[citation needed] His parents had migrated to Ohio from eastern Kentucky in the late sixties, and Castle was exposed to Appalachian Music from a very early age.

[citation needed] Castle spent his teen years as a staff-writer in Nashville, Tennessee, working under such notable writers as Casey Kelly, Wood Newton, and Earl Bud Lee.

[1][better source needed] Castle enrolled in Bowling Green State University as a political science major, where he met Pulitzer Prize winner Edward Albee in 2006.

That same year, Castle was named featured artist at Folk Alley,[4][better source needed] in addition to being a finalist in the Granite State Songwriting Contest, in Newmarket, New Hampshire.

[citation needed] In June of 2023, he returned to Woodstock to join producer Larry Campbell, engineer Justin Guip, and bassist Brandon Morrison at Milan Hill Studios to record Long Way to the Bottom, his first full-length album in more than ten years.

The ten song LP includes material written between 2006 and 2023, and prominently features Campbell's string work on guitars, mandolin, fiddle, and pedal steel.

[8][better source needed] Imagine Norwalk hosted several community-wide events throughout the summer of 2014 and 2015, which bolstered the local economy and garnered an exciting degree of citizen participation.