A late-August Saturday in Woodside has a shape most residents settle into without thinking. It starts in cool shade at 500 feet of elevation, climbs through redwood switchbacks to a sunlit ridge, and ends at a village grocery counter that has been in the same spot since the 1880s. The town's geography does the work of an itinerary.
What follows is not a list of things to do. It is a single argument: Woodside's two elevations, canyon floor and Skyline crest, are best treated as one continuous weekend, and the calendar this month rewards that thinking.
The 2,000-foot day
The trail network above town lets you cover both elevations on foot in a morning. The section of Skyline Trail between Huddart and Wunderlich is six miles of rolling singletrack through redwood forest, and it links the two lower entrances into a loop that peaks near Skyline Boulevard. The Skyline Trail runs gently graded through redwood and Douglas-fir just below the crest of the Santa Cruz Mountains, follows one of the few remaining segments of the old California Riding and Hiking Trail established in 1954, and stays shaded enough to serve as a summer retreat from valley heat.
Once you are on the ridge, you are within a short drive of Thomas Fogarty Winery, perched 2,000 feet above Silicon Valley at 19501 Skyline Boulevard. The winery was founded in 1981 by Dr. Thomas Fogarty, a Stanford cardiovascular surgeon and inventor, and now produces single-vineyard Pinot Noirs, Chardonnays, Merlots and Cabernets from the Santa Cruz Mountains. The point is not the tasting itself. It is that residents can hike from 500 feet of shaded creek bottom to a ridge tasting room in the same outing, without leaving the 94062 ZIP code.
Two parks, one weekend
Huddart and Wunderlich read as siblings on a map, and locals talk about them interchangeably, but they answer different questions.
| Huddart | Wunderlich | |
|---|---|---|
| Address | 1100 Kings Mountain Rd | 4040 Woodside Rd |
| Acres | 973 | 942 |
| Miles of trails | 24 | 17 |
| Parking | $6 | Free |
| Bikes | Designated trails only | Not permitted |
| Pets | Not permitted | Not permitted |
The numbers come from Huddart's 973 acres, 24 miles of trails, $6 parking, and cycling on designated trails only and Wunderlich's 942 acres, 17 miles of trails, free parking, and prohibition on pets, cyclists and smoking.
The park histories explain the trail character. Under J.A. Folger's ownership, the Wunderlich land became a recreation area, and wagon trails and old skid roads were converted into riding and carriage trails. Martin Wunderlich bought the property from the Folgers in November 1956 and in 1974 deeded 942 acres to San Mateo County for park and open space. That lineage is why Wunderlich still centers on the Folger Stable and its horse-friendly grades, while Huddart's creek-side picnic areas, restrooms with tie racks, ride-in access from surrounding Woodside Trails, and the wider Richard's Road with long sight-lines for a safe trot or canter read more like a shaded park for families and group gatherings.
The practical read for a resident planning a Saturday: Wunderlich if you are going up and want quiet, Huddart if you are bringing the family and the coolers.
What is actually on the ridge calendar
Fogarty publishes a slim events calendar rather than a run of weekend openings, and two late-August dates are worth putting on the fridge.
- Saturday, August 22, 2026. An afternoon in the mountains pairing Choco Del Mar artisan chocolate with Fogarty red wines.
- Sunday, August 30, 2026, 2:00 to 4:00 PM. A sound bath led by Paula Sockolich of Sacred Lotus Healing, $75 per ticket.
For anyone who has not visited in a while, the standard drop-in still holds. Tastings start at $20 for a Bar Splash, and reservations are recommended. One note that saves twenty minutes: the winery advises against approaching by Old La Honda Road. That advice has more weight this year than usual, and there is a reason, covered below.
The village at sea level
Coming off the ridge, the town center compresses a full weekend's worth of stops into a quarter-mile of Woodside Road. The order most residents use is unspoken but consistent.
Coffee first, at The Village Hub Coffee Bar at 3154 Woodside Road. Then the counter that has anchored the town longer than any other business: Roberts Market, established in 1889, offering bakery, deli, produce, wine, meat and grocery items. Its 3015 Woodside Road address and 6:30 AM to 8:00 PM daily hours mean that a picnic for the trail can be assembled at almost any hour a hiker would want to leave.
For a sit-down lunch or dinner, Buck's at 3040 Woodside Road is the one non-locals recognize by name and locals treat as a neighborhood room. And when the weekend calls for a longer drive up the hill, Sky Londa's "Four Corners" at the intersection of Highways 84 and 35 offers gas, groceries at Roberts Market, and dining at Alice's Restaurant.
The efficient move on a Saturday morning: coffee at Village Hub, sandwiches and a pastry from the Roberts deli, park at Wunderlich by 9:00 AM, climb the Alambique Trail to The Crossroads, and be at Fogarty by early afternoon. The whole loop stays inside Woodside's borders.
Two logistics worth tracking this month
The town has two active items that will shape how residents move through August and September, and neither shows up on the standard neighborhood guide.
The first is a road project on the western approach. The town's contractor, Altor Construction, began drainage improvements on Old La Honda Road on March 3, 2026, in the public right of way between 207 Old La Honda Road and 320 Old La Honda Road, with no full road closures planned but lane closures and flaggers producing minor delays for motorists and cyclists. If you are cycling the classic Old La Honda climb or driving up to Fogarty, take Woodside Road to Skyline instead. That is the same advice the winery itself gives.
The second is the leaf blower ordinance that quietly changed daily life this summer. The Town of Woodside's leaf blower regulations took effect July 1, 2026 and prohibit the use of gas-powered leaf blowers in specific zoning districts. There is a rebate program worth knowing about if you have not yet swapped equipment or briefed your landscaper: residents can apply for a free electric leaf blower kit or a $250 voucher, and landscaping businesses and properties over five acres can apply for a $1,000 voucher for electric garden equipment. The practical effect on a Saturday morning is audible. The town is quieter now than it was in June, and residents who work from home have noticed first.
Why the two-elevation frame matters
A generic weekend guide would list these places as parallel options. That is the version of Woodside that appears on travel sites, and it misses what makes the town legible to the people who live here.
The redwood-shaded canyons and the sun-lit ridge are not competing destinations. They are a single vertical route that a resident can traverse in one morning. The parks were assembled from ranch land that once produced the wagon roads still used as trails. The winery was planted on the ridge those wagons climbed toward. Roberts Market has been provisioning the whole picture since 1889. Old La Honda Road, currently under repair, is the seam that ties the ridge to the valley floor and to Portola Valley beyond.
Read Woodside vertically and the calendar organizes itself. Read it as a flat list of amenities and you end up doing one thing at a time.
If you are thinking about how a home here would actually be lived in, whether that means selling a property that has watched this cycle for thirty years or acquiring one you plan to keep for the next thirty, Dana Rae Stone knows this ground at both elevations. Let's talk about your home.
