Toronto’s newest cultural gathering is ready for takeoff. The inaugural Departure Festival + Conference, running May 6–11, features a mix of music, art, comedy, and industry insight with a lineup of performers, celebrity speakers such as Bryan Adams and Matty Matheson, and special events spread across the city. From the ashes of the former Canadian Music Week, the festival still puts music front and centre with a full slate of showcase and premium shows from the next-big-thing to, well, big things. Here are the top 10 shows at this year’s Departure Festival.
Mustafa, May 6, Meridian Hall
Toronto artist Mustafa brings raw emotion and poetic depth to every performance. His relationship with the city is layered — both fraught and fiercely loyal — making any return to the stage here feel especially powerful. Don’t miss this rare opportunity to experience Dunya live, an album that weaves grief, resilience, and community into something profoundly moving.
YHWH Nailgun, May 6, Bovine Sex Club
The Departure Festival has some good showcase shows, like the aforementioned Mustafa concert, but digging deeper could uncover some gems like his band. Known for their explosive blend of punk and avant-garde rock, YHWH Nailgun has earned international buzz, a WME signing, and support from TIDAL’s Rising program thanks to their explosive blend of punk and avant-garde rock. Expect raw noise, sharp edges, and a performance that pushes every boundary. Plus, you get to go to the Bovine Sex Club.
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Dave Chappelle, May 7, Queen Elizabeth Theatre
Comedy icon Dave Chappelle is set to deliver an unforgettable night at Toronto’s Queen Elizabeth Theatre on May 7, headlining one of the most anticipated events of the inaugural Departure Festival. Though the show is officially sold out, a limited number of resale tickets remain available through platforms like StubHub and VividSeats — for those willing to pay a premium. Known for his sharp wit and no-holds-barred presence, Chappelle’s set promises a rare opportunity to witness one of stand-up’s most influential voices in an intimate theatre setting.
Grace VanderWaal, May 7, The Great Hall
After launching her career as a ukulele-toting teen on national television, Grace VanderWaal has undergone a striking transformation. With her new record CHILDSTAR, she emerges as a mature and daring pop songwriter, shedding innocence in favour of edgy, introspective anthems.
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Sister Ray, May 7, Burdock
The SOCAN Songwriters Series sets up shop at The Burdock on May 7 with Mirror Ball, a compelling showcase of introspective lyricism and raw musical storytelling. The evening features Evan Redsky’s vivid narratives rooted in Anishinaabe identity and memory, author-musician Emily Schultz’s literary-infused songwriting, and the haunting, lo-fi confessions of Sister Ray.
Freak Heat Waves, May 7, Dance Cave
For over 15 years, Victoria’s Freak Heat Waves have carved out a unique space in Canadian underground music, blending the jagged intensity of post-punk with hypnotic krautrock rhythms and the glitchy pulse of electronic dance music. Their live sets are a charged swirl of analog grit and digital haze — immersive, relentless, and impossible to pin down.
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SadBoi, May 8, The Drake
The Toronto R&B singer formerly known as Ebhoni is embracing a bold new era as SadBoi. Her breakout verse on Skygirl’s infectious “Wifey Riddim” — alongside Jorja Smith — signaled her evolution into a magnetic, genre-blurring force. She’s carving her own lane with swagger and emotional heft.
Packs, May 9, Dance Cave
Toronto indie rockers PACKS, fronted by Madeline Link, are headlining a solid night of Departure Fest-ing on May 9, at the Dance Cave above Lee’s Palace. The show follows the band’s 2023 album Melt the Honey and recent single “before i was bleeding,” and features support from rising acts Jay Feelbender and Paste.
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Bria Salmena, May 9, The Great Hall
Known for her work fronting the post-punk outfit FRIGS and performing alongside Orville Peck, Bria Salmena now steps fully into her own voice. Her latest release, Big Dog, struts through noir-pop, country noir, and shadowy new wave, all anchored by her singular intensity and lyrical bite.
Pan Arcadia and Cab Ellis, May 11, The Garrison
This powerhouse double bill closes out Departure Festival in style with a blast of raw energy and unapologetic rock ‘n’ roll. Cab Ellis are known for their unhinged live shows and genre-bending chaos, while NYC’s Pan Arcadia, whose dueling guitars, soulful vocals, and anthemic sound have ignited packed rooms from the Bowery Ballroom to festival stages. With both bands on the brink, this show promises unforgettable moments.