Woodside is the kind of town that feels like a deep breath: serene, spacious, and completely in tune with its natural surroundings. Tucked into the foothills of the Santa Cruz Mountains, this affluent town is known for its expansive horse properties, winding roads shaded by towering trees, and a rustic elegance that captures both Silicon Valley sophistication and old California charm.

Originally founded as a lumber town in the 1800s, Woodside became one of the earliest communities on the Peninsula to attract affluent San Franciscans seeking a rural retreat. Today, the town maintains its commitment to open space, history, and community character, with strict zoning that protects its rolling hills and equestrian setting. Though it feels like a world away, Woodside is just minutes from tech headquarters, freeway access, and the coastal beauty of the Pacific Coast Highway, making it a truly unique blend of escape and convenience.

 

• Expansive private properties surrounded by redwoods and open space
• An active equestrian community with horse trails and boarding barns
• A charming village hub with beloved restaurants and local markets
• Proximity to hiking, biking, and historic estates like Filoli Historic House & Garden
• Rich history and a rural feel just minutes from Silicon Valley
  
  
  

Life in Woodside is deeply connected to the land. Whether it’s morning rides on horseback, afternoon hikes through the redwood preserves, or a casual meet-up with friends, residents enjoy a lifestyle that’s immersed in nature and community. Weekends are spent exploring shaded trails, tending to gardens, or enjoying live music and art fairs. There’s a distinct sense of privacy and peace here, but it’s far from sleepy—Woodside is home to world-class thinkers, artists, and professionals who cherish the quiet sophistication of life off the grid but still within reach of amenities.

 

Buck’s Restaurant of Woodside is a quirky institution known for its eclectic decor and hearty American classics. With walls adorned in vintage tech artifacts and tall tales told over pancakes and omelets, it’s as much a Silicon Valley legend as it is a breakfast spot.

The Village Pub brings refinement to Woodside’s rustic core with seasonal fine dining, an award-winning wine list, and an ambiance that strikes the perfect balance between elegant and inviting. For a more casual but equally delightful stop, The Village Bakery & Cafe offers freshly baked pastries, wood-fired pizzas, delightful salads, and more served with small-town charm.

Firehouse Bistro offers a relaxed, elevated dining experience in a beautifully restored historic firehouse. With a focus on California cuisine and local ingredients, it’s perfect for a quiet evening or celebratory meal. Pioneer Saloon, a contemporary tavern, delivers craft cocktails and live tunes in a sleek yet warm setting.

The Mountain House feels like a hidden destination tucked into the redwoods, where rustic charm meets creative, seasonal menus. With its cozy wood-paneled dining room and romantic forest setting, it’s a favorite for those in search of a unique and intimate experience.

Roberts Market is a beloved local grocery staple that feels like part of the town’s fabric, offering artisanal goods, farm-fresh produce, and a deli counter that fuels many a trail lunch. Nearby, Emily Joubert Home & Garden is a beautifully curated shop filled with elegant decor, garden treasures, and one-of-a-kind gifts—blending European-inspired design with Woodside’s rustic-luxe aesthetic.

 

The Horse Park at Woodside is a premier equestrian facility that reflects the town’s deep-rooted love for horseback riding. A 501(c)(3) nonprofit, it hosts dressage, show jumping, training sessions, and cross-country events throughout the year, making it a vibrant hub for riders of all levels and equine enthusiasts alike.

Huddart Park is a serene redwood retreat offering shaded trails, scenic picnic areas, and winding paths that are perfect for hiking, trail running, or horseback riding. With miles of quiet terrain and fresh forest air, it’s a favorite escape for locals seeking a peaceful outdoor experience close to home.

Filoli Historic House & Garden is a gem just outside Woodside, known for its grand Georgian-style home, stunning terraces, and meticulously maintained gardens. Visitors can stroll through seasonal floral displays, explore the estate’s storied past, and enjoy events and exhibitions hosted throughout the year.

Spanning 167 acres, Thornewood Open Space Preserve is a hidden treasure featuring tranquil forested trails and sweeping views of the surrounding hills. Its less-traveled paths are ideal for those looking for a quiet nature walk immersed in redwoods and oaks.

Menlo Country Club offers a refined, private golf and social experience with beautifully landscaped grounds, a championship course, and upscale amenities. It’s a place where members can unwind, connect, and enjoy the elegance of the classic country club lifestyle.

Purisima Creek Redwoods Open Space Preserve offers dramatic coastal scenery in its 5,412 acres, as well as soaring redwoods and rewarding trails that range from leisurely walks to rigorous climbs. With incredible views toward Half Moon Bay and well-maintained paths, it’s a spectacular spot for a weekend hike or nature outing.

The Kings Mountain Art Fair is one of the most beloved events in the region, held every Labor Day weekend in the redwoods above Woodside. The fair features juried artists, live music, and handcrafted works in an intimate woodland setting, creating an atmosphere that’s equal parts refined and delightfully rustic.

 

• Woodside Priory
• Woodside High School
• Woodside Elementary School
• Kings Mountain Elementary School