Josh Ross « Later Tonight Tour »

Josh Ross brings his Later Tonight Tour to Casino Rama in Orillia on September 26, 2026. The Ontario-born, Nashville-based singer-songwriter threads modern country rock with a dusky edge, a warm vocal rasp and plainspoken, heart-first writing. On stage, he leads a tight, guitar-forward band through power ballads and barroom anthems built for a chorus, mixing confessional detail with hooks that stick.

The set leans on songs that have mapped his rise: Trouble, the dusky ballad that hit #1 in Canada and went RIAA Gold in the U.S.; the swaggering Single Again, a radio favorite on both sides of the border; and early standouts like First Taste of Gone, On A Different Night and Ain’t Doin’ Jack. Between the singalongs, Ross keeps the storytelling close to the bone—breakups, small-town memories, late-night reckoning—while letting the dynamics breathe live.

Named CCMA Entertainer of the Year and honored with the CMA’s Jeff Walker Global Country Artist Award, Ross carries real momentum into this tour. At Casino Rama, he lines up a set that balances new material with fan staples, aiming squarely at that space where country, pop and rock meet.