By Will McGuirk
Departure Fest 2026 is an unyielding everything everywhere all at once animation of the creative culture community running in Toronto May 4-10 2026. With so much - conferences, awards, performances, presentations, films, talks, podcasts and tributes - one may need some navigation tools and while there are some available on the Departure website we wade in on the Durham Region representation side, and there is a good chunk of us involved from emerging artists to celebs so here’s our plan for the fest:
Before it moved to Oro-Medonte, Boots and Hearts was originally held in Clarington at what was then Mosport, that’s the backyard of Tyler Lorette, a country singer who has been doing the country twang thang since before he could shave and now he’s part of the Departure Fest showcase presented by Boots and Hearts May 7 at the Adelaide Hall. So chuffed for the kat who would have grown up with stories of the fest in the local area and now he gets to be part of it himself.
Another Country artist who is garnering a lot of attention, and one with roots in the Shwarock City, is Sacha. Her song ‘Hey, Mom, I Made It’ and her debut album ‘Woman in the Mirror’ on Sony has been hitting the charts and she is hitting the Departure stage with the SiriusXM Spotlight Series at the Mod Club May 8.
Fab showcase presented by Exclaim and Dine Alone at Lee’s Palace May 9 with our pal, indie emo-rocker Chastity, who wears his heart on his well worn sleeve and always seem to shout out his hometown of Whitby and mos def his second home, the Dungeon, an all ages venue, which gave a lot of Shwarock kids a place to be. Doors open at 7:30 p.m. for this one.
Saturday is a busy night for the Shwarock city rockers as also on the same night is the third annual tribute to Dave Bookman (Bookie) at the Garrison. This year the theme is Big Star songs and stepping up among a pretty rad line-up will be Tauro (Brendan Canning and Cynthia Tauro), and Katie Cruel (Kate Boothman from Kendal). This is a benefit for the Daily Bread Food Bank and admission is with a non-perishable food item donation.
And we wrap up the night with Live at the Bovine, a showcase of acts curated by Cone of Sum 41 (Ajax) and Ian D’Souza of Billy Talent, which features the Almighty Trigger Happy and Iodine, a couple of bands with roots in the D-Rock!
And Cone’s bandmate Deryck Whibley is also involved with Departure as part of an in conversation hosted by music journalist Karen Bliss May 7 at The Bluma Appel Theatre inside the St. Lawrence Centre for the Arts.
Pat Murphy, Executive Director and Head of Programming at Departure Festival + Conference, said in a press release,
“He’s an artist who has helped shape the sound of a generation, and he continues to push forward with the same fearless creativity that defined his career from the start. This will be a compelling conversation about legacy, transformation, and what it means to evolve as both an artist and entrepreneur in today’s music landscape.”
And for us too in Durham Region, Sum 41, is one we look to for inspiration, but we can see Departures is looking at the future, and the acts from Durham Region, highlighted here, represent quite the rosy outlook.
