Gone With the Windy

Watch a sunset at Windy Hill Open Space Preserve in Portola Valley

02.10.2021
Man standing at Windy Hill and watching a fiery sunset at Windy Hill Preserve

You don’t have to trek far to enjoy a hiker’s high on the Peninsula’s Windy Hill Preserve. Its panoramic attraction—Windy Hill—is easily accessed via the 0.7-mile Anniversary Trail. And it’s magnificent at sunset.

When you reach the summit, spin to the 360-degree views. Windy Hill’s location, smack between the Pacific and Silicon Valley, makes it an ideal spot on a clear evening. You can watch the sun ignite everything from the ocean to Mount Diablo. 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!

Woman watching a sunset atop Windy Hill at Windy Hill Preserve on the Peninsula

TIP: For those who want a longer hike, followed by sunset viewing at Windy Hill, this 6.2 mile loop hike hits some high notes with views, with forest enjoyment too.

On Skyline Blvd. (Hwy. 35), drive about 2 miles south of Hwy. 84 (La Honda Rd.). The parking area and Anniversary Trail are on the east side of the road. Note: Prepare for potentially gusty conditions by bringing extra layers. Dog-friendly!

Trending Stories NorCal

View all Stories

  1. Sunnyvale and Salty

    For up-close bird watching, it’s hard to beat a walk along the San Francisco Bay. This 5-mile loop on the Sunnyvale coast is a favorite of local wildlife photographers.

    View
  2. A man takes a break at a temple spot on a hike at Dragon Mountain in Milptas

    Dragon Quest

    The newly reopened, 4-mile out-and-back hike at Dragon Mountain in Milpitas mixes the physical with the spiritual for a serene hiking experience.

    View
  3. Mike Zakowski (aka Mike the Baker) standing in front of his wood-fire oven at the Sonoma Valley Farmers' Market

    NEW! Walkin' and Talkin': Break Bread, Go On a Panoramic Hike

    What’s a world-traveling, medal-winning baker’s favorite local hike? Weekend Sherpa co-founder Brad Day caught up with Mike Zakowski (aka Mike the Baker) at Sonoma’s Friday farmers' market, where his wood-fired loaves draw loyal crowds. Between bites of fresh-baked bread, they talk baking, travel, and why Sonoma's Overlook Trail is one of his favorite quick, panoramic hikes.

    View

  4. Hidden Botanical Garden

    Forget a dozen roses. Give your love a botanical garden. Hidden on the western slope of Sonoma Valley’s Mayacamas Mountains, Sonoma Botanical Garden has one of the Bay Area’s best displays of Asian flora—and it’s a brilliant place for a quiet picnic and some calming contemplations.

    View

Trending Stories SoCal

View all Stories
  1. People on ice learning to curl at Hollywood Curling

    You Go, Curl!

    Hollywood Curling’s Learn to Curl classes make the perfect setting for newcomers. Take the ice, and friendly curling instructors will teach you the basics.

    View
  2. Sponsored

    Warm Up to Winter in Reno Tahoe

    2026 is just getting started, but there’s one place already rising to the top as the best for adventure and relaxation: Reno Tahoe. The awe—and ahhhs—begin as soon as you arrive. G

    View

  3. Fall for These Falls

    Chase waterfalls in Redding’s Whiskeytown National Recreation Area. This 42,000 acres of wilderness park is home to four waterfalls. Hike to the tallest, the three-tiered, 220-foot Whiskeytown Falls.

    View

  4. Oh Snow Nice

    Live in California long enough, and you’ll come to know the rite of passage called “going to the snow”–when we ditch our fair-weather cities and towns in search of winter weather. Sequoia & Kings Canyon National Parks deliver a winter wonderland worth a visit if there’s been a good dose of snow.

    View