Midpeninsula Regional Open Space District, as one of the major land managers of the peninsula, has supported Woodside’s history by allowing the continued use of horses on their holdings. During the early planning process of Thornewood Open Space, the historic Schilling Trail running from the lower portion of Old La Honda Road up to Schilling Lake was a major factor. 

The Mounted Patrol of San Mateo County came into being March 31, 1942, four months after Pearl Harbor Day. San Mateo County had many miles of rough, country and unprotected coastline accessible only on horseback. Military support and protection against subversion were the principle needs that provoked the founding of the Patrol.

For many years, equestrians have ridden through Woodside on the “Center” trail, including through the area affectionately identified on old maps as the “Play Pen”. When the Schwabs announced plans for building a home on their property, there was initial concern about the future of this section of trail.

In Woodside today, we have one of the best equestrian trail systems in the world. They are well designed and maintained. It has taken years to build this system, and the Town Engineer and his Maintenance Staff have done much of the heavy lifting. For over 20 years as Town Engineer, it has been Kent Dewell's leadership and support of the trails that has maintained, improved, and expanded our wonderful trail system. 

Rudy Driscoll exemplifies the caring Woodside resident and equestrian who helps maintain Woodside’s equestrian character by enhancing the Trail System. He embodies the spirit and generous character of early Woodside by providing, building and maintaining a trail linkage that is not only an important connection to other trails, but also enables riders to safely negotiate an area that would otherwise be dangerous.

Signe Ostby and Scott Cook chose to settle in Woodside because of horses. They’ve reared all three children around horses and the younger two are so inspired by the sport of jumping that both have earned national championships! Their love for horses spills over beyond their immediate family, however, to the equestrian community and the Woodside Trails. 

In the late 1800’s, Woodside’s large landowners: the Floods, Folgers and Fleishhackers and others were serviced by the Bear Gulch Water Company. In 1927, California Water Service Company purchased the Bear Gulch Water Company and created the Bear Gulch Water District with over 1200 acres of forested, mountain watershed ranging to elevations as high as 2400 feet.

In 1983, the East Bay Concervation Corps was founded, and is the oldest and largest regional urban corps in California. A national model for other corps and an international model for eductaion, EBCC has changed the lives of thousands of youth and young adults by furnishing job, life, academic, and citizenship skills through environmental-service projects.

Betty Flood moved to Woodside from San Francisco in the early 1940's. A lifelong horsewoman, Betty has been an active supporter and sponsor for Pony Club, Wooodside Junior riders and local events at the old Woodside Play Pen area as well as competitive classes at Mounted Patrol, Menlo Circus Club and Cow Palace shows.

The winding, hilly, single-trail into Huddart Park from Raymunndo Road is a vital link in the Woodside Trails system, yet like an orphaned stepchild it has been passed from on e public guardian to another over the years. In 1982, San Mateo County took over the trail easement on Jim and Janet Estep’s property from the State of California, but soon had to relocate the trail due to erosion.

The first annual Woodside Trails Appreciation Award goes to the founders of the Woodside Trails Club and Mr. Donald Listwin.

In 1922, seven women–Mrs. Selah Chamberlain, Mrs. William Duncan, Mrs. Lawerence Harris, Mrs. Daniel Jackling, Elsa Shilling, Mrs. Nathaniel Messer and Ms. Marjorie Josselyn organized a trail club. the club was limited to those horsemen who could substantiate their horsemanship, had proper trail knowledge and were concerned with keeping the trails open for the use of future riders.