Beautiful area dotted with wooded hills and extensive trail systems neighbors the small, sophisticated town of Woodside.
Portola Valley is considered one of the most beautiful towns in San Mateo County, and it's easy to see why when you look at the lush green spaces, extensive trail system, redwood forests, and wooded hills. This quiet area has mastered the art of seamlessly blending the pastoral eloquence it is revered for with modernity.
Portola Valley neighbors Woodside, an idyllic woodsy town culturally different from the high-tech Silicon Valley. Woodside is much smaller and a known haven for nature lovers due to the abundant natural beauty and plethora of hiking and biking areas. Surprisingly, even though both towns pride themselves on being a picturesque respite away from the larger cities, they are two of the wealthiest neighborhoods in the nation.
What to Love
Lush wooded areas and trails
Excellent public school system
Valued historical heritage
Rural suburban neighborhoods
Spacious and large lot sizes
Hundreds of acres of open space
People & Lifestyle
Woodside and Portola Valley attract similar demographics, primarily families, nature lovers, retirees, and empty-nesters looking for a small town where they can escape. Both towns are affluent, with expensive ranch homes tucked behind sprawling redwood trees and sweeping large lots for custom builds. Portola Valley is a little less costly but still on the higher end. It doesn't get much better than this if you appreciate the countryside and want to live in a woodsy small town. The price of privacy, seclusion, and tranquility is too alluring to ignore for many.
Dining, Entertainment & Shopping
Portola Valley and Woodside are home to numerous acclaimed restaurants and cozy cafés. Are you a fan of the old-school "classic diner" vibe? Nestled in a redwood grove, Alice's Restaurant is perfect for anyone who wants to chow down on a mouth-watering burger or sample delicious BBQ. Rossotti’s Alpine Inn and beer garden is a traditional eatery and one of California's second-oldest continually operating taverns. This 167-year-old rustic roadside spot serves hearty burgers and great beer on the banks of Los Trancos Creek.
Seafood lovers love the East Coast-style dishes served at Old Port Lobster Shack. The cuisine perfectly complements the laid-back wharfside atmosphere.
Located among the scenic redwoods of Portola Valley, Parkside Grille grounds itself in a menu full of comfort food with bold flavors and innovative twists on classics. Portola Kitchen combines the best of Italian cooking with Californian cuisine. Enjoy homemade pasta and thin-crust pizza prepared in a charming rustic space perfect for casual meals with friends or special occasion dinners.
Renowned for its high-end ambiance and extensive brunch, lunch, and dinner menus rooted in its Mediterranean and French influences, The Village Pub in Woodside has become a locally and nationally recognized fine dining destination. The Village Bakery is a Woodside staple open daily for indoor and outdoor dining, takeout, and delivery.
Buck's of Woodside is famous for its abundance of knickknacks. Various whimsical decorations ornament the interior of this Silicon Valley fixture. You can rely on Buck's to provide a good time and great food.
Things to Do
The Filoli Historic House and Garden is a country house set on 16 acres of formal gardens on a sprawling estate in Woodside. You might recognize it from television shows like Dynasty and various Hollywood films. Not only can you explore the extravagant gardens, but the house and the estate itself are also open to visitors itching to explore.
Wine connoisseurs will enjoy visiting the Thomas Fogarty Winery and Vineyards. Offering a wide selection of California-grown wines, Thomas Fogarty Winery prides itself on using sustainable farming practices. Whether you want to learn about the winemaking process or reserve a wine tasting, the vineyards are a beautiful and idyllic place to visit alone or with a group.
Windy Hill Open Space Preserve is a notable regional park because it contains the only stretch of land throughout the peninsula range that isn't forested. The name of this breezy, 1,414-acre preserve comes from its open grassland ridges and distinctive grass-covered hilltop.
Schools
The Portola Valley Elementary School District has two public primary schools, including Corte Madera School (4-8) and Ormondale School (K-3). The public high school is Woodside High School. Portola Valley is also home to two noted private schools in Woodside Priory School (6-12) and Woodland School (PK-8).