Hippie Hill has been a part of San Francisco’s history, namely the Summer of Love, in 1967, a large counterculture movement that partially took place on the hill. With its close proximity to Haight Street, the main site of the Summer of Love, the movement often overflowed onto the hill. During this era, people gathered in the area to connect with one another through many activities, including the playing of music, consumption of LSD and marijuana, and expression of hippie ideals. 

Through this movement, music became to have its own history on the hill as well. Musicians and bands such as Janis Joplin, the Grateful Dead, Jefferson Airplane, and George Harrison all played free shows here.