Host, actress, comedian and advocate Lilly Singh will receive this year’s Trailblazer Honours award, recognizing women blazing new trails across radio, television, digital media and music.
Singh joined the Toronto Tempo ownership group last year, in addition to assuming the role of Chief Hype Officer for Canada’s first WNBA team. The Scarborough native rose to fame on YouTube before producing 2016 documentary, A Trip to Unicorn Island, and releasing her New York Times-best seller How to Be a Bawse: A Guide to Conquering Life. She went on to host NBC late-night show, A Little Late with Lilly Singh, becoming the first person of Indian descent to host an American late-night talk show. She’s also a co-owner of National Women’s Soccer League (NWSL) team Angel City FC and president of Unicorn Island, a production company and non-profit fund championing diverse voices through storytelling and advocacy.
The award marks a departure for the Trailblazers organization from the former Rosalie Award, named for legendary CKLW Windsor music director Rosalie Trombley, as Trailblazers expand their borders beyond radio.
This year’s recipient was selected by a newly-established leadership council that included Paul Evanov, CEO of Evanov Communications; Kevin Desjardins, President, Canadian Association of Broadcasters (CAB); Kevin Barton, Co-founder of Departure Festival and Executive Director Pat Murphy; alongside Trailblazers members Hilary Whyte, Director of Sales, English Canada for Bell Media; Sue Mills, former longtime Executive Assistant to the VP of Bell Media Radio; and Chairperson Nancy Brown Dacko, President & CEO of Direct Media Sales.
Singh will be presented with her award during the Departure Honours event on Thursday, May 7, with 2025 Trailblazer Award recipient Sarah Cummings, Director of Radio Content for iHeartRadio & Orbyt Media, to present the award.
Singh will also host a Sports Summit during the Departure Festival + Conference, featuring panels on the Canadian Football League (CFL), the Brodie rec basketball league, and FIFA World Cup.
“We are proud to recognize an international superstar as our 2026 Trailblazer, an exceptional talent whose achievements continue to inspire audiences and industry professionals alike,” said Brown Dacko, in a Departure festival announcement.
Trailblazers has also announced an enhanced prize for its 2026 Next Gen Trailblazer Awards, thanks to the support of The Scotia Women’s Initiative, sponsor of the inaugural Trailblazers Mentorship Program. In a significant boost to the prize package, each of the five winners will now receive a $1,000 cash prize from The Scotia Women’s Initiative, in addition to the existing $1,000 bursary sponsored by Orbyt Media. Winners will also receive the opportunity to attend the Trailblazers panel at Radiodays North America. Nominations close this Friday, April 10.
Departure Festival + Conference has unveiled additional programming and speakers joining the 2026 edition, including the introduction of a new Summit series spotlighting leaders across music, media, sports, and digital culture. The complete schedule is now live at departureto.com.
