Located in San Mateo County, the town of Woodside is home to many technology billionaires and investment managers.
The town has 5,309 residents. Woodside’s median home price in mid-2022 is $7.35 million and the price per square foot is $1,366.
Arts & Culture Committee
Top Rated Equestrian Town in the Country
In 2020, Cowgirl Magazine named Woodside the No. 1 Equestrian Town in the country – topping well-known areas nationally like Lexington, Kentucky and Ocala, Florida! In the article, Cowgirl noted the following: “there’s an elaborate trail system that weaves throughout the whole area. Horse owners enjoy year-round riding with the balmy weather.”
The town takes great pride in being known as an Equestrian ground zero. To ensure the trails stay safe and in excellent condition, it has its own Trails Committee.
A Cycling Mecca on the Weekends
Woodside has an intentionally small business district. The town is also 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, Cañada Road, Southgate Drive, Skyline Boulevard and Highway 84. Mountain bike enthusiasts can head up 2,000 feet to Skeggs Point for near panoramic views of the Bay Area.
Santa Days and Nights at the Filoli in Woodwise
The Filoli in Woodside features really unique events for the holidays. The events include tablescapes from a number of different holiday traditions including:
- Kwanzaa
- Oshogatsu
- Yalda Night
- Lunar New Year
- Hanukkah
- Las Posadas
- Christmas
In addition, Santa flies to Filoli for Santa Days in December. For the kiddos, get their pictures with Santa on his festive golden throne. And then enjoy a warm drink and holiday treats on the Woodland Court.
For the adults, relax with friends at your own private fire pit under the magically lit oak. Imagine bringing up to 15 guests, huddled around the fire pit, drinking mulled wine and hot whiskey cider; sounds magical right?
Woodside Public Schools
Elementary and middle school-age children attend Woodside School District, one of the highest-rated districts in California. Woodside High School is part of the Sequoia Union High School District. You can verify which high school you are assigned to by clicking here.
Woodside School District
Sequoia Union High School District
Restaurant Recommendations
Hungry? We recommend you check out these restaurants:
Woodside Neighborhood Map
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