Woodside is located on the San Francisco Peninsula, midway between San Jose and San Francisco, just north of Silicon Valley, in San Mateo County. The infamous San Andreas fault runs through town.

Much of Woodside is wooded, with redwoods dominating in the western hills and more oaks and eucalyptus in the lower areas. San Francisco Bay lies to the east, while Pacific Ocean beaches lie to the west. The Santa Cruz mountains separate Woodside from the ocean and extend down to Monterey Bay about forty miles south.

The intentionally small business district includes a few restaurants (Buck’s, Woodside Bakery & Cafe, and The Village Pub), a grocery store (Roberts Market), a saloon (the historic Pioneer Saloon), a hardware and horse tack store (Roberts Hardware and Tack), an art gallery and picture framing store (Woodside Gallery), a home and garden store (Emily Joubert), realtors (Carey Realty, Coldwell Banker, Alain Pinel, Remax), a few venture capital funds (including Crosspoint Ventures, Tenaya Capital, and The Photonics Fund), a cleaner, a post office, and an educational consulting and tutoring company (Cardinal Education). Outside of the business district are the Stillheart Institute educational event center, Skywood Trading Post, the Mountain Terrace event center, and the following restaurants: Bella Vista, The Little Store, The Mountain House and Alice’s. The Village Pub recently was awarded a high honor for restaurants: a Michelin star. The town is home to the famous Buck’s of Woodside restaurant, which is well known among Silicon Valley entrepreneurs as the location where many VC investment deals have been signed. The inside of the restaurant is decorated with historic Silicon Valley artifacts. The corporate headquarters for Fisher Investments sits atop Kings Mountain in Woodside.

Horses are part of the local culture. Numerous residents keep horses, and the town government maintains a network of horse trails.Some resident’s homes are even considered farms. The town is also quite popular among local cyclists and draws them in large numbers on weekends. The most popular road cycling routes include Old La Honda Road, King’s Mountain Road, CaƱada Road, Southgate Drive, Skyline Boulevard and Highway 84. The Tour of California bicycle race includes several roads along and adjacent to CA-84 and Skyline Boulevard.

Woodside is home to a number of open space preserves, including the Purisima Open Space (which is part of the Midpeninsula Regional Open Space), where both horseback riding and bicycling is allowed. For mountain biking, the famous Skeggs Point is located in Woodside along Skyline Boulevard. There is also an extensive archery course maintained by volunteers in the adjacent Huddart County Park.