Authorities said the two were harnessed together in a tandem flight, when they crashed around 12 p.m.
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The park is described by Milpitas fire officials as the fourth most popular spot in the Bay Area for hang-gliding and para-gliding.
Officials said the pair took off from the 1750 launch site, which is the highest launch point at the park.
"People who give tandem rides here are typically instructors, or pretty advanced flyers," a long-time paraglider who asked to remain anonymous told ABC7 News.
He described the hang-gliding and paragliding community in the Bay Area as pretty tight knit.
He said he and others are drawn to the park because it offers several launch points atop Monument Peak to match levels of experience.
However, he noted Monday afternoon's wind would make for a dangerous flight.
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"You could feel the gusts," he said. "That's not very good."
The crash happened around noon. Officials said the woman was airlifted from the scene to Regional Medical Center, and her condition is currently unknown.
Because of the remote location of where the crash happened, responding agencies admitted they ran into some issues early on.
"It's very remote. The terrain is very rugged," Battalion Chief Galahad Zamora with the Milpitas Fire Department said. "It's a single lane road in order to get up to that location. It provided some challenges for our equipment and personnel to get up there and make patient contact."
The news came as a shock to residents who frequent the county park and often catch gliders touching down at a known landing zone.
San Jose resident John Golthy told ABC7 News, "They catch the wind, lift off, fly back down and land in here."
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Information on the man who died, or the woman who was injured has yet to be released.
ABC7 News asked the long-time paraglider, "Are you afraid that you might know these people who were involved?" He took a moment and then replied, "Yeah. Yeah."
Batt. Chief Zamora said incidents in the area are common with hang gliders down or paragliders down.
The paraglider added, "There's accidents, but minor accidents. I'm kind of surprised to hear there's a fatal accident."