EXACTLY 31 years ago this Saturday, the vast concrete paradise known as Winchester SkatePark shut its doors for good. A visionary outpost where future professional skateboarders, including Steve Caballero, honed their talents and learned how to skate safely, Winchester was way ahead of its time.
During its short run from March 1978 to July 30, 1980, other parks came and went, but Winchester sticks in people’s memories, as it put San Jose on the map all across the United States, and perhaps even the world. Alas, after three years, the landlord decided to do something else with the property and Winchester was no more.
This Saturday, a reunion takes place at the Blank Club in downtown San Jose, a rock joint owned by Corey O’Brien, who skated at Winchester as a teenager before going big time himself. Another Winchester regular, Joe Sib, went on to front several bands and will emcee an evening of videos, anecdotes, memorabilia and music from that era.
Operated by Dave Brady and Dan Peterson, who were then in their early 20s, Winchester required everyone to wear helmets, knee pads and elbow pads—always a hot issue, since some folks just didn’t care for safety measures. Even if someone just wanted to take pictures, he had to wear a helmet, since no one knew when an errant skateboard might come sailing out of the pool. But despite the precautions, injuries occurred, and paramedics showed up about once a day.
“We wouldn’t let anyone inside our park, inside the skating area—I didn’t care who you were—if you didn’t put a helmet on,” recalled Peterson. “That was our big thing. We were the only ones who did that. We had the police there a lot, taking people out.”
At that time, skating legend Tony Hawk was already larger than life in SoCal, but according to Peterson, when Tony came to skate the keyhole at Winchester, his dad refused to wear a helmet while watching him skate. He apparently thought the rules didn’t apply to him. If today’s youth soccer coaches think they have it bad when dealing with parents, well, it probably wasn’t any better at the skateparks.
The memories don’t stop there, of course. San Jose native Caballero, still sailing through full pipes at 46, says he owes a lot to Winchester. As a little tyke, he’d already visited a park down in SoCal, but upon discovering Winchester, he came back every weekend.
“I fell in love with it,” he told me. “Every weekend, I would look forward to riding there. It was on my mind the whole week, with school and everything.”
At first, the park was primarily a recreational facility. No one thought about pro careers or sponsorships yet. People just skated, blasted music and had fun.
“For myself,” said Caballero, “it wasn’t in my mind that this would someday become a 30-plus-year career and lifelong achievement, traveling the world, influencing people, inventing tricks, having signature boards and shoes and being in video games. None of this was on my mind at the time. I just loved the way it felt. I loved that I found a hobby that I could progress at, get better and challenge myself. And more opportunities came and it just snowballed into a career.”
Peterson remembers when Caballero first started hanging out: “He would skate eight, nine hours a day. He’d be there at 10 or 11 o’clock, and he’d leave at 9 o’clock at night.”
Ultimately, people continued to get hurt and insurance became a serious problem. After a while, the owners of Winchester and other parks had to piggyback onto the Cub Scouts, requiring everyone who purchased a membership to join the scouts—just so they could fall under the scouts’ insurance plan.
The writing was on the wall towards the end, but for what now seems like a brief moment in time, Winchester SkatePark captured lightning in a bottle, paving the way for everything that came later. The videos, music and memorabilia from that park have defined skateboarding in San Jose to this day.
“It was big,” Peterson said. “But it was going to come to an end because of insurance problems. There was just no way around it.”
Winchester SkatePark Reunion
Saturday, 8pm, free
The Blank Club, San Jose
