Do you think you know the crookedest street in San Francisco? That would the famous Lombard Street, right? After all, Lombard Street holds the title as “the crookedest street in the world”, and most definitely in all of San Francisco.

Well, you would be wrong. Tens of thousands of people flock to Lombard street every year to see the crookedest street in San Francisco (and possibly the world), and they’re all about 3 miles off from the real thing. Lombard Street is only the second crookedest street in San Francisco. Well, what’s the first you ask?

The real crookedest street in San Francisco is across town in a sleepy neighborhood where very few people know about it. It doesn’t get nearly as much traffic as Lombard Street, and the locals probably prefer it that way. Now granted, Lombard street is far more esthetically pleasing with its brick-lined roadway and colorful flower gardens. But if it’s not truly the crookedest street in San Francisco, then it loses it’s appeal somewhat, don’t you think? And what is this other “crookedest street in San Francisco”? Well, it doesn’t even come close in comparison to Lombard’s street’s beauty with average-looking asphalt road and some decent trees overhanging the street. However, if you want to experience the real crookedest street in San Francisco, all you have to do is head to the Portrero Hill neighborhood, a quiet residential neighborhood on the east side of the city. Now as I mentioned, residents probably prefer nobody knowing about their little city treasure. They like the status quo of their sleepy and quiet neighborhood.

But, this is also great for you because that means you won’t have to wait in line. (Wait, you know there are typically horrendously long lines of cars waiting to traverse down Lombard Street, right?) Tourism officials estimate that 6,000 people daily visit the 600-foot-long street in the summer, creating lines of cars stretching for blocks, especially on weekends. And residents say the scenic street has become more like an overcrowded amusement park than a neighborhood street. They have been calling for years for officials to address traffic jams, trash, and trespassing. Greg Brundage, president of the Lombard Hill Improvement Association stated, “Lines of cars wait to drive on the street, which stops traffic in the city’s Russian Hill area. “The cars really impact the neighborhood because they line up, they back up, they are sitting…”

So in 2019, there was talk in San Francisco of charging people to drive down Lombard, which is a public street. The San Francisco County Transportation Authority had recommended $5 per car on weekdays and $10 on weekends and holidays (residents of the street would have been exempted). But, in October of that year, California Governor Gavin Newsom vetoed a bill that California lawmakers approved in early September. The legislation granted San Francisco the power to establish a toll and reservation system for the block of Lombard Street between Leavenworth and Hyde Streets. However, Newsom rejected the idea, citing social inequity issues and stating “Access to this iconic attraction should be available to all, regardless of their ability to pay.”

But what’s even cooler about this stretch of crooked roadway is that it’s also is host to one of San Francisco’s most iconic events, the Bring Your Own Big Wheels (BYOBW) Race that happens every year (well except for 2020 and 2021, thanks Covid!). The first BYOBW race actually happened on Lombard Street on Easter Sunday in 2000. It was all started by Jon Brummit after he passed out a few hundred fliers. Well, poor old Jon was the only one that day to participate, but after several more years and a lot more fliers, 30 brave souls decided to join him in 2006 in what has since become one of SF’s coolest annual events.


“And then, in 2006 YouTube happened. And that following year it accumulated view after view. At the 2007 gathering, riders and spectators swelled to hundreds.

Well, this did not sit will the residents of this most famous of curvy streets. They took up arms, raising pitchforks and torches (metaphorically of course), and chased Jon and his merry band off, possibly killing the race forever!

So what was Jon to do? The race was in peril! Jon himself was moving out of town and if Lombard was not available, what street could possibly be used?!?!?

And then, someone had a totally non-LSD induced Google map-a-thon search to find a replacement for the fabled Lombard Street…and lo and behold found VERMONT STREET!” –

What’s even more interesting is that this stretch of Vermont Street was designed by the same man as Lombard Street.
But now you no longer have to deal with crowds to drive down the crookedest street in San Francisco. You just have to know where to go for not only the real crookedest street in San Francisco, but also one of the most iconic events in San Francisco. And that is Vermont Street, between 20th and 22nd Streets.
Don’t say I didn’t share TWO cool San Francisco secrets with you.

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