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Departure Festival Takes Over Toronto: A Live Reimagining of Canadian Music Week
By: Cynthia Florek
Toronto is alive this week with the pulse of innovation, creativity, and cultural exchange as Departure Festival + Conference transforms the city into a multidimensional hub of music, comedy, visual arts, and thought leadership. Running from May 6–11, Departure reimagines the spirit of Canadian Music Week, blending the legacy of the past with the energy of the now.
A Living, Breathing Citywide Festival
As the festival unfolds across 40+ venues, over 3,000 delegates and thousands more fans flood Toronto’s streets—from Queen West’s indie hideouts to the historic halls of Massey Hall and Meridian Hall. The lineup showcases not just musical talent, but a broader cultural movement that includes live comedy, culinary arts, visual exhibitions, and forward-thinking panels.
“We’re not just celebrating music,” says Liam Osei, Festival Director. “We’re celebrating departure—as in innovation, risk, transformation. That’s what makes Toronto the perfect host.”
Headliners Creating Cultural Moments
From the moment Mustafa steps onto the Meridian Hall stage with his haunting poetry-pop fusion, the tone is clear: Departure is emotional, bold, and deeply rooted in identity.
On May 7, comedy icon Dave Chappelle electrifies the Queen Elizabeth Theatre with his sharp, unsparing stand-up, leaving no topic untouched and no audience member unmoved.
Later in the week, Bryan Adams reminds the city why he’s a national treasure, delivering anthemic classics to packed crowds. Also commanding attention: Tia Wood, the Indigenous star whose performance at The Drake Hotel on May 9 is equal parts ceremony and celebration.
The Conference at Hotel X: Innovation in Real Time
At Hotel X Toronto, creatives and executives converge for Departure’s conference, where over 100 speakers discuss everything from the future of AI in music to the evolution of Black Canadian artistry. Culinary icon and TV personality Matty Matheson leads a fiery talk about cultural storytelling through food and fame. Meanwhile, digital disruptors and label veterans debate the fate of the album format and artist autonomy in an era of algorithmic taste.
More Than Music: Art, Podcasts, and Culture Collide
The visual arts component comes alive at Taglialatella Galleries, where artists Danny Hastings and Justin Bua exhibit powerful works reflecting hip-hop and diaspora narratives. And at Massey Hall, the cult-favorite podcast “How Did This Get Made?” records a live episode on May 9, blending film geekery with Departure’s signature energy.
Toronto as the Perfect Host
Toronto doesn’t just host Departure, it embodies it. The city thrives on movement, on flux, on stories being written and rewritten. Departure Festival amplifies that ethos, inviting residents and visitors alike to experience creativity in its rawest form.
“Toronto is a city of departures,” says Osei. “Immigration, reinvention, constant change, it’s all here. This festival is just an echo of what already makes this city great.”
How to Join the Experience
Whether you’re attending as a music lover, creative entrepreneur, or curious observer, Departure offers tiered passes (Priority, Conference, Comedy & Culture) available through departureto.com. With major events still ahead, now is the time to plug in and experience what it means to leave the old behind and discover what’s next.
