Songfacts®:

• Dylan wrote this song about his girlfriend Suze Rotolo, who is the woman holding his arm on the cover of The Freewheelin' Bob Dylan. Specifically, he wrote it to exorcise the heartache he felt when she left New York to study for eight months in Perugia, capital city of the region of Umbria, Italy.
  
  My baby took my heart from me
  She packed it all up in a suitcase
  Lord, she took it away to Italy, Italy
  
  Sometimes Dylan's songs require teams of psychoanalysts and cryptographers to break, but in this case we know what it's about because Dylan explicitly stated it in a letter to Rotolo. He told her he'd just recorded some new songs, two of which were about her: "Down The Highway" and "Bob Dylan's Dream," which is also on The Freewheelin' Bob Dylan.
  
  It's interesting to look at this song and this letter in that very human context because it all happened shortly before Dylan blew up as a star. He had already released his first album, Bob Dylan, but that one hadn't made many waves outside the relatively small folk music community. It was with Freewheelin' that Dylan would start breaking out as a genius of his generation. So, there he was, a young man unknowingly on the cusp of immortality, pining away in heartbreak like any 22-year-old.
• Part of Dylan's power as a musician is his ability to channel depths of emotion on command, but the anguish heard in "Down The Highway" was sincere. He was so broken up by Rotolo's absence that their mutual friends expressed anger with her upon her return for the pain she caused.
  
  Rotolo, a committed communist who heavily influenced Dylan's early political songs, had gone to Italy to study, but their relationship was also strained by many factors, from Rotolo disliking the pressure of being with a growing star, to Dylan's need for a protector, to her parents strongly disapproving of them living together. Later, Dylan's intensified fame, his affair with folk-queen Joan Baez, and an abortion proved too much, and their relationship ended.
  
  Rotolo spent the remainder of her life as an artist and a political activist. She published a book in 2008 titled A Freewheelin' Time: A Memoir of Greenwich Village in the Sixties.
• Yes, I'm a-walkin' down your highway
  Just as far as my eyes can see
  From the Golden Gate Bridge
  All the way to the Statue of Liberty
  
  The Golden Gate Bridge is in San Francisco and the Statue of Liberty is in New York, so the two together act as bookends of America. Going from one to the other means crossing the country.
• Dylan recorded "Down The Highway" in Studio A of Columbia Recording Studios on July 9, 1962. It was the third recording session for Freewheelin'. He got this one and six others down in a single take, which is remarkably considering the impact that this album had on music and culture as a whole. Freewheelin' not only acted as a rallying cry for progressive political activists, it also elevated the expectations of lyrical poetry and depth.
  
  The other six songs recorded in one take that day were "Baby, I'm In The Mood For You," "Bob Dylan's Blues," "Blowin' In The Wind," "Quit Your Low Down Ways," "Honey Just Allow Me One More Chance," and "Worried Blues."
• Dylan recorded a version of this song for Broadside, a small but influential folk-music magazine. The precise time of recording has been lost, but it occurred somewhere between October of 1962 and January of 1963.
• The personnel for this recording include Dylan on guitar and vocals, John Hammond on production, and George Knuerr and Pete Daurier on engineering.