Grass Mountain Trail

Grass Mountain Trail is a 5.2 mile out and back trail located near the towns of Los Olivos and Santa Ynez. Depending on the season, the trail may feature beautiful wildflowers which adds to its popularity. The trail is primarily used for hiking and rated as difficult; dogs on leash are also able to use this trail.

Starting off easy, this trail steadily increases in difficulty until the final mile directly up the side of the mountain to the peak. It is not the highest mountain in the area but has commanding views over most the surrounding area.

Midland School Trails

The Grass Mountain hiking trail is part of The Midland School trails, a private trail system opened to the public through the generosity of the school. Hikers must fill out a permit and parking pass at the trail head, where permit boxes are located.

Finding the Trailhead: Shortly after passing what was formerly Michael Jackson’s Neverland Ranch, as you ascend Figueroa Mountain Road, you will cross over a cattle guard. Parking should be available on the right. Cross the street and find the trailhead where the permit box is located.

Note: The Midland School Trails are subject to closures. Visit www.midland-school.org to learn more. See this map for more information regarding the Midland Trails and for further contact information: https://sbtrails.org/maps/midland/Midland-Trail-Map-2016.pdf.