Windy Hill Walks

Jan 24th, 2019

Windy Hill Preserve
Named for its distinctive and breezy grass-covered hilltop, Windy Hill Preserve features 1,335-acres of open grassland ridges and forests of redwood, fir, and oak. Aptly named, Windy Hill is great for kite flying–you may even see some paragliders along your hike. Cap off your adventure at the preserve’s picnic tables, perfect for a post-hike or ride gathering.

Windy Hill Summit
County: San Mateo
Distance: 3.2 miles (6.4 miles out & back)
Difficulty: Moderate
Follow the Windy Hill ridgeline through a sheltered forest and across rolling grasslands on a narrow footpath and broad wagon road. After initially descending, you gradually gain 234 feet on a final short climb to the knobs of Windy Hill–a peninsula landmark. Your climb will be rewarded with sweeping views of the San Mateo Coast and the Santa Clara Valley.

Directions: Starting at the Razorback Ridge Trailhead, follow Razorback Ridge Trail 0.3 miles to the Lost Trail. Continue on the lost trail for 2.3 miles to the Anniversary Trail. Follow the Anniversary Trail for about 0.5 mile to reach the Windy Hill summit trail. Return back the way you came.

Make it a loop…
After you’ve summited, keep the adventure going and extend your hike another half mile and make it a loop.

Directions: Starting at the Windy Hill Summit, return to theAnniversary Trail and follow it north 0.5 miles. Continue south on the Fence Trail (which connects to the Anniversary trail just before you reach the Spring Ridge parking lot) for 0.5 miles. Continue on the Lost Trail back to the Razorback Ridge Trailhead.

Make it a mini-loop…
Looking for something a little shorter? Start your adventure at the Anniversary Trailhead. Find a place to fly a kite, climb up to the Windy Hill summit, and cap it off with a post-hike bite at the trailhead’s picnic area.

Directions: Starting from the Anniversary Trailhead, follow the Anniversary trail 0.5 miles to the Windy Hill Summit Trail. Return to the Anniversary Trail and follow it north 0.5 miles. Continue south on the Fence Trail (which connects to the Anniversary trail just before you reach the Spring Ridge parking lot) for 0.5 miles back to the Anniversary Trailhead and picnic area.

Windy Hill Map
Windy Hill Open Space Preserve Map

Refuel at some of our favorite nearby spots
Take the scenic route back to SF along Skyline Boulevard and stop at the famed Alice’s Restaurant in Woodside. There is plenty of seating out back and on the side, complete with horseshoe pits and plenty of space for little ones to run around while you enjoy a cold post-hike brew. It does get hectic with bikers on the weekends.

Or stop by Portola Valley’s historic Alpine Inn and grab a brew in their outdoor beer garden. And if you are in the mood for a sweet treat, don’t miss the Tin Pot Creamery in nearby Los Altos.


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