A world apart, Woodside offers exclusivity and privacy as well as a strong sense of community in a rural setting. The town's culture is derived of a combination of equestrians of all disciplines (from trail riders to Olympians), eclectic artists and collectors, brilliant and innovative minds, technology titans, actors, musicians, and families with historical significance, and this translates into a down-home, warm feel. 

Within the horse community, you will find a show-barn culture as well as the Mounted Patrol of San Mateo County. These groups come together at the Woodside Trail Club, which helps maintain hundreds of miles of well-groomed riding trails across Woodside and Portola Valley. There is an annual Day of the Horse event in town, and the mounted patrol sponsors a junior rodeo as part of Woodside’s July 4 celebration.

 

Woodside offers the luxury of space. The average lot size is 1–3 acres, and home styles include older ranchers as well as exquisite estates. The area is also adjacent to several open space preserves, some of which allow biking and riding.

Furthering its country credibility, there is no downtown or shopping district in Woodside. There is a town strip with a town hall, fire station, several stores, a market, and a few restaurants. However, it is an easy trip to the conveniences of neighboring mid-Peninsula cities. Woodside does have its own public school district (K–8), and it is excellent.

• Town of Woodside website