Top Outdoor Activities in Woodside, CA

Woodside, Calif., is bordered by redwood forests, open ridgelines, and scenic valleys below Skyline Boulevard. Outdoor activities in Woodside reflect this connection to land and landscape. The proximity to Wunderlich Park, Huddart Park, and Edgewood Preserve gives locals year-round access to well-maintained trails and forested environments. Quiet roads support cycling and scenic driving, while local parks and gathering spaces offer more casual public use. Equestrian routes are integrated into town planning and remain a central feature of daily life.

Wunderlich County Park includes over 900 acres of wooded hillsides, redwood groves, and open ridges. The park entrance is located directly on Woodside Road, just west of town, with a gravel parking lot and detailed trail maps. Trails range in elevation and distance, with routes like the Bear Gulch Trail and Alambique Trail offering steady climbs through second-growth redwoods and shaded oak canopies.

At higher elevations, views open up toward the Santa Cruz Mountains and the Bay. The Madrone and Meadow Trails create lower-elevation loops suitable for shorter hikes. Equestrians and hikers share most routes, and trails are wide enough to accommodate both. The park is busiest on weekends, but weekday mornings offer quiet conditions and consistent trail maintenance.

Woodside maintains one of the most extensive networks of publicly accessible horse trails in the Bay Area. The town includes designated bridle paths that run alongside roads, behind fences, and into connected preserves. Equestrian culture is built into the town’s identity, and many properties include stables and direct access to these trails. Riders can leave from home and reach areas like Wunderlich, Huddart Park, or the surrounding fire roads without using trailers.

Local equestrian centers such as The Horse Park at Woodside support daily riding, training, and competitions. These facilities include outdoor arenas, jump courses, and access to longer trail routes. Residents and visitors using these trails follow posted guidelines for right-of-way and seasonal conditions.

Skyline Boulevard and Kings Mountain Road are key routes for road cyclists in Woodside. These roads offer long, steady climbs with limited traffic and broad views of the surrounding hills. Kings Mountain Road connects Highway 84 to Skyline Boulevard and includes multiple switchbacks through redwoods. Riders use this climb for fitness and training, especially early in the day.

Skyline Boulevard runs along the ridge with pullouts and rest spots near trailheads. The road’s elevation and smooth surface make it popular with cyclists from the coast and the peninsula. Loop options include dropping into La Honda or descending into Portola Valley. Riders usually start at the junction near Roberts Market or park near Huddart Park.

Huddart Park includes several interconnected trails that support trail running on shaded dirt paths. The Crystal Springs Trail, Dean Trail, and Richards Road Trail create longer loops with steady elevation and minimal road crossings. Trail runners use these routes for midweek training and weekend distance runs. The terrain includes forested slopes, creek crossings, and soft trails that drain well after rain.

The park has multiple access points, but most runners start at the Kings Mountain Road entrance. A small parking fee is charged at the gate, and restrooms and water are available at trailheads. Some routes climb over 1,000 feet in just a few miles, offering an intense workout and quiet surroundings. The limited number of weekday users makes this one of the better places to train without crowding.

Barkley Fields and Park is one of the few flat, open spaces in the town center. It is located behind the Woodside Town Hall and adjacent to the Community Museum. The park includes picnic tables, a turf field, and shade trees, supporting low-key recreation and casual meetups.

The location is easily accessible on foot or by bike from the central part of town. Parking is available along Woodside Road. The park is also used during town events, including concerts and seasonal festivals. The space is maintained by the town and remains in use year-round. Residents use the field for yoga, catch, and informal soccer or frisbee.

Filoli, located just south of central Woodside off Cañada Road, includes more than 600 acres of gardens, trails, and historic architecture. While the main house and formal gardens require paid admission, the surrounding estate trail system supports walking and light hiking through meadows and oak woodland. The trail system is open seasonally and includes views of the reservoir and distant ridges.

Visitors often combine a walk with a visit to the garden or a stop at the on-site café. The estate trail is a lower-impact option compared to the steeper terrain of the nearby county parks. This location is used frequently by residents with memberships who return weekly or seasonally to track changes in the landscape.

Woodside includes scenic roads that wind through redwood forest, open pasture, and ridgelines. Portola Road, Highway 84 (La Honda Road), and Cañada Road offer views of horse farms, open ridgelines, and distant mountains. These roads are used for slow weekend drives, photo stops, or as access to trailheads and open space.

Cañada Road includes a segment that closes to vehicle traffic on weekends, creating a car-free zone for walking and biking. This route passes Crystal Springs Reservoir and includes broad shoulders and long straightaways. Scenic driving is often paired with stops at trailheads, lookouts, or casual restaurants in La Honda or Skylonda.

Edgewood Park is located just outside Woodside’s eastern edge and includes more than 450 acres of open hillsides, oak woodland, and wildflower-covered slopes. Trails such as the Edgewood Trail and Serpentine Trail offer moderate loops with elevation gain and clear views toward the Bay. The preserve is known for its native plant diversity and quiet trail system.

Walkers use Edgewood for nature-focused outings. The preserve includes interpretive signs, birdwatching platforms, and shaded benches. Parking is located at the Old Stage Day Use Area, and trails connect easily into longer loops. Wildlife sightings often include deer, hawks, and seasonal bird migrations.

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