A town of wide open spaces.
City Limits
A small town with big lots, epic estates, and a popular network of horse trails, the Town of Woodside is one of the wealthiest communities in the United States – an exclusive list that also includes San Mateo County neighbors Atherton, Hillsborough, and Portola Valley.
Woodside has boasted a number of rich and famous residents over the years, including singer-songwriter Joan Baez, tech giants Larry Ellison and Steve Jobs, 49ers Hall of Fame Coach Bill Walsh, and award-winning actress Michelle Pfeiffer, along with numerous Silicon Valley CEOs, venture capitalists, business magnates, and – currently – 6 billionaires!
Woodside is also home to a number of open space preserves, including the Purisima Open Space – part of the Midpeninsula Regional Open Space District – which allows both horseback riding and bicycling.
Woodside By the Numbers
Population: 5,550
Median age: 50.3
Median household income: $250,001
Median property value: $4.7M
#BIKELIFE
Speaking of bikes, Woodside is a popular destination among local cyclists. The most used road routes include Old La Honda Road, King's Mountain Road, Cañada Road, Southgate Drive, and Highway 84. For mountain biking, there's Skeggs Point (pictured) off Skyline Boulevard.
Location Scouting
Many popular movies have been filmed in the spectacular homes and estates of Woodside, including Bicentennial Man starring Robin Williams. The Filoli Estate (see below) was featured as an exterior on the TV show Dynasty, as well as in the films The Wedding Planner, The Game, Lolita, George of the Jungle, Heaven Can Wait, and Harold and Maude. The musical Rent also has a scene filmed inside Filoli.
Where to go
Filoli Estate – Filoli is one of 27 sites owned by the National Trust for Historic Preservation, a privately funded, nonprofit organization that works to save America’s historic places. Filoli Center, a local nonprofit, has full management responsibility for the property, which is home to beautiful gardens, sprawling grounds, and classic architecture. In addition to movie shoots, the estate also hosts weddings and private events.
Huddart Park – The forested slopes and steep, cool canyons of Huddart Park are located within easy reach, a few miles west of Highway 84. Barbecue pits, a playground, grassy meadows, and hiking and riding trails make Huddart Park a great place to spend a day with the family.
Djerassi Ranch – Djerassi features an internationally-recognized Resident Artists Program, situated on a unique hillside property. The program aims to preserve the land and use their facilities wisely and efficiently for maximum benefit to the artists, while leaving the least impact on the environment.
WHERE TO EAT, DRINK & HANG
Buck’s of Woodside – Owner Jamis MacNiven left his career in construction to open this restaurant in 1991. By 1995, when the dot-com boom began, Buck's had become a hotspot for Silicon Valley power lunches – and breakfasts. This is likely due to its close proximity to Sand Hill Road, home to venture capitalists.
Alice’s Restaurant – Sometime during the 1960’s, this restaurant was bought by Alice Taylor, who renamed it after herself and the now famous Arlo Guthrie song. A world famous stop for motorcyclists, hikers and tourists, Alice’s has been family owned and operated for nearly 50 years.
The Village Bakery – If you’re in a rush and need something super-fast, or if you're looking for something a little more casual, this bakery offers a bunch of grab-and-go selections, including pastries, coffee, fresh-pressed juices, sandwiches, and salads.
