article picture

Vermont Street - Is it the Crookedest?

by Susan Saperstein

Did you know that there are two crookedest streets in San Francisco? Yes, you know about Lombard Street--but did you know about Vermont Street on Potrero Hill? Running between 20th and 22nd Streets, Vermont is a 14.3 percent grade and has five full turns and two half turns. But other than those facts, your intrepid editor could not find much else.

In various newspaper articles it is cited as a Works Progress Administration (WPA) building project. However, the WPA was created in 1935, and the San Francisco History Center digital photography collection shows a photo dated from 1928 with the existing curves. Also in the S.F. Public Library is a reference book listing all the WPA projects in San Francisco. The listing includes 130 street, park, and building projects--Vermont Street is not one of them.

Possibly this curved street is associated with the 1000 block of Lombard Street which has eight switchbacks in one block. That block of Lombard was a straight cobblestone street with a 27 percent grade until 1922. Residents approached city engineer Clyde Healy (later coordinator of San Francisco WPA projects, which may be the reason for the erroneous WPA information) to design a way of making the street accessible to automobiles.

In 1977 the San Francisco Board of Supervisors discussed solutions for what had become the heavy tourist vehicle traffic on Lombard Street, with Dianne Feinstein representing the Lombard Street residents.

Discussing the headaches that living on the famed “crookedest street” caused for its residents, the San Francisco Progress reported, “From the way things sounded, Lombard would love to have the name usurped by Vermont.” I looked at the San Francisco History Center folders (several paragraphs, but not much). I looked up several newspaper articles on the 5th floor microfilm (1962, 1977, 1987--they all repeated the same minimal information about the WPA). I visited the Potrero Hill Branch Library and searched the Potrero Hill archives, only to find the same 1987 article previously found in the newspaper microfilm collection.

And I contacted the authors of the Arcadia Publishers’ book San Francisco's Potrero Hill, Peter Linenthal and Abigail Johnston, who said they would love to learn more about the street.

Vermont Street Again

GuideLines put out a request for information on Vermont Street in Potrero Hill as to why this street and Lombard Street are the two crookedest streets in San Francisco. Was Vermont built this way, to mimic Lombard with its switchback curves? Well…..we still do not know why the curves were put in this Department of Public Works project. The 1000 block of Lombard Street, once a straight street, had the curves added in 1922 when the residents wanted to make the street accessible to automobiles. That may remain our best guess. However, City Guide Richard Brandi offered some information:

During the twenties many streets were paved and retaining walls that look similar to the 1928 photo of Vermont Street were built all over town. Instead of using a flush wall, they have a relief or border every several feet and resemble panels. These can be seen all over, from Roosevelt Way to Sunset Heights to Telegraph Hill. Could be Vermont was just one of several such projects as money became available from gas taxes. I assume this was a DPW project under O'Shaughnessy, who helped make SF more car friendly as auto registration skyrocketed during the 20s. I know he instigated building scenic roads, for example. I have never come across any sources to confirm my retaining wall theory, but then again, I haven't looked for it.


This led to some investigation again at the San Francisco History Center, and also another tangent in this story. In the Report of the Bureau of Engineering of the Department of Public Works, City and County of San Francisco, I found some information in the volumes for 1927-1929. These reports document all the city and county public works projects. This includes street widening, paving, grading, and street sign installation. The construction was funded by a bond approved in the election of November 1927.

In the Special Treatment Improvements section of this report for 1927-1928, the photos of Vermont Street taken in 1926 and 1928 appear. These projects included “improvements requiring more than ordinary treatment of local street improvements.” Vermont Street’s grading, walls, and paving were listed as costing $35,000.

Other projects listed in this year were the stairs and retaining wall in Golden Gate Heights, the Montgomery Street retaining wall near Green Street, the Ocean Beach Esplanade, the Broadway Tunnel, and the Hetch Hetchy Aqueduct. It also listed the nascent Mills Field Municipal Airport (later SFO), where it was noted that there were 10,646 flights and landings, and 16,667 passengers.

If you know any more information about this street, please email GuideLines at guidelines@sfcityguides.org.

Credits: San Francisco Chronicle, 11/5/1962 San Francisco Examiner, 1/7/1987 Files in the San Francisco History Center

Thanks to Richard Brandi, author of San Francisco’s West Portal Neighborhood published by Arcadia.

Historic photos courtesy of SF History Center, SF Public Library.

Photo of Vermont St. today courtesy of Liz Einbinder.



article picture

Vermont Street looking south towards San Bruno in 1951.

article picture

Vermont Street north from 21st Street in 1928.

article picture

Vermont Street north from 22nd Street in 1926.

article picture

Vermont Street today with all its plantings.

article picture

Another DPW project in 1928. the Montgomery Street retaining wall.

Send comments and questions to guidelines@sfcityguides.org
Material of San Francisco City Guides. Please give credit to the author and SF City Guides if referenced or reproduced.