Downtown Woodside, CA
Best Things To Do
This small town with big lots, nice estates and many horse trails is one of the wealthiest communities in the U.S. Rich and famous people have lived here including Joan Baez, Larry Ellison, Steve Jobs, Bill Walsh and Michelle Pfeiffer along with numerous Silicon Valley CEOs, venture capitalists, business magnates and currently about 6 billionaires.
The downtown is intentionally small but pleasant and one of the few downtowns convenient to Highway 280. See map below. You’ll enjoy a quick visit to see how the “other half” in Silicon Valley lives. You’ll find it informal but a bit expensive.
Check out these local favorites, which are good but not great, all located within a block of each other:
- Woodside Bakery & Cafe, 3052 Woodside Rd – Get a nice cookie & coffee, a pizza or meal and eat it outside on the back patio. This is a popular destination for the many bicycle riders who enjoy the wooded roads around here every weekend. website, yelp
- Buck’s of Woodside, 3062 Woodside Rd – Restaurant where many venture capital investment deals have been signed. Kids also like the atmosphere. Somewhat noisy at times. website, yelp
- Robert’s Market & Deli, 3015 Woodside Rd – Nice premium market with small town country staff who remember your name. Expensive but they carry a good variety of good food. website, yelp
- Woodside Pub, 2967 Woodside Rd – This is the town’s “special dinner” spot. It is Michelin Starred but we happen to like the burgers at the bar better than the fancy food (because we had a problem entree there once). website, yelp
- Woodside Store County Museum, 3300 Tripp Road – Not downtown but nearby. A good little old historical landmark. Free and open afternoons Tuesday, Thursday, Saturday & Sunday. website, yelp
To get a quick glimpse of residential Woodside take Mountain Home Road, adjacent Roberts Market, a couple of blocks south. Also, FYI, this town has one of the densest population of horses in the U.S. (horseback riding on local trails is big around here) and it is a popular weekend destination for bicycle riders who often end up at Woodside Bakery.
Here are some very nice nearby attractions you may want to try along with your quick visit to Woodside:
- Filoli Gardens – Beautiful gardens and mansion on Canada Road which is worth a visit if you’ve never been there.
- Madera Lounge Patio – High class indoor/outdoor lounge with a view at Rosewood Hotel off Sandhill Road/Hwy 280.
- Bicycle Sundays – A portion of Canada Road is closed to cars on Sundays for bicyclists to enjoy. It’s a nice little side trip by car too. See map.
