Josh Ross « Later Tonight Tour »

Josh Ross brings his Later Tonight Tour to The Colosseum at Caesars Windsor on September 25, 2026. Ontario-born and now based in Nashville, he crafts contemporary country with a pop-rock edge, turning breakups, small-town memories and late-night reflections into melodies that stick. After a pivot from college athletics to music, Ross has shaped a writing style that keeps storytelling at the core while leaning on hooks built for the stage.

Live, he plays with a guitar-forward band that lets the songs breathe and build. The setlist draws on the tracks that first put his name out there — First Taste of Gone, On A Different Night, Trouble, Ain’t Doin’ Jack — alongside newer material shaped on the road. The show moves between slow-burn ballads and up-tempo cuts, with tight grooves, close harmonies and dynamics that carry his choruses. In Windsor, Ross uses Later Tonight to trace the line between modern country and pop without losing the heart of the stories he tells, keeping the focus on the songs and the crowd in front of him.