Woodside

Welcome to Woodside

Quiet corner of Silicon Valley where equestrian community thrives located midway between San Francisco and San Jose
As one of the smaller communities in San Mateo County, Woodside is a sleepy little burg where both families with young children and retirees find a rewarding pace of life. Incorporated in the mid-1950s, Woodside has kept urbanization at bay. It has retained its rustic appeal and reputation as a refuge away from the techy glitz of Silicon Valley. With lots averaging more than one acre, Woodside is the ultimate in seclusion. It’s hard to match Woodside’s diverse and close-knit community lifestyle in its neighborhoods of Skywood/Skylonda, Family Farm/Hidden Valley, Woodside Hills, and Woodside Heights. Land along what is now Mountain Home Road once belonged to the Folger Coffee family. The area, convenient to Woodside’s town center, now consists of large estates surrounded by equestrian trails. The community, however, is not entirely isolated. Interstate 280 runs through Woodside, giving residents quick access to the best of the Bay Area.

What to Love

• Thick forest to scenic mountains to trails galore
• Easy access to the Bay Area
• Lively equestrian community

Quaint and Cozy

Among the wealthiest communities nationwide, Woodside is by no means a stuffy enclave that such a moniker would imply. Far from it.  Current residents welcome new ones with open arms. And though the pace of life here is slower, there is vibrancy to the area. With room to spare, Woodside residents are an enthusiastic group that favors outdoor pursuits, especially all things equestrian.

Dining, Shopping & Entertainment

Not exactly known for its nightlife, Woodside does enjoy a fantastic ambiance for those seeking unique dining experiences. Woodside Road, the town’s central thoroughfare, is where you’ll find well-regarded establishments, such as The Village Pub, The Firehouse Bistro, and Buck’s of Woodside, which is well-known among Silicon Valley entrepreneurs and has served as the location for many VC deals. Just down the street is Pioneer Saloon, where whiskey, open mic nights, and live music keep the locals singing well into the evening. For the more adventurous diner, at the northern end of Skyline Boulevard is The Mountain House, which serves wild game. Take Skyline south and you’ll discover the rustic, American fare of Alice’s Restaurant.

Things to Do

Although small — the entirety of the city is fewer than 12 square miles — Woodside is home to a varied geography with outdoor pursuits to match. The main draw is the thriving equestrian community. Many residents own horses, and some of the best horse trails in the state run through town. The Horse Park at Woodside is a sprawling 272-acre facility dedicated to all manner of equestrian activities, including trail riding, jumping, dressage, reining, and polo. Known for its many open spaces, the 626-acre Teague Hill Preserve and 167-acre Thornewood Preserve also offer Woodside residents and visitors amazing outdoor opportunities. For golfers, Menlo Country Club provides a challenging but picturesque course. Huddart Park is beloved by many and offers wonderful outdoor activities surrounded by redwood forests.

Schools

Due to its centralized location within the midpeninsula, Woodside sends its youth to several school districts:  Woodside elementary School District which lies in the hub of downtown Woodside offer K-8 education, Redwood City School District, Portola Valley School District, and the Sequoia Union High School District.