First Footsteps
Windy Hill
A pocket-sized summit adventure from Skyline, with a longer Portola Valley loop for another day.
Quest challenge 1/10 · First Adventure
Quest estimate for the described approach: endurance, altitude, and technical terrain combined. Conditions can change the difficulty. This is not an AllTrails or climbing grade.
Meet the mountain
The approach: Anniversary Trail and summit spur from Skyline Boulevard
Summit finish: Windy Hill’s summit via the designated spur.
A small summit with a big Bay-and-Pacific outlook—a fine first chapter in your trail journal. Start at the upper Skyline parking areas for the short Anniversary Trail approach. The 7.2-mile lower-preserve loop is a different, longer day. Choose the summit spur rather than finishing only at a roadside overlook.
Pick the trailhead that matches the day you want; keep to designated trails.
A SUMMIT QUEST TALL TALE · FICTION
The wind’s unfinished sentence
A breeze came here to make one quick announcement and lost its place. It has been clearing its throat ever since. The grass remains a patient audience.
Explore the Field Guide’s peak legends →Before you set out
Every good quest starts with a little map time. Explore these route guides and check the latest updates before setting a date.
Sources reviewed 2026-09-08. Check the links for current conditions. The approach above explains our challenge rating; logging this peak does not assign that route to your outing.
Midpen Windy Hill preserve ↗
Preserve map, summit access, and longer loop options.
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Search for an approach that matches your plan.
Opens in a new tabFind recent trip reports ↗
Check dates and route choices; reports do not replace current land-manager information.
Opens in a new tab“Find AllTrails routes” opens a Google search restricted to AllTrails trail pages, not a selected route. Completion is tracked in Summit Quest and does not sync with AllTrails.