Virginia’s Caleb Bailey

Hailing from the wellspring of bluegrass and country music, Virginia’s Shenandoah Valley, and living now at the foot of the Blueridge Mountains, Caleb Bailey is carrying on a family tradition rooted in the music of the hills. His great grandparents recorded music and were bluegrass promoters. His great uncle played with Tom T. Hall and Eddie Rabbit as a steel guitar and Dobro player. He previously performed with Allegheny Blue as their lead singer and guitarist and recorded on their albums Greenbrier River and Train Smoke.

He started playing professionally at about age 16 but later put the guitar aside when life outside music got in the way. His break from music came to an end in 2019, after he went through a divorce and weathered the emotional turmoil that goes with it. Subsequently, a songwriter friend encouraged him to record his own songs.

Caleb’s return to full-time music resulted in Poplar and Pine, a ten-track solo debut, which yielded a surprise number one hit, “Grim Reaper.”

His immediate success with original material shouldn’t come as a surprise; he learned early that writing songs was a natural talent (and how to brush off rejection): “I found I could write kind of early on…I understood that when I wrote my first song, but I didn’t put it on paper; I was just singing it to my brother. I told him, ‘We can sing this in church.’ He said, ‘Did Mom teach you that?” and I was like ‘No.’ He was like, ‘Well, how did you find that song?’ and I said, ‘I made it up.’ And he said, ‘That’s stupid, we’re not gonna sing it.’” Despite that minor setback, Caleb’s direction had been set.

Caleb is now in the process of putting the finishing touches on his new band, and lining up performance dates for the summer and fall of 2021so he can get out and share the album and his new music with old and new fans alike.

Visit Caleb’s page here, and listen to the interview here.

By Dan Walsh.