Equestrian culture, natural scenery, and town-and-country lifestyle at their finest
In the 1830s, Woodside was developed into sawmills that supplied redwood to San Francisco. Gradually, it turned into ranches and vineyards. In the 1880s, wealthy San Franciscans took the stagecoach service south and began building their country houses here. One example is the 1915 Filoli estate. It features a Georgian-style mansion and botanical gardens on 16 acres. While the post-WWII building boom brought hundreds of new houses, Woodside has kept its rural ranch-style setting. Even the downtown feels like a small Western town with only a few shops and a post office.
However, Woodside is one of the most exclusive neighborhoods in Silicon Valley and one of the wealthiest in the world. Though you may find some of the older ranch-style homes from the 1920s, there are plenty of modern and lavishly designed mansions. Large country-like estates are surrounded by nature preserves, immaculate tree-lined streets, and horse trails. Many residents own horses they keep and care for on their property. Some have spacious farmland for their horses to roam free, while the city is responsible for maintaining the network of trails in the community. This equestrian culture gives Woodside a unique appeal. Famous residents have included Michelle Pfeiffer, Shirley Temple Black, and Oracle co-founder Larry Ellison.
Woodside has a distinct old country-western vibe. Residents embrace their rural lifestyle, riding their horses through the woods and around the community. They also like to take advantage of the wide-open green spaces in the area, many with third-generation redwood trees. On the weekends, bikers and motorcyclists cruise along popular routes along Cañada Road, Skyline Boulevard, and Highway 84.
Downtown Woodside only has a few restaurants. Buck’s Restaurant is a quirky restaurant serving American fare and is loved by the locals. It’s also rumored to be a favorite by resident venture capitalists working out negotiations.
The Firehouse Bistro offers modern French comfort food using seasonal ingredients. The Village Bakery is a restaurant and bar great for brunch or date night. For fine dining, The Village Pub serves gourmet American dishes and a selection of wines. It was awarded a Michelin star for “high-quality cooking.”
For a social night out, the Pioneer Saloon has karaoke and live music. For groceries, Roberts Market and Liquor has specialty foods, fresh produce, meats, and wine. There’s a hardware store and a popular home and garden store, Emily Joubert. You can also check out the nearby Menlo Park Farmers Market on Sundays for fresh produce and live music.
Woodside was made for nature lovers. Thornewood Open Space Preserve has a beautiful lake, hiking, and horse trails. The Horse Park sits on 272 acres and is complete with horse stables, obstacle courses, and exercise and practice trails. Huddart Park is 900 acres of dense forest. It offers hiking and riding trails, picnic areas, and an archery range. The Purisima Creek Redwoods Open Space Preserve is a 5,412-acre preserve with towering redwood trees and a meandering creek. It has spectacular views of the coast and Half Moon Bay.
Art lovers enjoy Djerassi Ranch. The private 580-acre ranch has an artist-in-residence program that started in 1979 and displays sculptures it has collected from its artists throughout the years. They also offer sculpture hikes to visitors. For golf enthusiasts, Menlo Country Club is a members-only 18-hole golf course with event facilities.
Woodside is served by the Woodside School District, the Sequoia Union High School District, and the Cabrillo Unified School District.
Together with his wife and son, the Buljan Group has grown as a commanding force in the local real estate realm over the years selling every major landmark property in the community.
