Three Generations of Leaving also features longtime band members Charlie Rauh on guitar, Oskar Haggdahl on drums, John Gray on upright bass, and Shannon Soderlund on backing vocals, with guests Thad DeBrock on pedal steel and baritone guitar, Mary Lattimore on harp, Philip Kronengold on piano/organ, Burt Levine on banjo, Callie Galvez on cello, and Haruka Horii on violin.