Windy Hill is named for its distinctive, breezy grass-covered hilltop, which can be seen from many areas of the peninsula. The 1,414-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.
This 0.6-mile trail spans between the two Windy Hill parking lots on Skyline Boulevard, and includes detours to the summit of Windy Hill, as well as the Herb Grench overlook. This short walk provides a 360-degree panorama, with views of both the San Francisco Bay and the Pacific Ocean. Turn this trail into an approximately one-mile loop by returning to the parking lot via the disc track along Skyline Boulevard.
This 1.6-mile long loop is suitable for users of various skill levels, with a total elevation gain of 200 feet. As you walk this trail, you will pass through oak woodlands, as well as open, grassy meadows that display beautiful wildflowers in the spring. The highlight of this trail is of course Sausal Pond. At the pond, you may be treated to sights of egrets, blue herons, wood ducks, dragonflies, or even the western pond turtle, which is a California species of special concern.
Stay on designated trails and observation areas to help protect the fragile environment around the pond. Dogs are able to use this trail, but must be kept on-leash.
This 7.2-mile loop will take you through all of the highlights of the Windy Hill Preserve as you traverse the Spring Ridge Trail, Lost Trail and Hamm’s Gulch Trail. You will pass by Sausal Pond, and through several different habitat types including oak woodlands, chapparal, and grassy meadows. This loop will also take you to the iconic summit of Windy Hill where — fog permitting — you will be able to see both the Bay, and the Pacific.
Preserve Highlights & Features
Kite Flying and Hang Gliding
Windy Hill is an ideal spot for kite flying.
It's also a northeast-facing paragliding and hang gliding site! Excellent pilot judgement and skills are required to in order fly this location safely. Access and permits are managed through the Windy Hill Skyriders, a chapter of the United States Hang Gliding and Paragliding Association.
Picnic tables are located adjacent to the Spring Ridge parking area – a super beginning to a day or the perfect ending to a long hike or kite flying session!
Stories from the Preserves
Here are some of the plants and animals that other visitors have observed at this preserve and recorded in iNaturalist. Protected species may be excluded and some species may not yet have been observed. Help improve iNaturalist by adding your observations to the Midpen Biodiversity Index project
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Know Before You Go
Preserve regulations help provide a safe, enjoyable visit while protecting sensitive areas and wildlife.
Share the Trail
Use designated trails to avoid damage to natural resources and prevent injury.
Avoid blocking the trail. Step aside to allow others to pass .
Whether you’re walking or biking, always yield to equestrians.
Leave no trace. Pack out what you pack in. Most preserves do not have trash cans. Littering is prohibited.
Abuses of trail etiquette should be brought to the attention of a ranger or call the Midpen main office at 650-691-1200.
The following trails may be closed to equestrian use during wet conditions.
- Betsy Crowder Trail is OPEN to equestrians.
- Hamms Gulch Trail is OPEN to equestrians.
- Lost Trail is OPEN to equestrians.
- Razorback Ridge Trail is OPEN to equestrians
Lower Windy Hill (49 spaces): The parking lot at the lower portion of the preserve is located on Portola Road. 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.
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.
Upper Windy Hill (12 spaces): 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.
- Bicyclists: Bicycles are allowed on designated trails only (marked on map). Helmets are required. Observe the 15 mph trail speed limit (5 mph when passing). Avoid startling hikers and equestrians by announcing your presence when approaching from behind.For more information visit the Bicycle Access page.
- Dogs: Dogs are allowed only on designated trails in this preserve (marked on map) and must be controlled on a 6-foot or less leash. Self-retracting leashes are allowed with a maximum extended length of 25 feet. Visitors may have no more than three dogs per person. Bag dog waste and take it with you. Midpen accommodates service dogs in preserves wherever we allow public access. For more information visit the Dog Access page.
- Equestrians: Horses are allowed on designated trails (marked on map). Helmets are recommended for all equestrians. For more information visit the Equestrian Access page.
- Fires are prohibited in preserves.
- Plants & Wildlife: Please leave undisturbed. If you encounter wildlife during a visit, do not approach, startle or feed it. Although wild animals are generally fearful of humans and will run away, some wildlife can be dangerous.
- Smoking is prohibited in preserves.
- Water Areas: Swimming, wading or engaging in any water-contact activity is prohibited.
- Weapons are prohibited in preserves.
A general access permit is required for any activity or event that:
- may be attended by twenty (20) or more people; OR
- would restrict the use of any part of Midpen lands by members of the public; OR
- requests or requires a fee be paid or a donation made for participation. This includes events where the fee is in the form of a mandatory purchase, such as a t-shirt.
Hang gliding, paragliding, and remote control gliding are allowed by obtaining a special activity permit.
Midpen trails and facilities are generally very safe. However, you are entering an environment where there are some naturally occurring hazards. Reasonable caution and common sense should be utilized when venturing into any outdoor environment.
- Do not leave valuables in your vehicle! Lock your vehicle and store valuables out of sight or take them with you on the trail.
- Travel in groups of two or more. Two of more people can assist each other in the event of an accident or emergency.
- Dress for the environment. Temperature changes can be occur and you should dress in layers appropriate for the location, time of year and planned activities.
- Carry water with you. Drinking water is not available at most Midpen preserves so you should bring your own. Two quarts per person per two hour hike is recommended.
- Apply sunscreen and drink plenty of water prior to and during your outdoor activities.
- Be aware that cell service is very sporadic on the preserves.
Be Prepared and Aware
Plan ahead before you leave. Check regulations and weather, download a map, pack water and first aid.
Know your limits and take safety precautions.
Rattlesnakes are native to this area and are especially active in warm weather.
Poison oak grows on most preserves: Learn to identify and avoid it in all seasons.
Ticks are present in this area and may carry diseases.
Mountain lions are a natural part of this region’s environment and are occasionally seen.
In Case of Emergency
If you experience an emergency (fire, accident or other immediate threat to life or property), call 911. For nonemergencies, call 650-691-1200.
Activities & Events
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.