Windy Hill Open Space Preserve, Portola Valley, CA

Just off I-280 on Alpine road, Windy Hill provides a formidable hike, with an 1100+ foot elevation gain over 2.5 miles (>5-mile round trip). Start at the trail head, then go 0.7 miles along Meadow Trail before turning left when you hit Spring Ridge Trail. Continue for 1.6 miles up the steep rolling hillside paths, then take Anniversary Trail 0.2 miles to the summit. You'll enjoy excellent views of the bay. Be sure to bring water and sunscreen. For those who want to skip the uphill struggle, park at Skyline Boulevard and take the 0.7-mile Anniversary Trail loop.

Trail: Spring Ridge Trail + Meadow Trail, 5.4 miles, 1100ft elev gain
Difficulty: >Moderate (elevation change, steepness, exposure to sun)