Woodside & Portola Valley
Photo by: Kasimira Photography
Woodside and Portola Valley sit side-by-side next to Interstate 280, both offering Bay Area residents a rural retreat in the heart of the Peninsula. What makes these two towns so special is how you can have an estate in the woods, surrounded by nature—yet just west sits the high-tech and venture capital firms of Menlo Park and Palo Alto. San Francisco is a quick drive to the north and San Jose and the rest of Silicon Valley are to the south.
They also share a really unique equestrian culture. When people think about the Bay Area, they probably don’t think about neighborhoods full of farms or people riding horses down the street. But that’s exactly what you will see in these two towns.
Woodside:
Woodside gets its name and its origin from the redwoods that grow here. It was these redwoods that built many of the first homes in San Francisco and helped rebuild the city after the 1906 earthquake. Like many of the Peninsula’s wealthy suburbs, Woodside was populated in the 1800s by wealthy San Franciscans who wanted an accessible country estate. A stagecoach stop made this possible. Some of the first homeowners here were James Folger (think coffee), August Schilling (spices) and C.F.A. Talbot (lumber).
It was after World War II that the area saw an influx in new development. Large estates were subdivided and by 1956 it became the incorporated Town of Woodside. This choice to incorporate is why Woodside still feels like a rural retreat today with its vast wooded areas, large lots, equestrian culture and limited commercial zones. You really can’t get this same vibe anywhere else in the Bay Area—it’s like California meets the old west.
The businesses that are in town carry that charm and the history of the area. The Pioneer Saloon looks like it could be a movie set for an old western and often has live music or open mic nights. Roberts Market still maintains some of its general store roots—with all the modern day groceries you need—plus a tack and feed store. Buck’s of Woodside is not just a restaurant but a museum of wacky artwork and collectibles, popular with families, venture capitalists and even celebrities. One Michelin-starred restaurant, Village Pub, offers fine dining. Alice’s Restaurant is another legend at the corner of Skyline and La Honda Road, it offers casual cuisine in a rustic cabin and is a popular stop for motorcyclists.
The town has its own one school district with Woodside Elementary School (TK-8th) which sits on a 16-acre campus. A private preschool is also located on the same campus. Some students may attend elementary or middle school in the Las Lomitas, Redwood City or Portola Valley school districts. Most kids will then attend Woodside High School (part of the Sequoia Union High School District).
Even remodeled homes often maintain the rustic traits of the original cottages or estates built in the area with wood siding, shingles and landscaping that’s often left to nature’s way. There are a lot of private gravel roads, rambling fenced-in lots and barns housing horses, sheep, chickens and pigs. The town maintains a series of horse trails, and you’ll see horse-crossing signs on the streets. Bicyclists and hikers flock to the area on weekends. Wunderlich Park is one of the many options with trails and historic Folger Stable, which offers free tours and has a Carriage Room Museum.
Neighborhoods to the east of 280 include unincorporated Emerald Hills, Woodside Hills and Woodside Heights. Woodside Glens and Mountain Home Road are west of 280 and close to the commercial businesses in town center. Getting even more into a rural remote feel, you’ll find Family Farm/Hidden Valley, Skywood/Skylonda and Kings Mountain scattered in pockets to the west.
One of my favorite places in Woodside is the Filoli estate and gardens. It’s one of the town’s early country estates, built for the Bourn family (owners of Empire Gold Mine and Spring Valley Water Company) in the early 20th century. The property consists of 654 acres and the country home and beautifully manicured formal gardens take up 16 of those acres. It’s worth touring any time of year or visiting during their holiday festivities.
Woodside continues to be home to some notable names. Larry Ellison (Oracle) spent $200 million renovating a 23-acre Woodside estate into a 16th-century Japanese-inspired compound with a man-made lake, tea house and koi pond. Michelle Pfeiffer and David E. Kelley recently sold their Mediterranean-style home with equestrian facilities for $22 million. Steve Jobs owned the historic Jackling House, which he tore down (to much controversy) and was in the process of replacing at the time of his death.
Portola Valley:
Before there was modern day Portola Valley, there was the logging town of Searsville alongside Sand Hill Road. It existed from the 1850s to 1891 and was built to accommodate men coming into the area to cut down redwoods for all the building happening in San Francisco. When the redwoods were gone, Searsville was abandoned. The inventor behind SF cable cars, Andrew Hallidie, had a large estate estate running west from Portola Road all the way to Skyline. He offered up a section of land for a new school, and the town of Portola Valley eventually developed around it.
It was a mix of small farms, summer cottages and some large estates—and much like Woodside, popular with wealthy San Franciscans looking for a country escape. In 1964, residents voted to incorporate to maintain control of their town’s housing and development. The result of that vote is the Portola Valley we know today. It still has a rural feel with 1,900 acres of open space, low-density housing and limited businesses. Though there are similarities, it doesn’t feel as western as Woodside and you’ll see a lot of mid-century modern influence in the architecture.
Photo by: Kasimira Photography
Alpine Inn recently underwent a renovation and is the most historically interesting business in the town. It’s the second oldest continually operating tavern in California, starting out as a gambling house named Casa de Tableta in 1852. The remodeled beer garden is a mix of nature and big screen tvs, making it the perfect place to grab a beer, a burger and watch a football game. Portola Valley has a really unique town center that combines old and new. The “new” was officially opened in 2008 with a library, community center, recreation fields and Town Hall. There is also the former one-room schoolhouse built in 1909 that is now used for town council meetings and is on the National Register of Historic Places. Down the road you’ll find more shops at Village Square, including a veterinary hospital, feed center and saddlery to serve the equestrian community. Off Alpine Road there is the Ladera Country Shopper with a Bianchini’s Market and some varied restaurant options like Koma Sushi, Old Port Lobster Shack and Portola Kitchen.
The Portola Valley Elementary School District consists of Ormondale (K-3) and Corte Madera (4-8). The public high school is then Woodside High School. There are two private schools in town: Woodside Priory, a boarding school for grades 6-12 and Woodlands School for PK-8.
Westridge is the northernmost community and has strict housing requirements that promote seclusion. Lots are 2.5 acres minimum, many residents have horses and most houses are tucked back and not visible from the street. Central Portola Valley is the largest community near the most businesses and community amenities. Woodside Highlands and Brookside Park are very small communities off Portola Road. Portola Valley Ranch is a planned community of cul-de-sacs with a private community center. You’ll find some of the newest homes in the small community of Blue Oaks which was developed in the past two decades and consists of 2-acre lots.
Ladera is an unincorporated community of just 0.4 miles along Alpine Road. It’s outside the northern border of Portola Valley with a similar feel (though under the Las Lomitas School District). Similarly, Los Trancos Woods and Vista Verde, are just outside the border but to the south. This area was once a community of small, 400 square-feet-or-so cabins but as time went on, those original cabins have been replaced by much larger homes. Explore the area though and you’ll still feel that wilderness vibe.
While Portola Valley still has its share of small cottages and rustic farm properties, there are also plenty of elaborate estates owned by Silicon Valley elite. Sun Microsystems co-founder, Scott McNealy initially put his 12,000+ square-foot mansion on the market for $100-million before dropping it to $53.888-million. Real estate billionaire, John Arrillaga, and Nike CEO, John Donahoe have also called Portola Valley home.
The San Andreas Fault runs under the town and there is even a short 1.4 mile loop trail with educational posts about earthquake activity.