In 1960s historiography today, the expression ‘Summer of Love’ is used in three senses. It refers generally to the explosion of psychedelic sounds, images and lifestyles in that decade. It is also code for the overall phenomenon of Haight-Ashbury between 1965 and 1968. Specifically, and more accurately, it applies to the summer of 1967 in the Haight-Ashbury district of San Francisco. While the multiple meanings all carry weight, too often that first general sense of the Summer of Love shields a dialectic of hope and despair behind a banner of optimism and dreams. To put it more bluntly, the hippie experiments of the 1960s were full of utopian promise, while the Summer of Love actually spelled the end of that particular vision in Haight-Ashbury. This is a paradox rarely explored.