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Things to Do in Woodside, CA

07/29/24  |  Stephanie Nash

Discover the best activities and hidden gems that make Woodside a must-visit destination for both locals and tourists alike.


Nestled in the heart of Silicon Valley, Woodside is a serene and picturesque town that offers a blend of natural beauty, historical charm, and luxurious amenities. Whether you're a long-time resident or a visitor looking to explore, Woodside has a wealth of activities to keep you engaged and entertained. From historic estates and scenic parks to world-class wineries and wellness retreats, there’s no shortage of things to do in Woodside, CA.

Explore the Filoli Historic House & Gardens


One of Woodside's crown jewels is the Filoli Historic House & Gardens, a breathtaking estate that offers a glimpse into the region's rich history and stunning natural beauty. Built in the early 20th century, Filoli is a magnificent example of the Georgian Revival style, set against the backdrop of the Santa Cruz Mountains.

Visitors to Filoli can explore the opulent mansion, which features beautifully preserved interiors and a fascinating collection of art and antiques. Guided tours provide insights into the history of the estate and its former residents, offering a captivating journey through time.

The real highlight of Filoli, however, is its extensive gardens. Spanning 16 acres, the gardens are meticulously maintained and feature a stunning array of flowers, plants, and trees. From the formal rose garden to the serene woodland paths, there’s something to delight every nature lover. Seasonal events and horticultural workshops further enhance the experience, making Filoli a must-visit destination in Woodside.

Enjoy a Wellness Staycation at Canyon Ranch


For those seeking relaxation and rejuvenation, a wellness staycation at Canyon Ranch in Woodside is the perfect escape. This luxurious wellness retreat offers a holistic approach to health and well-being, combining world-class amenities with the tranquility of its natural surroundings.

Guests at Canyon Ranch can indulge in a variety of wellness activities, including yoga, meditation, fitness classes, and spa treatments. The retreat's expert staff is on hand to provide personalized wellness plans and guidance, ensuring a transformative experience.

In addition to its wellness programs, Canyon Ranch offers exquisite accommodations and gourmet dining options emphasizing nutritious and delicious cuisine. The serene environment, surrounded by towering redwoods and lush gardens, provides the perfect setting for relaxation and reflection. Whether you're looking for a weekend getaway or a longer retreat, Canyon Ranch offers an unparalleled wellness experience in the heart of Woodside.

Delight in a Tasting at Thomas Fogarty Winery


No visit to Woodside would be complete without experiencing the region's renowned wine culture. Thomas Fogarty Winery offers an exceptional tasting experience that combines stunning views, award-winning wines, and a warm, welcoming atmosphere.

Perched on the slopes of the Santa Cruz Mountains, Thomas Fogarty Winery boasts panoramic views of the vineyards and the valley below. The winery's tasting room is an inviting space where visitors can sample a variety of wines, including Chardonnay, Pinot Noir, and Cabernet Sauvignon. Each wine reflects the region's unique terrain and the winery's commitment to sustainable farming practices.

In addition to tastings, Thomas Fogarty Winery offers guided tours of the vineyards and winery, providing insights into the winemaking process and the history of the estate. Special events, such as wine and food pairings and seasonal celebrations, further enhance the visitor experience. Whether you're a wine connoisseur or a casual enthusiast, a visit to Thomas Fogarty Winery is a delightful way to spend an afternoon in Woodside.

Connect with Nature at Huddart Park or Thornewood Open Space Preserve


Woodside's natural beauty is one of its greatest assets, and there are plenty of opportunities to connect with nature through its numerous parks and open spaces. Two of the most popular destinations for outdoor enthusiasts are Huddart Park and Thornewood Open Space Preserve.

Huddart Park is a sprawling 973-acre park that offers a variety of recreational activities for visitors of all ages. The park features an extensive network of hiking trails that wind through towering redwoods, lush fern groves, and open meadows. Popular trails include the Crystal Springs Trail, which offers stunning views of the surrounding mountains, and the Redwood Trail, a family-friendly path that showcases the park's majestic redwood trees. In addition to hiking, Huddart Park offers picnic areas, playgrounds, and equestrian trails, making it a great destination for a day out with family and friends. The park's peaceful setting and abundant wildlife provide a refreshing escape from the hustle and bustle of everyday life.

For a more tranquil and secluded experience, Thornewood Open Space Preserve is a hidden gem that offers pristine natural beauty and quiet solitude. This 167-acre preserve features a diverse landscape of forests, grasslands, and wetlands, providing a haven for a variety of plant and animal species.

