The SCMTA maintains trails at Big Basin and Castle Rock state parks, plus the Skyline-to-the-Sea trail. They also have hikes most Sundays — scroll down to the bottom of the page to find links to photos from their hikes; somebody there knows his or way around an F-stop and shutter setting (I know of these things by rumor and reputation only; I’m a full-automatic guy myself). Membership starts at $7.50.
I bumped into some of these folks one morning while waiting to meet some people from another hiking group. We went to Forest of Nisene Marks State Park. ; they went to Waddell Beach at Big Basin.
This group’s been around since 1969, so they probably remember what San Jose was like before the tech boom turned it into a flattened maze of subdivisions and office parks.