The Wind Beneath Your Feet
Do the Short Hike to Panoramic Views at Windy Hill on the San Francisco Peninsula
The perfect way to wind down a day on the San Francisco Peninsula might just be a late afternoon or sunset-hour hike to one of the region’s premier vista points: Windy Hill.
Park at the second staging area (about a half-mile south of the first staging area on Skyline Boulevard) and begin a short hike on Anniversary Trail, gently winding just over half a mile to the summit.
When you arrive, take a spin and soak in the 360-degree views. Windy Hill’s location—smack between the Pacific and Silicon Valley—makes it one of the Peninsula’s best sunset spots. During the magic hour, watch the sun ignite everything from the ocean to Mount Diablo. To the west, the Santa Cruz Mountains glow gold before the sky shifts from burnt orange to hot pink. Oh hill yeah!
PRO TIP: Near the top, before reaching Windy Hill's official summit, there's a sign to the Herb Grench Overlook. This 0.1-mile trail leads to a similar overlook, but has a lone bench quietly waiting. For you?
Park at the Skyline Boulevard (Highway 35) staging area and begin on Anniversary Trail heading north toward the summit. Windy Hill lives up to its name, so bring an extra layer. Dog-friendly!
