Woodside is packed with natural beauty, historic sites and miles of trails for hikers, bikers and horseback riders. It’s usually a sunny place to get a break from coastal fog, but there’s also shade under the redwood and oak trees that cover this wealthy town in San Mateo County at the base of the Santa Cruz Mountains.
Visitors can bask in the sunshine in Woodside’s very small downtown, which is easy to access via the Woodside Road exit from Interstate Highway 280. Head west until the road intersects with Cañada Road to reach the heart of it. You’ll pass some old wooden buildings that give Woodside a western feel.
The best-known restaurant is Buck’s of Woodside, located inside a shopping center at 3062 Woodside Road. Look inside for the old paintings, personalized license plates, bronzed baby shoes, model boats and airplanes that make it hard not to enjoy. Buck’s serves three meals a day and is a popular diner for Silicon Valley venture capitalists and tech entrepreneurs. On the weekend, it can be full of families and bicyclists, who also spill over into the Village Bakery next door. Both eateries offered outside seating areas in the parking lot during the pandemic, and a lively scene remains. Bicyclists also congregate on the sidewalk across the street at the town’s main store, Robert’s Market and delicatessen.
After a meal, it’s easy to walk or drive to the one-acre Native Plant Garden at 3140 Woodside Road, located behind the Woodside Library. The garden was established in 1970 and has a redwood grove, an oak woodland area and benches to sit and enjoy the native plants. Poems about nature are placed on signs throughout the park. The garden can be visited whenever the library is open.
Woodside is located close to county parks full of redwood trees, including Huddart and Wunderlich. Huddart Park, located about three miles from town, charges $6 for daily parking. There are lots of trails here across the hilly 974 acres in the park.
Wunderlich County Park is four miles from Buck’s on Woodside Road. It has free but limited parking, which is often full on weekends. Wunderlich contains one of Woodside’s top attractions, known by the grandiose name of the Folger Estate Stable Historic District. It features a working stable built by the Folger coffee family of San Francisco for their Woodside country home in 1905. The main stable looks big enough to live in, but hey, it’s for horses. It was designed in a French Baroque style by Arthur Brown Jr., who later designed such San Francisco landmarks as City Hall and Coit Tower.
The stable also contains a museum that is open on weekends, and a restored carriage house and a blacksmith barn. A fundraising campaign is currently underway to restore the Dairy House on the site, built out of stone in 1874.
Wunderlich Park has a thriving equestrian scene, with a paddock, horseback riding lessons and miles of trails. Some of Wunderlich’s trails are just for hikers.
Located between the two county parks, the Woodside Store is another site worth checking out. The store first opened in 1853 and is now a museum stocked with period items from the 1880s. The wooden structure is located at 3300 Tripp Road and is open every afternoon except Wednesdays.