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The Top Attractions in Woodside, CA, For Locals or Tourists

06/10/24  |  Stephanie Nash

Exploring the best of Woodside's local gems.


Nestled amidst the verdant hills of Silicon Valley, Woodside, California, emerges as a bastion of elegance and exclusivity. Renowned as one of the wealthiest neighborhoods in the nation, Woodside embodies the epitome of country living, where sprawling horse ranches and modern mansions coexist harmoniously. With its Western-inspired downtown exuding quaint charm, Woodside stands as a testament to the seamless fusion of sophistication and simplicity.

Amidst the splendor of Woodside's countryside, a plethora of attractions await discovery. From historic landmarks to scenic parks and world-renowned wineries, there's no shortage of experiences to enchant and delight those who venture into this idyllic enclave. Whether you're seeking outdoor adventure, cultural enrichment, or simply a leisurely day out, Woodside offers an array of attractions that cater to every taste and preference.

Menlo Country Club


For golf enthusiasts, the Menlo Country Club stands as a premier destination. Nestled amidst 140 acres of pristine woodlands, this exclusive private club boasts an 18-hole championship course designed by legendary architect Alister MacKenzie. With its challenging layout and stunning scenery, the Menlo Country Club offers an unparalleled golfing experience for players of all skill levels.

Filoli Historic House & Garden


Step back in time with a visit to the Filoli Historic House & Garden. This historic estate, dating back to the early 20th century, boasts 16 acres of beautifully landscaped gardens, as well as a meticulously preserved Georgian-style mansion. Visitors can explore the estate's stunning grounds, marvel at its architectural splendor, and learn about the history of the families who once called Filoli home.

Wunderlich County Park


Nature enthusiasts will delight in a visit to Wunderlich County Park. This sprawling park encompasses over 1,000 acres of pristine wilderness, including dense forests, meandering creeks, and scenic hiking trails. Whether you're picnicking beneath the towering redwoods, horseback riding along the equestrian trails, or simply taking a leisurely stroll through the woods, Wunderlich County Park offers a peaceful retreat from the hustle and bustle of city life.

Thomas Fogarty Winery


Wine lovers won't want to miss a visit to the Thomas Fogarty Winery. Perched atop the Santa Cruz Mountains, this award-winning winery offers breathtaking views of the surrounding vineyards and the San Francisco Bay beyond. Visitors can sample a variety of handcrafted wines, take a tour of the estate's state-of-the-art winemaking facilities, and enjoy a leisurely picnic on the winery's expansive grounds.

Canyon Ranch


For those seeking relaxation and rejuvenation, Canyon Ranch offers the perfect escape. This luxurious wellness retreat, nestled amidst the scenic beauty of Woodside's hillsides, offers a range of holistic treatments and activities designed to promote health and well-being. From yoga and meditation classes to spa treatments and gourmet dining, Canyon Ranch provides a tranquil oasis where guests can unwind and recharge.

Exploring Woodside's Local Attractions


For equestrian enthusiasts, The Horse Park at Woodside stands as a mecca for all things equine. This premier equestrian facility hosts a variety of events and competitions throughout the year, including dressage, show jumping, and eventing. With its state-of-the-art facilities and scenic surroundings, The Horse Park at Woodside offers a unique opportunity to experience the beauty and grace of horseback riding amidst the natural splendor of Woodside's countryside.

Thornewood Preserve


Nature lovers will find solace amidst the tranquility of Thornewood Preserve. Spanning over 654 acres of pristine wilderness, this protected area offers a network of hiking trails that wind through dense forests, meadows, and creeks. Visitors can immerse themselves in the sights and sounds of nature, encountering an array of native flora and fauna along the way. Whether you're birdwatching, picnicking, or simply enjoying a peaceful stroll, Thornewood Preserve provides a welcome escape from the hustle and bustle of everyday life.

Woodside Store Park


Step back in time with a visit to Woodside Store Park, a historic landmark that offers a glimpse into Woodside's storied past. This beautifully preserved general store, dating back to the 1850s, provides insight into the area's early days as a logging and farming community. Visitors can explore the restored store, browse exhibits detailing Woodside's rich history, and enjoy a leisurely picnic on the grounds. With its rustic charm and picturesque surroundings, Woodside Store Park offers a delightful retreat for history enthusiasts and nature lovers alike.

Exploring Woodside's Local Attractions


Whether you're a local resident looking to explore your own backyard or a visitor eager to discover the charms of Woodside, there's no shortage of attractions to explore in this idyllic community. From historic landmarks and scenic parks to world-class wineries and luxurious wellness retreats, Woodside offers something for everyone to enjoy.

Discover Woodside's Charm with Stephanie Nash


Ready to experience the charm and elegance of Woodside, CA, firsthand? Stephanie Nash is your trusted guide to exploring all that this idyllic enclave has to offer, boasting over 30 years in the industry. With her unparalleled expertise in Woodside real estate and deep understanding of the local market, Stephanie is uniquely positioned to help you find the perfect home to suit your lifestyle and preferences.

Whether you're searching for a sprawling estate nestled amidst the rolling hills, a quaint cottage in the heart of downtown, or a luxurious retreat with panoramic views of the surrounding countryside, Stephanie can make your dreams a reality. Contact her today to schedule a consultation and begin the search for your dream home in one of Silicon Valley's most coveted neighborhoods.

*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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