Blue Trail of Sorrow

The singer of the lyric remembers being happy walking the streets of his town and now finds sadness everywhere. When he had a dollar, the woman stuck right by him; now he has “nothing but blues for company.” In the chorus he tells her to start walking all over town and keep looking, because he won’t be around. The last verse has him planning to leave the next day, adding that she won’t have any trouble finding him: she only has to look down, where his blue trail of sorrow lies on the ground.

Alison Krauss and Union Station recorded it for So Long So Wrong (Rounder), released in March 1997. It was the band’s first album with Dan Tyminski on guitar, and he sings the lead, with Krauss on tenor and fiddle, Ron Block on banjo, Adam Steffey on mandolin and Barry Bales on bass. The album won the Grammy for Best Bluegrass Album in 1998, and in 2001 Rounder used the song’s title for a various-artists sampler, Blue Trail of Sorrow: 16 Top Bluegrass Gems, which included the Union Station recording.

It had a second recording that same year: Jeanette Williams and Clearwater recorded it at Major Recording Studio in Waynesboro, Virginia, for their 1997 album Blue Ridge Mountain Sun on Mid-Knight. White did not record it himself until 2016, on his album Right Beside You. His version has Vince Gill singing harmony, and Dan Tyminski, Michael Cleveland, Jerry Douglas and Barry Bales among the players.