Windy Hill is named for its distinctive, breezy grass-covered hilltop, which can be seen from many areas of the peninsula. The 1,335-acre preserve features open grassland ridges and forests of redwood, fir, and oak.
The Peninsula Open Space Trust, a local nonprofit land trust, provided major support for acquisition of this preserve.
Temporary COVID-19 Restrictions
Hikers
Hikers at Windy Hill Preserve. Photo byJack Gescheidt
oak tree
Oaks are part of the landscape at Windy Hill Preserve. Photo by Karl Gohl
hemlock
A field of hemlock at Windy Hill Preserve. Photo by Karl Gohl
view from Windy HIll
A view of the valley below from Windy Hill. Photo by Midpen
windy hill dog
Dogs are welcome on most trails at Windy Hill Preserve. Photo by Deane Little
Windy Hill Open Space Preserve is located in the Town of Portola Valley.
Lower Windy Hill
The parking lot at the lower portion of the preserve is located on Portola Road. Parking is available for 25 vehicles. Please note: This parking lot fills quickly. Please do not park on Portola Road: parking is strictly enforced.
Overflow parking is available at the Portola Valley Town Center, approximately 0.4 miles north on Portola Road. Take the Portola Trail from the Town Center to the Windy Hill parking lot.
Get driving directions to main lot:
Equestrian trailer/bus parking
Equestrian trailer/bus parking is available, courtesy of the Town of Portola Valley, at the driveway entrance to the Spring Downs Equestrian Center at 725 Portola Road. The driveway off Portola Road is town property, and there is a gravel area to the left of the paved driveway that is suitable for trailer/bus parking. A ½-mile roadside trail runs from the driveway to the Windy Hill parking lot on Portola Road. Please note: Spring Down is a private facility, and Midpen visitors should not enter that area.
Get driving directions to equestrian parking:
Upper Windy Hill
Parking for the upper portion of the preserve, the Skyline Boulevard Picnic Area, is located on Skyline Boulevard (Highway 35), 2.3 miles south of Highway 84 (La Honda Road) and 4.9 miles north of Page Mill Road. Additional roadside parking is available along Skyline Boulevard.
Get driving directions to Skyline Boulevard Picnic Area:
Hikers and equestrians use the Hamms Gulch, Eagle, Razorback Ridge, and Lost Trails to make an 8-mile loop through forested ridges to the valley floor and back again.
The Anniversary Trail provides a short hike atop Windy Hill, with spectacular views of the bay and surrounding valley.
Popular among bicyclists is the Spring Ridge Trail, which descends from Skyline Boulevard and continues along a grassy ridge to Portola Valley.
Dogs - Leashed dogs are allowed on all trails except Lost and Razorback Trails. (Dogs are allowed on the portion of Lost Trail between the Hamms Gulch Trail and the Anniversary Trail).
This information is updated as needed when trails are opened or closed, or when there is scheduled trail maintenance. Visit the full Trail Conditions page for more information.
The following trails may be closed to equestrian use during wet conditions.
Recognized as a significant addition to Midpen in 1980, Windy Hill Preserve was formed in the "upper" portion with a 537-acre acquisition with major support from the Peninsula Open Space Trust. A second major purchase of 429 acres in 1987 added the "lower" portion and included the scenic backdrop of Spring Ridge.
Windy Hill is named for its distinctive, breezy grass-covered hilltop, which can be seen from many areas of the peninsula. The 1,335-acre preserve features open grassland ridges and forests of redwood, fir, and oak.
The Peninsula Open Space Trust, a local nonprofit land trust, provided major support for acquisition of this preserve.
Temporary COVID-19 Restrictions
Windy Hill Open Space Preserve is located in the Town of Portola Valley.
Lower Windy Hill
The parking lot at the lower portion of the preserve is located on Portola Road. Parking is available for 25 vehicles. Please note: This parking lot fills quickly. Please do not park on Portola Road: parking is strictly enforced.
Overflow parking is available at the Portola Valley Town Center, approximately 0.4 miles north on Portola Road. Take the Portola Trail from the Town Center to the Windy Hill parking lot.
Get driving directions to main lot:
Equestrian trailer/bus parking
Equestrian trailer/bus parking is available, courtesy of the Town of Portola Valley, at the driveway entrance to the Spring Downs Equestrian Center at 725 Portola Road. The driveway off Portola Road is town property, and there is a gravel area to the left of the paved driveway that is suitable for trailer/bus parking. A ½-mile roadside trail runs from the driveway to the Windy Hill parking lot on Portola Road. Please note: Spring Down is a private facility, and Midpen visitors should not enter that area.
Get driving directions to equestrian parking:
Upper Windy Hill
Parking for the upper portion of the preserve, the Skyline Boulevard Picnic Area, is located on Skyline Boulevard (Highway 35), 2.3 miles south of Highway 84 (La Honda Road) and 4.9 miles north of Page Mill Road. Additional roadside parking is available along Skyline Boulevard.
Get driving directions to Skyline Boulevard Picnic Area:
Hikers and equestrians use the Hamms Gulch, Eagle, Razorback Ridge, and Lost Trails to make an 8-mile loop through forested ridges to the valley floor and back again.
The Anniversary Trail provides a short hike atop Windy Hill, with spectacular views of the bay and surrounding valley.
Popular among bicyclists is the Spring Ridge Trail, which descends from Skyline Boulevard and continues along a grassy ridge to Portola Valley.
Dogs - Leashed dogs are allowed on all trails except Lost and Razorback Trails. (Dogs are allowed on the portion of Lost Trail between the Hamms Gulch Trail and the Anniversary Trail).
This information is updated as needed when trails are opened or closed, or when there is scheduled trail maintenance. Visit the full Trail Conditions page for more information.
The following trails may be closed to equestrian use during wet conditions.
Recognized as a significant addition to Midpen in 1980, Windy Hill Preserve was formed in the "upper" portion with a 537-acre acquisition with major support from the Peninsula Open Space Trust. A second major purchase of 429 acres in 1987 added the "lower" portion and included the scenic backdrop of Spring Ridge.
Preserves are open from one-half hour before official sunrise until one-half hour after official sunset.
There are no events scheduled at this preserve currently.