"Homeward Bound" was the duo's second single, the follow-up to their enormously successful breakthrough hit "The Sound of Silence". It performed very well domestically, peaking at number five on the Billboard Hot 100, remaining on the charts for 12 weeks. Internationally, the song performed best in Canada, where it hit number two; it was also a top five hit in the Netherlands.
"Homeward Bound" was written upon Simon's arrival in London, England in the spring of 1964. He had previously spent time in Essex, where he became a nightly fixture at the Railway Hotel in Brentwood beginning that April. He was reeling from his brief period in the Greenwich Village folk scene, as well as the recording of his first album with Art Garfunkel, Wednesday Morning, 3 A.M., which he anticipated would be a failure. During this time, he met Kathy Chitty, who was working as a ticket taker at the club. The two hit it off instantly, but it became clear that Simon desired to perform in London, resulting in an emotional farewell. Following a performance in Liverpool, Simon stood on the station at Widnes railway station. He had been missing Chitty's company, and while waiting for the early morning milk train into London, he began to write "Homeward Bound" on a scrap of paper.
Chitty is mentioned in several other Simon & Garfunkel songs, most notably "Kathy's Song" and "America". In their 1970 hit "The Boxer", Simon alludes to a railway station, a possible reference to "Homeward Bound". A plaque commemorating this claim to fame is displayed on the Liverpool bound platform of Widnes railway station. Simon is quoted as saying "[i]f you'd ever seen Widnes, then you'd know why I was keen to get back to London as quickly as possible."