(Originally written in the early 2000's, rescued from the Internet Archive, and reposted here for posterity.)
In May 2002, a friend and I took our bikes up to the Canada Road Bicycle Sunday event. Every Sunday the county closes off a 4.5 mile stretch of Cañada Road for bikers, rollerbladers, runners, etc. That was really quite cool, although it was quite windy. The road goes along very pretty hills, Crystal Springs Reservoir, the Pulgas Water Temple, and the Filoli Estate (remember Dynasty?). We continued beyond the southern road closure boundary and biked to the little town of Woodside, which made the trip14.6 miles roundtrip. And there is plenty of parking areas for cars.
Castle Rock State Park
A friend and I went hiking in April 2002 at Castle Rock State Park. My friend knew where the trail was, so he was the leader. The Park is located hear Hwy 9 and Skyline Blvd. There's plenty of roadside parking, and the trail entrance has a restroom. There are several trails that you can choose from, but we went on the Skyline trail, which goes on for many miles. We hiked for 3 hours, at about 4 miles and hour, so I think we covered between 10 and 12 miles, round-trip. About a quarter of the way along the trail is an observation deck overlooking a beautiful waterfall. Rock climbers rappel down to the bottom of the waterfall from the observation deck, and then climb back up. About three-quarters of the way is the campsite registration area, with another restroom, and map of the trails. At the end of the trail is a "private property" sign, and a large barking dog guarding the residences. The views are beautiful - you can see all of the valley (pictured above) between San Jose and the Santa Cruz Coast (with ocean in the distance). The trail is covered with odd rock formations that make hiking interesting, and somewhat painful on the ankles. There are very primitive campsites along the trail (primitive meaning "relatively flat pieces of land").
Coyote Creek Parkway
This is a 13.7 mile paved multi-use trail that follows Hwy 101 near Blossom Hill Road. The trail runs along Coyote Creek from Coyote Hellyer County Park to just north of Anderson Lake County Park. The trail is secluded by trees and brush, but close enough to the freeway to hear the cars. You can park at Coyote Hellyer County Park for $4, or just park at one of the access points near Monterrey Road for free. I frequently park at Shady Oaks Park, just off Blossom Hill Road. Some parts of the trail, particularly just south of El Parque de la Raza de Paz, are quite bumpy and would not be good to bike on. The rest of the trail is well paved, smooth, and not very hilly. As you go south on the trail, you will pass the airstrip along Highway 101 where model plane enthusiasts fly their planes (they also have a restroom there). It's neat to watch those planes flying.
Los Gatos Creek Trail
Over seven miles of mostly flat, paved trail for biking, walking, jogging and skating. Stretches from Willow Glen and Campbell (Leigh Ave & Willow Street) to Los Gatos (Vasona County Park and downtown), and then continues unpaved to Lexington Reservoir. Bridges and underpasses mean the trail almost never crosses a street. The trail is well maintained, and dogs must be kept on leashes. Emergency call boxes every 1/2 mile on most of the trail. Access from nearly any road crossing the trail, but best parking is probably near the Campbell Park (Campbell Avenue), the percolation ponds at Los Gatos Creek County Park, off of Dell Avenue, and at Vasona County Park.
Vasona Park consists of Lake Vasona and 151 acres of parkland near Los Gatos. The park is at the southern end of the Los Gatos Creek Trail. The trail runs along the east side of the lake, and loops around to the west side, but does not make a full circle. South of the lake, the trail divides and reconnects near the miniature train station and carousel, where it then continues through the town of Los Gatos and up to the Lexington Reservoir. The trail is paved (except the Lexington Reservoir leg), and the terrain is level. Access the park and the trail from Blossom Hill Road or University Avenue. You can also access the trail from Lark Avenue, although there is no parking along Lark. Jogging or biking around the lake can be difficult because of all the picnics going on and kids on bikes, but the section between the park's train station south to Los Gatos is very peaceful and serene as it winds through the woods.
The paved portion from Campbell to Los Gatos is mostly flat, but once you get past Los Gatos headed up to Lexington Reservoir, it's mostly uphill, and so steep at some points that you have to walk. It's approximately 20 miles round-trip, from Campbell to the Reservoir and back.