Just the facts: 8 miles, 1500-2000 elevation gain. Paved one lane roads, dirt roads, dirt trails. 4 hours.
I started from my home in South Felton (near Jackson Ave and San Lorenzo Ave) walked up to Scenic Drive. This area is private but lots of folks walk around the one-lane paved roads that meander through the redwoods. Start down Jackson Avenue until it ends and then turn right on Manzanita Avenue (no sign here). Walk a couple of blocks and turn left on McKinley Way and head down the steep road to Gold Ave. Walk the U of Gold Ave to Brookside Way and go left until it ends at Lakeview Dr. Turn left and walk about a half mile to Scenic Drive. Go left up Scenic Drive, a quiet paved road that climbs around a mile. Near the top there is a dirt road with a gate after 100 feet. At the gate a sign tells you that you are entering the upper campus of University of Santa Cruz. This road, named Marshall Trail is not marked from this side but there is a metal gate with a pedestrian walk-through. Walk along Marshall Road until you come to an open meadow at the top and connect to Chinquapin Fire Road.
If you take a left here you will end up in Santa Cruz’s Pogonip Park to Fuel Break Road. In 1999 Santa Cruz, the State and the University joined together to complete a trail from Henry Cowell State park to the Pacific Ocean. I want to hike this trail but not in winter — it crosses the San Lorenzo River in Henry Cowell State Park with no bridge. For this hike you take a right on Chiquapin Fire Road and cross Empire Grade Road and enter Wilder Ranch State Park. Stay on Chinquapin Trail about a half mile until Woodcutter Trail. Take Woodercutter to right and it is a pretty trail that stays near the ridge and ends 1.9 miles at Smith Grade. Back track to your car and feel free to choose different paved roads back (like Willow instead of Lakeview).