Woodside

One of the country’s wealthiest communities, this picturesque small town is also home to many open-space preserves and equestrians.

Welcome to Woodside

One of the country’s wealthiest communities, this picturesque small town is also home to many open-space preserves and equestrians.
 
Woodside is a small incorporated town in San Mateo County that is most renowned for being among the wealthiest communities in the entire country and the home of several billionaires. The area is predominantly residential, with plenty of open space reserves and nature trails. 
 
Given the amount of lush, open land here, Woodside has evolved into a notable horse country, and many residents participate in equestrian activities or maintain farmland. The local government maintains a network of trails specifically for horses. The small business district only includes shops and restaurants, including a Michelin-starred restaurant and the infamous Buck's of Woodside, a restaurant where many investment deals have been signed.


What to Love

  • Lots of spacious homes 
  • Horse properties
  • Buck’s of Woodside
  • Scenic and woodsy
  • Small-town vibe
  • Great for bicyclists 

 

People & Lifestyle

With only about 5,000 residents, Woodside is a distinctly rural town with a different culture that sets it apart from Silicon Valley. It's far more idyllic and less tech-focused than the surrounding Silicon Valley cities. Even the business district is tiny, with only a handful of eateries and stores.

Woodside does have its own post office and supermarket, but you'll likely need to drive to one of the other cities for any significant shopping trips. 
 
That being said, the people who are attracted to Woodside — empty-nesters, families, retirees, and the like — come here specifically for the peaceful vibe and woodsy feel. Nature lovers adore the great hiking, mountain biking, and natural beauty found in the rustic town.


Dining, Entertainment & Shopping 

Rosetti's Alpine Inn is one of the oldest continually open taverns in California. This rustic roadside spot continues to attract customers to its beer garden for its delicious burgers and beers.
 
Festooned with knickknacks and whimsy, Buck's of Woodside has become a Silicon Valley fixture and a comfort food staple for visitors and locals alike. Over the years, Buck's has become a popular meeting ground for tech entrepreneurs and venture capitalists seeking a cozy place to meet up and exchange ideas. The original owner, James McNiven, recently retired from running Buck's, but his sons have stepped in to run the restaurant and continue his legacy. 
 
A cozy, eco-friendly hotspot, Alice's Restaurant sees a melting pot of individuals — from motorcyclists to musicians — stop by to enjoy a fantastic meal. Patrons continually return to Alice's for their homemade pie, sweet potato fries, and famous scrambles.
 
The Village Bakery in Woodside is a full-service bakery and cafe serving everything from cookies, pies, cakes, and pastries to gluten-free treats to wedding cakes! This spot has the honor of being one of the last remaining European bakeries in the Bay Area.


Things to Do

The Pioneer Saloon has been a Woodside staple for years. On the weekends, residents love visiting this no-frills watering hole for live music, beer and karaoke. 
 
Established in 2015, the Chaparral Ranch in Wunderlich County Park is a gorgeous ranch surrounded by open space preserves, nature trails, and stunning Bay views. People come from all over the Bay Area to experience the rich equestrian community cultivated by the Chaparral Ranch owners. Whether you're looking for lessons, adventure rides, or just coming for the atmosphere, Chaparral Ranch is a unique experience for all outdoor lovers.
 
The Thomas Fogarty Winery has been producing mostly Estate-grown wines since 1981, with the specific goal of cultivating top-tier Chardonnay and Pinot Noir from the soils of the neighboring Santa Cruz Mountains. The winery's tasting room is geared toward wine enthusiasts, but they love teaching newcomers about wine and let them participate in their Signature Tasting to try their single-vineyard wines.
 
Situated on King Mountain's western slope in Woodside, the Purisima Creek Redwoods Open Space Preserve is notable for its coastal redwoods, coastal scrub, hardwood forests, madrones, and Douglas firs. The preserve was originally established with a $2 million gift from the Save the Redwoods League. Overlooking Half Moon Bay, the preserve boasts more than 20 miles of trails for horseback riding, hiking, and biking, although dogs are not allowed.


Schools 

Public elementary and middle schools in Woodside are operated by the Woodside Elementary School District, while the Sequoia Union High School District operates Woodside High School.

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