Songfacts®:

• Red Wing was a famous boys' reformatory in Red Wing, Minnesota. Many of Dylan's early fans believed that Dylan himself had been incarcerated in Red Wing, but he never was. Further, there are many Minnesotans familiar with the place that doubt that Dylan ever laid eyes on it at all, as the school resembles a college much more than a prison, as he depicts it in the song.
• Dylan performed this song live on occasion from 1963-1964, but it wasn't released until it appeared on the 1991 collection The Bootleg Series Volumes 1-3 (Rare & Unreleased) 1961-1991.
• In March 2021, the earliest known recording of this song emerged. The recording quality is poor, with the cacophony of patrons' voices overwhelming Dylan's music, but it's still unmistakably him in the background. We don't know who recorded it, but we do know that it was captured sometime in December 1962. Previously, it had been thought that the first recording of the song was April 12, 1963, at Town Hall in New York City.
• Dylan recorded this song on April 24, 1963, during the final sessions for The Freewheelin' Bob Dylan, his second album. The song didn't make the final cut.
• One-time Dylan lover, friend, and collaborator, Joan Baez recorded this song in 1968 on her album Any Day Now. In 1998, Ramblin' Jack Elliot recorded a version on his album Friends Of Mine.
• Dylan borrowed the song's melody from a Scottish ballad titled "The Road And The Miles To Dundee," which can be traced back as far as 1908. Dylan likely found it while traveling through England three months prior to starting work on The Freewheelin' Bob Dylan.