Hiking Forecast: Windy

Hike and Watch a Sunset at Windy Hill Preserve in the South Bay

Autumn’s hues may not be in full swing but give it time and they'll be fully showing off thanks to the big-leaf maples at Windy Hill Preserve in the South Bay. We recommend a 6.2-mile loop that starts and finishes at one of the Skyline Boulevard staging areas (there are two staging areas within a mile of each other). The reason? You’ll end at the preserve’s namesake hill, where sunset views dazzle.

If you park at the second staging area (about a half mile farther south from the first staging area on Skyline Boulevard) you’ll begin your hike on the Anniversary Trail and wind half a mile up Windy Hill before connecting to the Spring Ridge Trail. If you park at the first staging area, you’ll be at Spring Ridge Trail and begin an immediate descent on a wide dirt trail where the grassy hills roll all the way out to impressive views of the Diablo mountain range.

The Meadow Trail connects hikers to Hamm’s Gulch Trail and the fabulous foliage of fallen leaves carpeting the earth in brown, amber, and green hues. Thank the big-leaf maples for the color-fall parade as you begin a steady but gradual 3.5-mile ascent through the fragrant forest. It’s a workout.

Woman hiking on the trail at Windy Hill Preserve

Time your hike to finish the loop about 45 minutes ahead of sunset. The grand finale is the apex of Windy Hill itself, hands down one of the Bay Area’s finest points for catching a sunset.

The western views of the Santa Cruz Mountains look dusted in gold, followed by the sky shifting colors from burnt orange to hot pink. Sunsational!

For this hike, and to catch sunset after, we recommend parking at the Skyline Blvd. (Hwy. 35) staging area (map). Start on the Anniversary Trail going north toward the summit. Make a clockwise loop connecting Spring Ridge Trail, Meadow Trail, Hamms Gulch Trail, and Lost Trail. Windy Hill lives up to its name, so dress accordingly! Dog-friendly!

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