Woodside, CA
San Mateo County

Town Hall in the Charming Town of Woodside

It is said that "You have not really seen Woodside unless you have seen it on horseback." It is a unique, very up-scale Silicon Valley community where many of the locals sometimes kick around town in blue jeans and even muddy boots. It is located in the San Francisco Bay Area, off back from Hwy 280, in San Mateo county, and has enjoyed its equestrian heritage since the 1800s.  In the 1880's prosperous San Francisco families began to establish country estates in Woodside. "It's the kind of place where city folks from Palo Alto, San Mateo, and Menlo Park like to come for breakfast on Saturday morning to soak up the very relaxed, rural, yet up-scale life-style,” remembers Marie Akin-Griffith, avid horse person and once very active bay area Realtor.

Saddle Up in Grand Style

Here you see horses sometimes tied up next to the town's favorite breakfast eatery. Some say it is the kind of town where if you are running for public office, you might well be asked,  "Are you a horse person?" While many of the older generation of equestrians are vanishing, many new Woodside residents most often would rather have a swimming pool or a tennis court than a stable.  However, there is a group of Woodside women working diligently to make sure that the equestrian way of life doesn't become extinct. They have formed the Woodside-area Horse Owners Association, or WHOA.

Actually Woodside doesn’t seem to have changed all that much these past 30 years.  But, there aren't quite as many trails, nor as many horses as there used to be; however,  "the long legacy of horse folks and their equine friends still lives on in Woodside."  The number of horses stabled there has been declining in recent years, going from 765 in fiscal year 2000-01 to 675 in 2006-2007 according to town records. Although the trails are under siege, like many areas close to thriving metropolitan areas, they are in great shape in terms of maintenance “as good as they have been in 20 years” reports the town’s trail committee Chair.

Without the trail system, Woodside would be just a rural Atherton.  Next generation:  Part of keeping Woodside horse friendly is grooming the next generation of horse owners. WHOA members count among their past accomplishments the resurgence of the Woodside Junior Riders, a 10-week-long English riding summer camp.

Woodside Real Estate

Woodside real estate, in land only, is priced at about $1M per acre. Homes pictured below may sell from anywhere from $3M up to $28M, depending on the land, quality and horse and home amenities.

Woodside Area Trails

Woodside's trail system is a patchwork of dedicated trails (within the town where free passage is essentially guaranteed) and the permissive trails (where the right to pass is subject to the permission of the property owner.) As homes change hands, there is an increasing number of new owners who don't want to allow equestrians to use their property, whether for liability reasons, or just simply because they want their privacy.

Sand Hill Trail
The Sand Hill Trail connects with Woodside Town trails. Beginning at Whiskey Hill Road, it turns through Stanford University property along the southerly side of Sand Hill Road following a pleasant, gentle alignment through trees, to its intersection with Portola Road. From there, there is a series of informal trails along Portola Road, maintained by the Town of Portola Valley.

Cañada Trail
The Cañada Trail intersects the Crystal Springs Trail about one-half mile south, near I-280 overpass across Cañada Road. It then follows the westerly side of Cañada Road into the Town of Woodside, where it connects to Woodside Town trails at Woodside Road.

Skyline Trail - Wunderlich County Park
The Skyline Trail originates at the northwesterly corner of Huddart County Park, and connects to private trails running northerly along Skyline Boulevard. The public portion runs easterly of Skyline Boulevard, through Huddart Park, to Kings Mountain Road. There, it crosses Kings Mountain Road and passes into the California Water Service Watershed. Here, it follows the northerly boundary of the watershed through a fenced easement, turning southerly and paralleling Skyline Boulevard on the easterly side, for about 4.5 miles. After leaving this easement through the watershed, it passes through Wunderlich County Park, then out to Skyline Boulevard near Skylonda, and its intersection with La Honda Road. As it passes through Wunderlich, there's an opportunity to connect with the Bear Gulch, Alambique, and Woodside Town Trails.

NOTE: Above information gathered my various newspaper articles and from my own experience in visiting, eating, and riding in the Woodside area. --Marie Griffith

Email Us for a referral of an
Experienced Equestrian Property Specialist who lives in
to answer your questions and furnish you a list of properties

Horse Properties
Horse Properties
Horse Properties
COMMUNITIES  Neighborhoods

Copyright 2009. Marie Griffith, Garden Valley Enterprises. All rights reserved.
Disclaimer: All information deemed reliable but not guaranteed and should be independently verified.











Hit Counter