San Francisco’s Most, or Second-Most, Crooked Street

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San Francisco’s most, or perhaps second-most – depending on whom you ask – crooked street was a straight, unpaved road one hundred years ago.  Vermont Street’s serpentine pathway was constructed in the 1930s as a Works Progress Administration project. The argument over which street – Vermont or its world-famous cousin, Lombard – is the most crooked has gone on ever since.

Perhaps the earliest record of the curve competition appeared in a 1962 article by Joseph Sheridan, published in the News Call Bulletin, which reported that roughly 40 Hill residents wanted to make Vermont Street as famous as its cousin.  The residents dedicated three weekends in a row to installing sprinkler and irrigation systems, landscaping and generally beautifying their most-crooked-street, planting some 200 or more trees and plants, including junipers, Veronica, pines, Escallonia rubra and Diosma, some of which are still growing today. 

Lombard Street was built in 1922, according to a 1977 SF Progress story by Carol Kroot.  Vermont Street has five curves compared with Lombard’s eight. Lombard Street features an 18.18 percent grade, according to a 1977 San Francisco Chronicle story by Peter Stack.  Vermont Street’s grade, or steepness, is 14.3 percent, about four percent less steep than Lombard.

Also in 1977, City officials decided to make Vermont Street one-way southbound, a decision that’s lasted until this day. A sign at the top of Vermont Street, where the curves begin at McKinley Square, states: “trucks not advised.”  Another placard indicates that trucks weighing more than three tons are prohibited. A 1940s photograph shows a car driving northbound on Vermont Street’s curves from a straight stretch of road south of 22nd Street, before the freeway was built.

Houses lines both sides of Lombard Street, while Vermont Street has homes only on its east side. The west side features views of U.S. Highway 101 and Zuckerberg San Francisco General Hospital.   Although previously planted Escallonia rubra has white, pink and red flowers, nothing was blooming on Vermont Street last month.  Pines and other evergreens loom large, and in places create a canopy for drivers. Shorter trees and bushes line the curves. 

Traffic has been a concern for years for Lombard Street residents, who have complained of the noise and damage done by vehicles crashing into their homes. Lombard Street residents also complained of traffic of a different sort. The Bring Your Own Big Wheel Race started in 2000 on Lombard Street, but residents complained that the bright colored plastic toys stopped traffic and damaged shrubs. Founder Jon Brumit took the race to Vermont Street, where since 2008 it has been a hit with riders and residents.

History has nothing to say about Hill residents’ traffic concerns, at least as it relates to Vermont Street. Less than a half-dozen automobiles traveled down the street in 30 minutes during a late-morning in early July. The traffic was so sparse someone could walk down or up the street without fear of being hit.

Those who argue that Vermont Street is the most serpentine in the world, or at least in the City, base their claim on the tightness of its curves. In photographs, Vermont Street’s curves appear tighter than Lombard’s. 

When asked for a verdict on the contest, San Francisco Travel spokeswoman, Laurie Armstrong, cited a 1995 edition of the San Francisco Almanac that states that Lombard Street is the most crooked.