The broad Olema Valley trail can be biked in either direction and tackled in sections. This description starts from the Five Brooks trailhead. Round the bird-filled pond at the Five Brooks trailhead and cover mostly level ground next to Olema Creek at the base of a steep hillside. Cross a bridge set into a deep canyon and prepare for a strenuous climb. The grade mellows a bit, and soon you reach the intersection with the Bolema Trail, knowing that all the hard work is over.
Continue straight on the Olema Valley trail, gradually losing all that hard-won elevation through a series of enjoyable rolling sections through wooded areas and clearings. After the junction with the Randall
Spur (and associated Randall
Trail across the highway), the trail twists back uphill for a brief section before more level terrain prevails. After a meadow with views of the surrounding hillsides, you must ford Pine Gulch Creek. There is no bridge here and water can sometimes reach knee high in the winter and spring. From here to the trail terminus, the ground is level but often overgrown with brush, stinging nettles, and poison oak, so long pants are recommended. There is one final creek crossing after passing the junction with Teixeira Trail.