[1] Once a portion of Octavia Street alongside shadowy, fenced-off land beneath the elevated U.S. Route 101 roadway, Octavia Boulevard was redeveloped and redesigned upon the recommendation of a "Central Freeway" planning committee representing a broad array of neighborhoods, including the surrounding Hayes Valley and Western Addition, the Richmond District, Pacific Heights and the Sunset District with representatives appointed by Mayor Willie Brown and the Board of Supervisors and led by the Planning Department of San Francisco.

Elements of the San Francisco General Plan were consulted for issues such as urban design, transportation mobility and congestion management, community safety and historic preservation, along with the evaluation of the impacts following the recent removal (1991) of the elevated Embarcadero Freeway and the revitalization of the Embarcadero as a surface boulevard complemented by an extension of the Muni Metro light-rail transit subway.

Mark Jolles, a local resident attending the meeting, was concerned that the committee was only considering two alternatives to mitigate the removal of the elevated freeway.

For grade separated freeways, due to limited access to local streets, traffic cannot readily adjust during peak periods.

Blight was caused by the double-decker concrete behemoth overwhelming street life with noise, dust, and shadows.

When a block of public housing was being replaced at Webster a better connection from that divided street to Oak and Fell could be added.

This included a future branch of the Market Street F Line west as a couplet along Oak and Fell towards Golden Gate Park.

During this time, the planning services of Allan Jacobs, the former Planning Director and Chair of the UC Berkeley College of Environmental Design and his business partner and UC Berkeley Landscape Architecture professor Elizabeth MacDonald, whose academic studies of landscaped, multi-lane surface roadways were being compiled for publication as "The Boulevard Book" (2002), were engaged.

This led to a proposal for rebuilding Octavia Boulevard without the freeway structure, which was concurrently reviewed and ultimately deemed "acceptable" in traffic carrying capacity as an alternative to a freeway ramp by Caltrans, which informed the endorsements of the civic design think-tank SPUR, both the Planning and the Parking and Traffic Commissions, and Mayor Willie Brown in his "State of the City" address in October 1997.

The ballot measure, which did not include references to the progress and design of the replacement surface boulevard, was passed by the voters in November 1997.

Members of the Central Freeway planning committee, led by community activists Robin Levitt and Patricia Walkup, regrouped immediately to draft another ballot initiative (Proposition E) calling for the surface boulevard as the preferred alternative to rebuilding the elevated structure north of Market, supported by the urban design benefits of the boulevard and its acceptability per Caltrans' standards in carrying traffic.

Octavia Boulevard is four blocks long from Market to Fell Street, containing multiple lanes that separate local and through traffic.