Visit Woodside, California: Redwoods, Estates & Ranch Roads

A 1917 Georgian Revival estate with 16 acres of formal gardens, one of the finest country houses in California, open to visitors most of the year.

Redwood and oak trails climbing the eastern slope of the Santa Cruz Mountains, with picnic meadows and a link to the Skyline Trail.

Former estate land with redwood groves, old carriage roads and views across the bay from The Meadows.

A hilltop winery on Skyline Boulevard with tastings of Santa Cruz Mountains pinot noir and chardonnay and wide views over the valley.

The oldest surviving store building in San Mateo County, now a small museum on the logging and ranching history of the area.

Filoli Historic House & Garden is the reason most people drive out to Woodside. The 54,000-square-foot Georgian house sits in 16 acres of formal gardens, and those gardens sit inside a 654-acre estate at 86 Cañada Road. Admission runs from 10am to 5pm daily and parking is free. Spring brings 130,000 flowering bulbs; autumn brings Orchard Days; the house is decorated from mid-November through early January.

Two San Mateo County parks cover the hillsides above town. Huddart Park has 973 acres of second-growth redwoods, creeks and picnic meadows, with trails for most fitness levels. Wunderlich County Park climbs from oak woodland into redwoods and holds the restored Folger Estate Stable, still a working stable with a small museum in the old carriage room. Both parks allow hiking, riding and, on marked trails, mountain bikes.

Woodside is where a large share of Bay Area cycling starts. Old La Honda Road climbs about three miles and 1,295 feet from the bridge up to Skyline Boulevard at roughly an 8% grade, and it is one of the most ridden segments in the region. Kings Mountain Road makes the standard descent back into town, narrow and twisty at about 7.5% average. Expect company on Saturday and Sunday mornings.

Thomas Fogarty Winery sits high on Skyline Boulevard and pours Pinot Noir and Chardonnay with the whole Bay laid out below. Down in the village, food in Woodside runs from breakfast at Buck's, a diner that has hosted decades of venture capital meetings, to dinner at The Village Pub. Roberts Market and the Village Bakery cover picnic supplies before a hike.

The oldest and grandest part of town, where Mountain Home Road and its side lanes run past paddocks, white fences and long private drives. Properties here are large and mostly hidden from the road, with views out to the foothills and open space. There is nothing to buy and nothing to queue for, which is the point: this is the stretch people drive or ride slowly for the scenery.

The Glens started out as vacation cottages and housing for staff on the big estates, and the small lots and narrow lanes still show it. It is the one part of Woodside where you can walk to the village, which makes it the easiest base if you would rather leave the car parked. Cyclists heading for Old La Honda Road pass through constantly.

Kings Mountain Road switchbacks up through redwoods from the village to Skyline Boulevard, past Huddart Park and a scatter of cabins and mailboxes on the shoulder. Cyclists use it as the descent at the end of a Skyline loop, so drivers should take the blind corners slowly. The road is also the access point for the northern Huddart Park trailheads.

Up on the western edge of town, Skywood runs along Skyline Boulevard with houses on big wooded lots and views over the Bay. Sky Londa, the junction of Skyline and La Honda Road, is where Alice's Restaurant draws cyclists and motorcyclists all weekend. From here it is a short drop down Highway 84 to the coast.

We recommend: Filoli plus the village

We recommend: gardens, redwoods and the ridge

We recommend: the Old La Honda and Kings Mountain loop

We recommend: horses, redwoods and picnics

Twenty-two miles and about 35 minutes west over Highway 84, with a harbor, a long beach walk at Pillar Point and pumpkin farms along the approach road in October. The drive down through La Honda is half the reason to go.

Under half an hour east. The Stanford campus is open to visitors, with Hoover Tower, the Cantor Arts Center and the Rodin sculpture garden, and University Avenue nearby for lunch and bookshops.

Around 30 miles north, 40 minutes by car or an hour door to door using Caltrain from Redwood City. Close enough that plenty of people base themselves in Woodside and treat San Francisco as the day out.

An hour over the hills on Highway 84, through La Honda and out to farm stands, artichoke bread at the general store and a stretch of coast with very few people on it.

About an hour and a quarter south, either down Interstate 280 and Highway 17 or the slower way along Skyline. The boardwalk, the wharf and Natural Bridges make it an easy full day with children.

Head south along Skyline Boulevard for the open-space preserves on the ridge, then drop into Portola Redwoods State Park for old-growth groves and a quieter alternative to the county parks.