Windy Hill: Open in the Hills of San Mateo County

Windy Hill in 2015.

Windy Hill in 2015. This 1,335-acre preserve is sure to satisfy hikers, bikers and horse back riders.

Windy Hill Open Space Preserve is part of a myriad of open spaces found in the hills of San Mateo County, California. Located between Skyline Boulevard (Highway 35) and I-280, the forested hills and open grasslands of Windy Hill have twelve miles of sense-satisfying trails with spectacular views of the bay and Pacific Ocean. Hikers, bikers and horse back riders are not the only ones who have admired this place. Mexican rancheros, European ranchers and citizens of Portola Valley have made their mark on Windy Hill.

Named for the Wind

According to Jimmy Rapley, an old mountain cowboy, government surveyors needed a name for this prominent grassy mound. He couldn’t recall ever hearing a name, but volunteered that it was where the wind blows over the ridge, and so it became Windy Hill. If you are visiting, you may see an occasional hang glider soaring in the strong wind currents on the eastern slope of the hill.

Mexican Rancho

In the Mexican era, the summit near Windy Hill formed the boundary of a rancho granted to Maximo Martinez. Damiana Gulch is named for Martinez’ wife. Damiana is the common name for a shrub found in Central America whose leaves were sometimes brewed for an aphrodisiac. Proving to the plant’s name, Damiana bore fifteen children in her 87 years of life.

Maximo and Damiana Martinez who occupied the Mexican rancho El Corte de Madera. Courtesy of Portola Valley archives.

Maximo and Damiana Martinez who occupied the Mexican rancho El Corte de Madera. Courtesy of Portola Valley archives.

The Boulevard Plows through History

Steam shovels and powder monkeys, with their black powder, plowed through these hills in the construction of Skyline Boulevard in the late 1920s and disrupted the heart of the Brown Ranch. If you happen to be visiting, look out for several large cuts along the highway that were left in the creation of the boulevard. Remnants of an old quarry, represented as odd shaped bumps and hollows on the horizon, lay south having been used to fill in Skyline Boulevard in the late 1920s

The old Brown ranch during the construction of the boulevard. Note the wide open pasture land, now being filled in with coyote brush.

The old Brown ranch during the construction of the boulevard. Note the wide open pasture land, now being filled in with coyote brush.

In a previous life, the Brown ranch had played host to an illegal still in Prohibition days. In the 1860s it was a small summer resort run by the Hamms who took advantage of the great vistas and their location on a turnpike between Redwood City and San Gregorio to cater to travelers.

The old quarry used in the construction of Skyline Boulevard.

The old quarry used in the construction of Skyline Boulevard.

Read the rest of the story here at mobileranger.com to find out how Windy Hill dodged housing plans and became an open space preserve.

Take the Self-Guided Mobile Tour

This piece is part of a tour all about South Skyline Boulevard by The Skyline Historical Society. Download the free app with many tours of the Santa Cruz area and beyond.

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Julia Gaudinski


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