgoing Soulpepper artistic director Weyni Mengesha. September 4 to October 5, Soulpepper Theatre

A memoir about reporting from the front lines

For decades, CBC foreign correspondent Brian Stewart was Canada’s witness to war, famine and disaster. Now 83, Stewart is taking us behind the camera in On the Ground: My Life as a Foreign Correspondent, a new memoir that’s both a fascinating look at his storied career and a deeply personal meditation on the consequences of observing harrowing history first-hand. Out September 16

A breakup album tour to heal all wounds

The three sisters who make up the rock band Haim may have titled their fourth album I Quit, but that’s clearly not at all the case. After dropping their new record in June, they embarked on a transatlantic tour of the UK and the US, with Toronto as one of only two Canadian stops. Their first album in five years, I Quit takes a more stripped-down, acoustic approach to the band’s usual brand of rock and roll. The refreshed sound may be courtesy of new producer Rostam Batmanglij, who took over after lead singer Danielle Haim split from the band’s long-time collaborator Ariel Rechtshaid. Because who doesn’t love a good breakup record? September 6, Scotiabank Arena

A two-day outdoor art and music party

For two days this month, Trinity Bellwoods Park will transform from the west end’s hottest picnic destination into its largest free open-air gallery for the Queen West Art Crawl. More than 150 local artists are opening up booths around the park’s lower circle while a main stage features live reggae, house, steel band and drag performances, including an appearance by Sanjina of Canada’s Drag Race. The party continues for the littles in a kids’ zone with arts and crafts, family-friendly theatre performances, and storytime with Fay and Fluffy and Betty Baker. September 20, Trinity Bellwoods Park

A “final” show from a legendary band

“The Who announce final tour” has become something of a joke headline in classic-rock circles. The band, now down to half its original lineup, has been playing live since the 1960s, and they say their upcoming tour will be their last. This is, however, a claim they’ve made many, many times before—only to haul the amps back out for yet another stretch on the road. We’ve put together a timeline of all the Who’s not-so-final final tours. September 2 and 4, Budweiser Stage

Tour 1982 In 1978, the band suffered its first tragedy when drummer Keith Moon died of an overdose. Soldiering on, they embarked on a North American tour billed as their last in support of their album It’s Hard. A prophetic title, as lead guitarist Pete Towns­hend clearly wasn’t feeling the magic. At the tour’s final show at our very own Maple Leaf Gardens, he told the crowd, “That’s it. It really has to be.”

Live Aid, 1985 Three years after first swearing off the stage, the band reunited for the now-legendary benefit concert for the Ethiopian famine, joining U2, Queen, David Bowie and others for the blockbuster event. They went on to play the Brit Awards in 1988 and embarked on a reunion tour through North America and England in 1989.

The Who Hits 50!, 2014–2016 Singer Roger Daltrey called this extended jaunt of 70 dates across Asia, Europe and North America the band’s “long goodbye,” hinting that it would be their last. It wound up being longer than expected after Daltrey suffered a bout of viral meningitis that pushed the tour’s planned 2015 finale into 2016.

Tommy and More, 2017 Just a year later, the band did a seven-date twirl through the UK, rocking their greatest hits plus tracks from their 1969 rock opera, Tommy.

The Who Hits Back!, 2022 This post-pandemic tour wasn’t billed as the group’s last, but Townshend was reticent as always, telling an interviewer he was ready to wrap things up for good.

The Song Is Over, 2025 This latest string of shows is being touted as their last one—for real this time, no take-backs, they promise! With Daltrey and Towns­hend now 81 and 80, respectively, they may not be bluffing this time.