I was looking for information on the Last Chance properties near Big Basin and I came across this gem of a website from Ray Hosler. There are quite a few pages which document these legendary "Jobst" rides from the early 1980's. A bunch of riders including Tom Richey would do epic all day fire and dirt road explorations in the Santa Cruz mountains with their road bikes.
Check out the slide show which documents 26 years of riding in the Santa Cruz mountains. It's neat to see some of the vistas and places that these guys took their road bikes. There are all sorts of neat nuggets of history if you poke around the site including the train tunnels in the Santa Cruz Mountains.
No helmets, CamelBaks or suspension. Definitely old school. These guys were the pioneers of the sport.