By Scott Dancer
People who settle in Woodside tend to stay for life, and it is easy to see why. This is a rare place where you can keep horses, walk among redwoods, and still reach Silicon Valley in minutes. After selling homes here since 1984, I still love showing people what makes Woodside so special. Here is a look at the town I am proud to call home, and the things that keep people here for generations.
Key Takeaways
- Woodside offers rural, private living minutes from Silicon Valley.
- The town's equestrian tradition shapes its trails and character.
- Redwood parks and open space are part of everyday life here.
- A small, historic town center gives Woodside its personality.
A Rare Kind of Country Living
Woodside sits in the hills above the Peninsula, a town of large estates, winding lanes, and wooded privacy. Strict zoning and a long commitment to open space have kept it rural even as the surrounding valley grew. That is a big part of why people fall in love with it. Drive a few minutes off the main road and the pace slows, the traffic disappears, and the trees close in around you.
Here you can own acres of land, plant a garden or an orchard, and still be a short drive from Palo Alto and Menlo Park. Few places offer that mix of seclusion and access. You can spend the morning on a trail and still make an afternoon meeting in the valley. That balance is the heart of the Woodside appeal.
What Country Living Looks Like Here
- Large parcels with room for gardens, orchards, or pastures
- Quiet, tree-lined roads and true privacy
- Easy access to Silicon Valley for work and travel
- A landscape of hills, oaks, and towering redwoods
An Equestrian Town at Heart
Woodside is one of the last true horse towns on the Peninsula. Many properties include stables or riding rings, and the town maintains a network of trails that connect neighborhoods and open spaces. You will often see riders on the shoulder of a country road, and drivers here are used to sharing the way.
This equestrian tradition is more than a hobby, it is part of the town's identity. It shapes how the land is used and why so many residents value open space. The town's riders, from young students to lifelong horse owners, are a familiar part of daily life. Even neighbors without horses tend to treasure the pastoral feel it creates.
Signs of Woodside's Horse Country
- Private stables, paddocks, and riding rings on many estates
- A town-maintained network of riding and walking trails
- Riders sharing the quiet roads throughout the week
- Wunderlich County Park, with miles of equestrian trails
Parks and Redwoods at Your Doorstep
Few towns put this much natural beauty within reach. Huddart Park spreads across more than 900 acres of redwood forest, meadows, and creeks, with trails for hiking and family outings. Nearby Wunderlich County Park offers redwood groves and grassy hillsides laced with trails.
For bigger adventures, Purisima Creek Redwoods and Windy Hill Open Space Preserve sit just up the ridge. Weekend mornings here often start with a walk under the trees. The redwoods give the whole town a cool, quiet character you feel the moment you arrive. For many residents, this daily access to nature is the best part of living here.
Green Spaces Locals Love
- Huddart Park, with redwoods, meadows, and family trails
- Wunderlich County Park, popular with hikers and riders
- Purisima Creek Redwoods along the Skyline ridge
- Windy Hill Open Space Preserve, with wide Peninsula views
History and a Town Center With Character
Woodside wears its history well. The historic Woodside Store, dating to the 1850s, still stands as a reminder of the town's early logging days. Just up the road, the grand estate and gardens at Filoli draw visitors from across the region who come for the historic house and seasonal blooms.
The small town center along Woodside Road has real personality. Buck's of Woodside, a beloved local diner known as a Silicon Valley meeting spot, sits near Roberts Market and the old Pioneer Saloon. These are the kinds of gathering places where neighbors run into each other and deals have quietly been made for decades. It is a small center, but it gives the town a real sense of community.
Local Landmarks Worth Knowing
- The historic Woodside Store from the town's logging era
- Filoli's mansion and formal gardens nearby
- Buck's of Woodside, a legendary local gathering place
- Roberts Market and the Pioneer Saloon in the town center
Frequently Asked Questions
What is Woodside known for?
Woodside is known for its rural, equestrian character, its redwood parks, and its large private estates just minutes from Silicon Valley. That rare mix is a big part of what makes Woodside so special.
Can you keep horses in Woodside?
Yes, Woodside is one of the Peninsula's premier horse communities, with many properties zoned for stables and riding. The town also maintains an extensive network of trails.
Is Woodside close to Silicon Valley?
Very. Woodside sits just above Palo Alto and Menlo Park, so residents enjoy country living with a short drive to work, dining, and the airport corridor.
Reach Out to Scott Dancer Today
If Woodside sounds like the life you have been picturing, I would love to help you find your place here. I know these hills, roads, and neighborhoods better than anyone, and I have helped families call Woodside home for four decades. Whether you want acreage for horses or a quiet retreat under the redwoods, I can help you find it.
When you are ready to explore living here, reach out to me,
Scott Dancer. I would be glad to show you around the town I know and love so well, and to help you find a property that fits the life you want.
