Caleb Bailey & Paine's Run formed in 2021 due to the success of Bailey's album, Poplar & Pine. Bailey lends lead vocals to the band and is joined by Rob Slusser on banjo, Brandon Kyle on bass, Joe Showalter on fiddle, Chandler Beavers on mandolin, and newest member, Wyatt wood on guitar and vocals. The band is based in the Shenandoah Valley of Virginia and has performed at high-profile fairs, festivals, and concert events this year. Bailey comes from a long line of musical influences in his family. His great grandparents recorded music and were bluegrass promoters, and his great uncle played with Tom T. Hall and Eddie Rabbit as a steel guitar and Dobro player. Bluegrass Unlimited Magazine says Bailey is "an authentic vocalist who gets his important messages across with mature and heartfelt song writing and singing. He's got his own style and messages to share, seemingly beyond his years."