Known for its grand estates and sweeping landscapes, the town rests in the woodlands near the foothills of California’s northern Santa Cruz Mountains.
An equestrian, semi-rural town rich in beauty and history
The small community of Woodside is one of the oldest and most affluent in the Bay area. Known for its grand estates and sweeping landscapes, the town rests in the woodlands near the foothills of California’s northern Santa Cruz Mountains. Located just west of the peninsula’s Interstate 280, between San Francisco Bay and Pacific beaches, Woodside is 30 miles south of San Francisco and 17 miles north of Silicon Valley. Incorporated in 1956, this highly desirable enclave preserves its long heritage of vineyards, ranches, and equestrian lifestyle. You often see residents riding their horses across trails and through the streets.
The town keeps its business district small on purpose. On the main street, you will find a grocery store, bar, hardware, tack store, garden store, and a few restaurants. The intimate and reclusive character of this 12-square-mile town suits its residents, from the many high-tech financiers who live here to long-time homeowners. Some of Woodside's most high-end homes for sale and real estate can be found in the northwest areas. Tucked between Woodside Hills and Woodside Heights, you will find the lush fairways of Menlo Country Club, established in 1904.
Woodside residents value their secluded lifestyle, stately homes, and open spaces. They enjoy a comfortable pace, plenty of outdoor adventure, and easy access to the rest of the San Francisco Bay. On most days, residents jog, bike, and ride horses. Cyclists from surrounding areas pass through the town’s many routes on weekends, including King’s Mountain Road, Southgate Drive, Skyline Boulevard, and Highway 84. Locals are just a short commute from Stanford University and Silicon Valley.
The family-owned Woodside Bakery & Café offers one of the few European-style bakeries in the Bay area. They make bread and sweets from scratch daily, along with Italian-style food in their café.
The Village Pub is one of the finest restaurants in the Bay area. Rated with Michelin stars for 12 years running, the restaurant proffers an award-winning wine list of more than 3,500 labels and organic ingredients lovingly sourced from a nearby ranch. Options on their refined menu include almond wood-grilled prime filet mignon and strawberry-lemon icebox cake with strawberry-champagne jam and feuilletine.
Buck’s of Woodside is almost as famous for its colorful and odd décor as it is for being the stomping ground of Silicon Valley’s most influential dealmakers. You can tour the restaurant like a museum and enjoy the eclectic menu.
Residents of Woodside enjoy the annual May Day Parade, a time-honored tradition with a pancake breakfast, a Maypole Dance, and a Fun Run. On Independence Day, locals gather to watch the Annual Junior Rodeo. The Woodside’s Royalty equestrians herald the best bronco riders, bull riders, barrel racers, and rodeo clowns descend from the Northern California Junior Rodeo Association and surrounding towns.
On Labor Day weekend is the Kings Mountain Art Festival. It is one of the finest juried arts and crafts fairs around. Day of the Horse in the fall is celebrated as Woodside's homage to equine heritage. The event includes a Horse Fair in downtown Woodside with pony rides and demonstrations. You can go for a Progressive Trail Ride and take in original equestrian art at the art show.
People travel to Filoli, a historic house and garden on 654 acres of cultivated country estate, including a grand ballroom and nine event spaces. Events include touring the spring tulip display or summer flower show, afternoon tea, and evening jazz.
Among Woodside’s many park trails, Huddart Park and Horse Trails are some of the best known for their numerous trails, creeks, gulches, and rolling views for hiking, riding, and camping.
Woodside schools are ranked among the highest in California. Woodside School District oversees three public schools in Woodside, while the Sequoia Union High School District oversees the high school, known for its exceptional rigor and top rankings.
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