Backyard Ramps to World Records
Long before skateboarding hit the Olympics, San Jose was already grinding its way into skate history.
This is the hometown of Steve Caballero, one of the most iconic skaters of all time — a pioneer of vert skating and street style who helped define the look, sound, and soul of skateboarding in the 1980s and beyond. Born and raised in San Jose, Caballero turned local parking lots and drainage ditches into proving grounds — and later into platforms for global influence.
But San Jose didn’t just produce legends — it built for them.
In 2008, the city opened Lake Cunningham Regional Skate Park, now the largest skatepark in California. Covering over 68,000 square feet, it’s a concrete playground stacked with the world’s largest cradle, a massive full pipe, vert walls, bowls, and endless street features. It’s more than a skatepark — it’s a magnet for pros, beginners, and entire communities on wheels.
San Jose’s skate culture has always been about creativity, courage, and carving your own path — and it still rolls strong today.