Woodside is a small town in beautiful San Mateo County, located at the base of the Foothills in San Mateo County, on the beautiful San Francisco Peninsula. It has a smaller population, around 5300 per the 2010 census. Woodside is home to many of the Silicon Valley elite and is among the wealthiest communities in the entire country. Large estates and multi-acre lots are the norm, and there is very small downtown consisting of a few restaurants, a high end local market as well as some specialty shops. Horses and trails weave their way through town, and there are many hiking trails as well. Woodside is where you want to live if you desire privacy, beauty and a small town feel and excellent public schooling from K-8.