Kingston, Ontario, is set for a vibrant late summer as the downtown core unveils a wave of new events, headlined by the first-ever RoadTrip Music Festival and a three-day tribute to The Tragically Hip’s final concert.
The Downtown Kingston BIA is behind the programming, which includes more than 50 free outdoor concerts through its Live 365 series, plus the return of Salsa in the Square and Sydenham Street Commons as a pedestrian gathering space.
RoadTrip Music Festival takes over Princess Street and Springer Market Square on Saturday, September 12, 2026. The one-day event features four stages, with a ticketed mainstage concert at Springer Market Square and a free walkable street festival along Princess Street from 10 a.m. to 5 p.m. The lineup includes headliner Peach Pit, along with Gabriel Jacoby, Kasador, Katie Tupper, Mariel Buckley, Tiny Horse, Absolute Treat, Piner, and O Green. The festival is produced by the Downtown Kingston BIA with consultation from Polaris Music Prize founder Steve Jordan and Wolfe Island Music Festival co-founder Virginia Clark.
Before that, Forever Hip marks the 10th anniversary of The Tragically Hip’s final concert, which took place in Kingston on August 20, 2016. The commemorative series runs August 20 to 22, 2026, and includes a Choir! Choir! Choir! singalong, a screening of the documentary “Long Time Running,” and a CBC rebroadcast viewing party recreating the night 11.7 million Canadians watched the band’s last show. Approximately 25,000 people gathered in Springer Market Square that night in 2016.
Residents can also enjoy free Latin dance lessons at Salsa in the Square every Tuesday through August 25, 2026, with instruction in salsa, bachata, and kizomba. Meanwhile, Play Me Kingston, a public art project featuring 11 custom-designed guitar sculptures, will be on display from mid-August to November 1, 2026, celebrating both the Hip anniversary and the RoadTrip festival.
Full event listings and local business spotlights are available at the Things to Do hub on the Downtown Kingston website.
