The Winnetka Music Festival takes place June 19-20, 2026 in Winnetka, Illinois, featuring headliners Trombone Shorty & Orleans Avenue, Father John Misty, and Grace Potter alongside 15 other artists. This rock, alternative, indie, pop, and country music festival showcases a diverse lineup including Ben Kweller, Futurebirds, Lucero, and rising acts like Jonah Kagen and Lauren Watkins. The two-day event brings together 18 artists from the United States, United Kingdom, and Australia for a weekend of multi-genre performances. Music fans can expect a blend of established and emerging talent across rock, indie, alternative, pop, and country genres at this Illinois festival.