“Cold Virginia Night” was written by Tim Massey and first recorded by Ronnie Bowman as the title track of his 1994 album on Rebel (REB-CD 1704). The session was held at Doobie Shea Studios in Ferrum, Virginia. On the song Bowman sings lead with Dan Tyminski on harmony and plays bass, with Tony Rice on rhythm guitar, Craig Smith on banjo, Tyminski on mandolin, Alison Krauss on fiddle and Kim Gardner on dobro.
The lyric is told by a man looking back on a love that ran through the seasons: it began on a sunny spring morning, grew like flowers on the mountain, turned hot as a summer wind and then fell with the autumn leaves. It ended on a full-moon night in Virginia when Jenny left him, and the refrain returns to her “frostbitten heart.”
At the 1995 International Bluegrass Music Association awards, Bowman’s recording won Song of the Year, with Massey credited as writer, and the album won Album of the Year. Rebel put the track on its 1996 compilation 35 Years of the Best in Bluegrass, 1960–1995, and Sugar Hill included it on Choice Picks in 2000. Other groups have recorded it since, among them the Buckeye Bluegrass Band on Just for the Fun of It (Starr, 1996), BorderLine, from Pennsylvania, on Unleashed (2015) and Blueland on More Than Enough (2018).