The 'Crookedest Street In The World' Is A Famously Scenic San Francisco Spot With Luxe Homes And Cinematic Beauty

If you have ever wandered the streets of San Francisco's beautiful Russian Hill neighborhood, you have probably come across its unmistakable Lombard Street, known for its hairpin turns and zigzags winding through the picturesque sloped neighborhood. Those approaching from the top of the hill usually have an easier time appreciating the view than those starting from the bottom of the steep steps, but regardless of how you decide to approach, crooked Lombard Street is usually a favorite stop on the tourist to-do list.

It's surreal to watch the cars meander their way down this curvy, flower-adorned hill as tourists snap pictures of the lovely hydrangeas and marvel at the sight of the stunning Victorian homes decorating the street. But Lombard Street wasn't always crooked; it used to be a straight street until 1922, when cars became more popular and homeowners found it hard to drive them at such a steep incline. Those who have walked up and down Lombard's winding steps will find it hard to believe there is an even more crooked section of roadway nearby, on Vermont Street, just 20 minutes from San Francisco's iconic waterfront marketplace brimming with artisanal shops and mouth-watering eateries. 

The lesser-known Vermont Street on Potrero Hill is even steeper and more meandering than its Russian Hill counterpart and is becoming more popular as the word spreads on social media of this most "crookedest" street. Comparisons have been made between these two streets, just 3.5 miles apart, and the Department of Public Works in San Francisco decided that Vermont Street is officially more crooked than Lombard Street. Compared drawings of both streets' curviest portions showed more curvature in the selected 100-foot section of Vermont Street than the 100-foot section of Lombard.

While sometimes considered home to the biggest tourist trap in the United States, the sights of world-famous San Francisco are unmistakable, with its nearly vertical street inclines and colorful Painted Ladies-style houses, as seen in the intro of the '80s and '90s sitcom "Full House." This Golden Gate city is no stranger to being in Hollywood films; it has been the backdrop of many famous movies, such as "Vertigo," "Bullitt," "Point Blank," "Pacific Heights," "48 Hours," and the infamous "Dirty Harry" franchise. In fact, the house featured in Alfred Hitchcock's classic suspense movie "Vertigo" was right on 900 Lombard Street. Even MTV's "Real World" reality show filmed its third season here. While Lombard Street has had a lot of exposure in tourist brochures and postcards, Vermont Street isn't as widely publicized and manages to retain a more local, low-key vibe.

"Dirty Harry" fans might recognize Vermont Street from the high-speed chase scene in the 1973 film "Magnum Force," where you can see Clint Eastwood expertly maneuver himself onto this side-winding street in his blue sedan, making dizzying moves as he sideswipes a red car while being chased by a motorcycle cop. The brief scene on Vermont Street is a memorable part of the adrenaline-filled, high-speed chase thrill ride experience created by the film. The street's most recognizable feature is probably the zigzag portion that starts about a third of the way between 20th and 22nd street, where the road makes a tight hairpin turn, and you can see who is coming up and down the hill.

The price of everything is going up these days, but luckily, walking around town and sightseeing is free. Exploring San Fran's gorgeous city streets may reveal little surprises tucked away among its neighborhoods, where you might stumble onto some wild shenanigans, like Vermont Street's Bring Your Own Big Wheel Race. Seeing folks dressed up in wild costumes, peddling for their lives on their Big Wheels, careening down the hills, cornering tight turns, and trying not to wipe out is a hoot. If you are ever near Vermont Street for this yearly event, it's definitely a must-see. Attendees can be seen riding home-made bike rigs, generic plastic tricycles, and even unicycles while sporting some bizarre outfits. This event is free, so just put on a costume, mount your trusty steed (your tricycle), and bring your playful spirit.

Located just 15 minutes away from the historic San Francisco neighborhood famed for funky dive bars, chic boutiques, and bright, lively streets, Haight-Ashbury, the Bring Your Own Big Wheel Race takes place on Vermont Street, between 20th and 22nd streets, next to McKinley Square. The idea of riding down a curvy street on a plastic trike actually originated on Lombard Street, conceived by a man called Jon Brumit.  As you can imagine, Lombard residents did not take too kindly to this spectacle, so Brumit moved his vision to Vermont Street. The BYOBW has been held here every year since 2008. Imagine dozens of costumed competitors barreling down the road, trying not to roll over and crash all over each other; a most spectacular use of the world's most "crookedest" street. Leave it to Frisco folks to come up with such an insane and amazing race.