It doesn’t take spending much time in Woodside before you start to realize that horses play a pertinent part in this community as it has for all of Woodside’s history. As you drive through town, you will see many horse properties and people out riding their horses. And if you get out of your car and hit the trails, you may see horses on the trails too. Woodside boasts an extensive trail system for horses and humans alike. The population of Woodside is small at about 5,500 and the town is about 12 square miles. The community has one elementary school that runs from K-8. Woodside High School is the high school that serves this area. Woodside is one of the more expensive communities on the peninsula and has many large estates. There is a quaint and popular shopping district at the intersection of Woodside & Canada roads that is a focal point for Woodside and provides a special place to shop, eat, drink, and take in the vibe of the town.