Kerouac’s On the Road had a profound impact on the 1960s’ counterculture. This chapter shows how the ethos of On the Road joined with the ethos of the rock movement that was ushered in shortly after the assassination of President John F. Kennedy in November 1963 by the appearance of The Beatles on The Ed Sullivan Show in February 1964. In addition, the psychedelic rock movement, also inspired by The Beatles, and led by Ken Kesey and the Merry Pranksters, pointed to Kerouac’s On the Road as a clarion call of the 1960s’ countercultural zeitgeist. With unprecedented influence over the youth culture of their times, such rock artists as Bob Dylan, Janis Joplin, Jerry Garcia of The Grateful Dead, Jim Morrison of The Doors, among others pointed to On the Road as a seminal influence on their lives and art. Furthermore, the political wing of the counterculture, including Abbie Hoffman, also viewed On the Road as an inspiring text. This chapter explores the impact of On the Road on the counterculture, despite the novel’s often conservative message, and views it as a bookend to the 1960s’ counterculture.