“When You Go Walking,” also known by the line “Wandering in the Darkness,” was written by Roy McMillan, who first recorded it with his band the High Country Boys in the 1970s.
The song is a heartbreak ballad. The singer pictures a former love out walking after midnight, restless and alone, wandering in the darkness much as he does; the night becomes a shared image of loneliness on both sides of a parting.
The Lonesome River Band’s recording brought the song wide notice, and it was nominated for the bluegrass song of the year at the 1996 IBMA awards.