The present day Haight-Ashbury area is situated on land that was first inhabited by the Ramaytush Ohlone people, a network of Native American tribes that lived in the San Francisco Bay region.

The present day Haight-Ashbury area stayed largely unsettled due to its inhospitable topography of sand dunes and was mostly limited to cattle grazing.

Before the completion of the Haight Street Cable Railroad in 1883, what is now the Haight-Ashbury was a collection of isolated farms and acres of sand dunes.

The cable car, land grading and building techniques of the 1890s and early 20th century later reinvented the Haight-Ashbury as a residential upper middle class homeowners' district.

[20] The cable car lines and improvements in land grading and building techniques enabled the development of a residential area that catered to upper middle class homeowners.

Residents with enough money to spare left the declining and crowded neighborhood for greener pastures within the growing city limits, or newer, smaller suburban homes in the Bay Area.

Deferred maintenance also took its toll, and the exodus of middle class residents to newer suburbs continued to leave many units for rent.

[29] Another well-known neighborhood presence was the Diggers, a local "community anarchist" group known for its street theater, formed in the mid to late 1960s.

The Monterey Pop Festival in June further cemented the status of psychedelic music as a part of mainstream culture and elevated local Haight bands such as the Grateful Dead, Big Brother and the Holding Company, and Jefferson Airplane to national stardom.

[33] The Summer of Love attracted a wide range of people of various ages: teenagers and college students drawn by their peers and the allure of joining a cultural utopia; middle-class vacationers; and even partying military personnel from bases within driving distance.

[31] On October 6, 1967, in Buena Vista Park, those remaining in the Haight staged a mock funeral, Digger happening, "The Death of the Hippie" ceremony.

[36]Ron Thelin stated that Haight-Ashbury was: Portioned to us by the media-police, and the tourists came to the zoo to see the captive animals, and we growled fiercely behind the bars we accepted, and now we are no longer hippies and never were.

[37]After 1967, Haight-Ashbury saw a rapid departure of residents due to overcrowding, high crime rates, and drug abuse, yet certain institutions such the Free Medical Clinic remained.

The HANC lobbied against commercialization, in particular opposing urbanization and developmental projects aimed at bringing chains and multi-unit housing developments.

[41] Grassroots organising and local activism in Haight Ashbury solidified itself in the political culture and legacy businesses including bookstores, boutiques and cafes marketed the essence of the sixties counterculture.

Many gay bars, businesses and clubs shut down and were replaced with new businesses less catered to gay audiences, but existing cooperative medical and political establishments such as Haight Ashbury Free Clinic were instrumental in ensuring access to medical aid through their needle exchange program that decreased the spread of HIV/AIDS.

[46] It has become a hotspot for tourists and locals alike, with walking tours, city-sponsored projects and boutiques or coffee shops tied to the counterculture ethos.

Gentrification has strongly impacted Haight-Ashbury and led to increased property values and rents, displacing long-term residents and hindering affordable housing efforts.