By Scott Dancer
Woodside rewards people who like quiet roads, redwood shade, and a short drive to something memorable. I have lived and worked on the Peninsula long enough to know which places my clients actually return to.
The list below covers gardens, trails, wine, dining, and live music, all within reach of town. Use it as a starting point, and confirm current hours before you head out.
Key Takeaways
- Garden outings: Filoli Historic House & Garden sits at 86 Cañada Road in Woodside and offers a 1917 house with about 16 acres of formal gardens.
- Wine on Skyline: Thomas Fogarty Winery pours tastings at 19501 Skyline Boulevard, with flights listed from $15 to $25.
- Trails and stables: Wunderlich County Park, the former Folger family ranch, is open for hiking and horseback riding.
- Live shows nearby: The Fox Theatre in Redwood City is a 1,400-seat historic venue with a Moorish interior.
Filoli Historic House & Garden
Filoli is the best-known destination in Woodside, and it is easy to see why. The estate covers about 654 acres in all, including redwoods, trails, historic orchards, and 16 acres of formal gardens around a house built in 1917.
Plan a Visit to Filoli
- Tickets and timing: Visitors choose a date and entry time online, and the site lists tickets from $35, depending on the event.
- Seasonal programs: Filoli lists Holidays at Filoli returning in November with about 350,000 lights, along with tours and wine tastings.
- Evening hours: The estate notes that hours are typically 10 AM to 10 PM during special programs, with last entry at 8 PM.
Special events can sell out, so I advise booking early. Check the official site for the schedule that applies to your visit.
Thomas Fogarty Winery on Skyline
Up on Skyline Boulevard, Thomas Fogarty Winery offers a wine stop in the hills above town. The winery says it has grown Chardonnay and Pinot Noir for four decades.
Details for Your Tasting Visit
- Room hours: The listed hours are noon to 5 PM Monday through Friday and 11 AM to 5 PM on weekends.
- Flights and fees: Flights of five wines are listed at $15, $20, or $25, and one tasting fee is waived for each $100 of wine purchased.
- Guided tours: Tours for guests 21 and older are listed at $45 or $75 per person and include uphill and downhill walking.
The winery warns that cell service on Skyline is poor, so I suggest saving directions before you leave town. Advance tour bookings keep the day simple.
Wunderlich Park and Folger Stable
Wunderlich County Park at 4040 Woodside Road mixes redwood forest, open meadows, oaks, and madrones. San Mateo County Parks notes that the land was once the Folger family ranch and that the estate stable has been restored as a historic site.
What Visitors Can Do
- Trail hiking: The park’s trails are open for hikers who want shaded climbs and meadow views.
- Horseback riding: The same trails are open to riders, which fits the equestrian character Woodside is known for.
- Picnics: Tables are available on a drop-in basis only, and nothing can be reserved in advance.
Park advisories can change, so I recommend a quick look at the county page before you go. Pack water and plan your route in advance.
Buck’s and The Village Pub for Dinner
Woodside’s dining scene ranges from playful to polished. Two restaurants on Woodside Road show that range well.
Two Very Different Tables
- Buck’s of Woodside: Located at 3062 Woodside Road, this restaurant opened in 1991 and describes itself as half restaurant and half museum, with folk art, model planes, and vintage memorabilia.
- The Village Pub: Found at 2967 Woodside Road, it holds one Michelin Star in the 2026 guide for American contemporary cuisine.
- Reservations: Buck’s accepts online reservations and walk-ins, while a fine-dining table at The Village Pub is wise to arrange ahead.
Both places draw locals as well as visitors. Confirm hours directly, since they vary by day.
Live Music and Art Beyond Town
A short drive can take you to historic theaters and museums. Two favorites sit in Redwood City and on the Stanford campus.
Stage and Gallery Options
- Fox Theatre: The 1,400-seat venue at 2215 Broadway in Redwood City opened in 1929 and has hosted Etta James, Tony Bennett, and B.B. King.
- Cantor Arts Center: Admission to the museum at 328 Lomita Drive is listed as free, with no reservation required.
- Gallery notes: The museum lists some galleries as closed for reinstallation, and Thursday hours run until 8 PM.
Check the theater calendar for current shows before you make plans. Museum hours differ by day, so confirm them as well.
FAQs
How far are the best entertainment spots near Woodside?
Filoli, Thomas Fogarty Winery, Wunderlich Park, and the dining rooms on Woodside Road are all in or just outside town. Redwood City and Stanford are a short drive away, though travel time depends on traffic and the route you choose. I suggest mapping your plan the day before.
Which of these places work for a quiet weekend?
Wunderlich Park and Filoli suit a slower pace, with trails and gardens to explore. The winery and a meal at Buck’s make easy additions to the same day. Hours change, so confirm before you leave.
Do these attractions matter to someone moving to Woodside?
Many of my clients choose the area for its access to open space and local dining. A weekend at a few of these places can help you decide whether the rhythm of town suits you. I am glad to share my own favorites during a showing.
Contact Scott Dancer Today
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Scott Dancer today to find a Woodside home that puts these favorite places close to your daily routine.
