His chapbook of poetry, Sabbatical on Winifrede Hollow was published in 1993 by Trillium Press (St. Albans, West Virginia)(with a second edition appearing in 1998). In 1992 he won a writer's fellowship from the West Virginia Commission on the Arts. Caldwell's poems also appear in Barbara Smith & Kirk Judd (eds.), Wild Sweet Notes: Fifty Years of West Virginia Poetry 1950-1999 (Publishers Place, 2000).