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

Hiking Forecast: Windy

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

Woman hiking at Windy Hill Preserve

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!

Trending Stories NorCal

View all Stories
  1. Muir Woods Night Tour

    Thousands of people flock to Muir Woods every year, yet only a few see it at night, when this beloved park is experienced in a whole new light. The Muir Woods Night Tour happens on the last Friday of every month through October.

    View
  2. Slide Ranch Marin

    Slide On Over

    Marin's Slide Ranch has a popular neighbor in the Muir Beach Overlook. But don’t overlook Slide! This open-to-the-public nonprofit organization sits on 134 acres of coastline and is filled with animals, Pacific scenery, and an adjacent hiking trail.

    View
  3. Sponsored

    Take the Exit to the Best of the San Francisco Peninsula

    The San Francisco Peninsula is proof that some of Northern California’s greatest surprises are hiding just off Highway 101. All you have to do is take the exit.

    View
  4. Hello, Sur!

    Big Sur is home to numerous fantastic beaches and coves, so which one do you choose? Go for the beach that's quintessential Big Sur (and dog-friendly!). Pfeiffer Beach in Pfeiffer Big Sur State Park. Its signature lilac-colored sand is waiting for your feet!

    View

Trending Stories SoCal

View all Stories
  1. Waterfall Hunter

    If you ask a local in Reno about one of the best hiking trails in town, odds are high they’ll point you to Hunter Creek Falls. It’s a year-round favorite, but it absolutely shines in spring, when desert peach wildflowers make a splash—and so does the marquee waterfall.

    View
  2. Wapama Wows

    Hetch Hetchy can be overlooked in Yosemite National Park because of its more remote location and limited facilities. But this is where you’ll also find one of the best day hikes in the park: Wapama Falls.

    View
  3. Bike the Coastal Trail to Pillar Point Harbor in Half Moon Bay

    Ride and Seek

    Oceanside breezes, beautiful beaches, a car-free pathway for biking, and beer at the end: You’re on a roll! The San Mateo Coast was made for beach hopping and beer tasting … and it all goes down smooth as part of an 8-mile out-and-back bike ride.

    View
  4. Tamtastic Sunset

    Sure, the East Peak of Mount Tam is absolutely spectacular at sunset, but some magic-hour enthusiasts are onto a fresh perspective in getting a little more personal space for their panoramic viewings.

    View