Woodside’s great for hiking, horses, history, hanging out  

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.