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True to its name, Woodside is an idyllic small town nestled in the redwoods of San Mateo County. Stay with Inspirato at Canyon Ranch Woodside, a wellness haven offering daily activities like yoga, outdoor fitness challenges, meditative forest walks, and much more.
Woodside is the perfect place to get away from it all and immerse yourself in nature. This small town of about 5,000 residents, incorporated into San Mateo County, offers a distinctly rural feel, much different from its Silicon Valley neighbors. Many of the elites in the tech and business world have chosen to make this their home, though—which is why Woodside is one of the wealthiest communities in the country. And it’s easy to see why: The natural beauty of the area is something to behold. Enjoy myriad trails for hiking, mountain biking, and horseback riding that take you through breathtaking redwood forests. Quaint and quiet downtown Woodside has only a handful of eateries, but they are worth a visit—one is even Michelin-starred. And no visit would be complete without a peek inside the Woodside Store, a California Historical Landmark.
This fully restored wooden structure was once used as a general store, post office, and dentist’s office in the heyday of Woodside’s logging industry. Today, this free museum features artifacts dating back to the 1800s.
This winery and vineyard offers a wide selection of organic and sustainable California-grown wines. Visit for a tour, outdoor tasting—or both—in a beautiful Santa Cruz mountain setting.
Step back in time at this 654-acre historic estate featuring a stunning home, manicured gardens, and nature trails. Visit the on-site cafe for a glass of wine or afternoon tea, seasonal activities, tours, art shows, and more.
Woodside enjoys a mild Mediterranean climate with cool, wet winters and warm, dry summers. With an average of 261 days of sunshine and moderate temperatures that rarely feel too hot or too cold, it’s easy to spend time outdoors year round.