The preserve's main trail, the Schilling Lake Trail, is a moderate hike that takes visitors through dense woodlands and open fields, eventually leading to the picturesque Schilling Lake. The trail is well-maintained and offers plenty of opportunities for birdwatching and photography. The serene environment and scenic vistas make Thornewood Open Space Preserve a perfect destination for those looking to connect with nature and enjoy a peaceful retreat.

Tee Off at Menlo Country Club’s Course


Golf enthusiasts visiting Woodside will find a premier golfing experience at the Menlo Country Club. This prestigious private club boasts an 18-hole championship golf course renowned for its challenging layout, impeccable maintenance, and stunning views.

The Menlo Country Club’s course is designed to offer a rewarding experience for golfers of all skill levels. The course features rolling fairways, strategically placed bunkers, and fast greens, providing a test of skill and strategy. The course's scenic beauty, with its mature trees and sweeping vistas, adds to the enjoyment of the game.

In addition to the golf course, Menlo Country Club offers top-notch facilities, including a driving range, practice greens, and a well-appointed clubhouse. Members can enjoy a variety of amenities, including dining, social events, and fitness facilities. While the course is private and requires membership, those who have the opportunity to play at Menlo Country Club will find it to be one of the finest golfing experiences in the area.

Discover Your Dream Home in Woodside


Are you enchanted by the unique charm and attractions of Woodside, CA, and considering making this picturesque town your home? Whether you're exploring the historic Filoli estate, savoring fine wines at Thomas Fogarty Winery, or hiking through the lush landscapes of Huddart Park, there are countless things to do in Woodside, CA. This delightful town offers a unique blend of natural beauty, cultural heritage, and modern luxury, making it an ideal destination for visitors and a wonderful place to plant roots.

Reach out to Stephanie Nash to find the perfect property that meets your needs. As a real estate expert since 1991, Stephanie has the experience and know-how to help you explore Woodside real estate and snag your ideal property. Contact Stephanie Nash today to get started!

*Header image courtesy of Unsplash



Stephanie Nash

Stephanie Nash

About The Author

For more than three decades, Stephanie Nash has been one of the Peninsula’s most trusted and proven real estate advisors, serving Woodside, Portola Valley, Atherton, Redwood City, Emerald Hills, San Carlos, Half Moon Bay, and the surrounding communities from Burlingame to Los Gatos.

Born and raised on the Peninsula, Stephanie brings true insider knowledge of the region; its micro-neighborhoods, school corridors, country-property enclaves, and the lifestyle features that make this area so coveted: sunny weather, an easygoing spirit, hiking trails, large-parcel retreats, ocean-view hillsides, and world-class food and culture.

A career built on experience, ethics, and results

Stephanie began her real estate career in 1987 working in local title companies before becoming the assistant to a top-producing agent. She earned her real estate license in 1991, and since then has built a reputation as a solutions-driven, ethical, and steady negotiator who guides clients through every complexity of a California transaction.

Her track record includes everything from luxury estates to rural acreage to trust and estate sales, including the successful sale of a 500-acre property, a transaction requiring extensive due diligence, jurisdictional navigation, and long-term strategy.

Nationally recognized performance

Stephanie has been recognized multiple times by RealTrends as one of the “Best Agents in America,” most recently in 2024; an honor reserved for the top tier of agents nationwide based on verified production.

Expert Witness in Real Estate Matters

In addition to client representation, Stephanie now serves as a retained Expert Witness in California real estate cases—including valuation disputes, fiduciary sales, marketing standards, agent performance, disclosure practices, and industry-standard care.

What clients rely on her for

Whether you are buying, selling, downsizing, expanding, or handling a trust/estate sale, Stephanie offers:

  • Deep regional expertise across multiple Peninsula micro-markets

  • Strong negotiation skills grounded in fairness, strategy, and consistent communication

  • Experience in complex transactions (trusts, estates, multiple-heir negotiations, title defects, rural land issues)

  • Compassionate guidance rooted in decades of hands-on client service

  • Unmatched availability and responsiveness

Clients praise her listening skills, honesty, and ability to navigate even the most emotional or complicated sale with clarity and professionalism.

A life built around community and care

Stephanie is deeply grateful for her family, her life on the Peninsula, and the meaningful relationships formed through her work. 

Work With Stephanie

Stephanie respects residential real estate’s dual role as a personal investment and chief financial one. Whether you are buying or selling a home, it will likely be one of the largest financial decisions you make. Stephanie will be with you every step of the way to expertly guide you.

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