Cycling, both road and mountain, is very popular among the sports fitness minded tech workers in the Silicon Valley, and one of the best endurance road climbs begins in Saratoga's Historic downtown. Heading west along Big Basin Way, there's a 9 mile climb along Big Basin Way that winds it's way to the summit of the Santa Cruz Mountains. At the summit, there's the entrance to Castle Rock State Park and nearby a vista point where one can see both the Pacific Ocean, to the west, and the San Francisco Bay, to the east. Big Basin is several miles further along the Summit Road, which is part of Hwy 9, as it winds along the mountain ridgeline. The road is also popular for motorcyclists, and sports car enthusiasts, so cyclists be prepared for not only a hard climb, but one with some traffic risk, particularly on weekends. Fortunately, motorists in this region are quite considerate of the cyclists, in part because the laws against harrassing cyclists are seriously enforced here, but also because of the popular acceptance of road cycling as a fitness sport. If there's a "sag wagon" driver who might risk getting bored, a good strategy might be to drive to the summit parking lot to drop off the cyclists (see image). Allow the cyclists to ride along the ridge and then return by dropping down steep grade of Big Basin Way into Saratoga. Meanwhile, the sag wagon driver can relax by window shopping or sipping coffee at a sidewalk cafe in the four block strip of Saratoga's Historic District, as the cyclists can easily meet at the end of the ride there. Breakaway Bike Shop, which is located across from the Arch Memorial, appears to be a good full service shop, but I did find one serious complaint on-line worth noting...
Up Big Basin Way, at the crossroads with Summit Road, is access to several trails, the most interesting of which is the Bay Area Ridge Trail. The map show in the image here should be taken with a grain of salt in my opinion because I don't really see how this ridge trail can actually be kept contiguous, without urban interruption, around the heavily populated San Francisco Bay Area. Nevertheless in the Santa Cruz Mountains, there is a lot of potential hiking with excellent views of the Pacific Ocean and San Francisco Bay. There are few places to camp though, so figure your logistics carefully if planning a multi-day hiking experience. Incidentally, there is NO SMOKING or campfire building along these trails. The tall grasses and dry forests of California are very suseptible to grass and forest fires. No dogs are allowed on the unpaved State Park trails, and horses are allowed only on specific trails.
Equipment: Better wear your best hiking boots as these mountains are both high and steep--no joke.