- Charlie Sizemore — Guitar
- Junior Blankenship — Guitar
- Ralph Stanley — Banjo
- "Curly" Ray Cline — Fiddle
- Jack Cooke — Bass
“Highway of Regret” is credited to Donald “Chubby” Anthony, the fiddler on the Stanley Brothers’ record of it. The composer credit given in the Bluegrass Discography is Ralph Stanley and D. Anthony, published by Starday. The lyric is a man’s lament over a woman who left him for someone else: “Ain’t talkin’, just walkin’ down this highway of regret,” with a heart that is still burning and yearning for the best girl he ever met. He never thought she could be untrue, and wherever he wanders she stays on his mind.
The Stanley Brothers and the Clinch Mountain Boys recorded it in the summer of 1959, at one of the sessions held at radio station WNER in Live Oak, Florida, that produced the LP Mountain Song Favorites. The Bluegrass Discography dates the session 16 July 1959. Carter Stanley sang lead and played guitar. Ralph Stanley sang tenor and played banjo, Chubby Anthony played fiddle, Bill Napier mandolin, and Al Elliot bass and baritone vocal. Starday released it in November 1959 on the single Starday 466, backed with “Another Night,” and on the LP. Billboard reviewed the single on 16 November 1959 and gave both sides three stars; it heard “Highway of Regret” as an upbeat, hoedown-flavoured side.
Ralph Stanley kept the song after Carter’s death in 1966: he recorded it again with the Clinch Mountain Boys for Memory of Your Smile (Rebel, 1982), and Ralph Stanley II included it on Listen to My Hammer Ring (Rebel, 1999). Del & Dawg recorded it on Hardcore Bluegrass in the Dawg House (Acoustic Disc, 2012).
Bob Dylan’s “Ain’t Talkin’,” the closing track of his 2006 album Modern Times, takes part of its chorus from the Stanley Brothers’ song, including the opening line “Ain’t talkin’, just walkin’.” Dylan put the phrase to much darker use.