Caleb Bailey & Paine's Run formed in 2021 due to the success of Bailey's album, Poplar & Pine. 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."
Bailey is becoming widely known for his songwriting ability and was chosen as a part of the 2023 IBMA Songwriter Showcase for a co-write with Tim Stafford of Blue Highway, "The Story the Silence Never Told". He also has a co-write with Gaven Largent that was cut by East Nash Grass, "Mountain Bluebird", as well as a #1 song of his own "Grim Reaper", off of his debut album "Poplar & Pine" Bailey has written with the following co-writers: Gaven Largent, Tim Stafford, Chris Burton, Rick Lang, Jack Shannon, Brandon Kyle, and David Morris.