The trail begins on Bollinger Canyon Road behind Windemere Ranch Middle School. Travel south east on this moderate trail with beautiful views behind Six Pillars Park and towards the Tassajara Ridge Trail. Views include the rolling hills of the valley, Camp Parks and various wildlife including jack rabbits. The trail alternates between paved and earthen trail consisting of a mix of grass and dirt with slight to moderate increases and decreases in elevation. There are various access points throughout the trail within the neighborhoods at Stonehenge Way and Holbron Way. The Rolling Hills Trail is suitable for walking, running and cycling.  Hikers may encounter cattle on this trail, please review cattle grazing area safety tips in the San Ramon Trail System Rules & Etiquette.