This popular hike starts at the Parking Lot off Portola Road in Portola Valley. The lot was empty when I arrived at 8am, but was PACKED FULL when I returned at 10:30am. My suggestion is to do this hike early in the morning, during the Spring/Summer the area can get a bit warm, but the mornings are usually cool and clear. The area is open at Dawn and closes after Sunset.
At mid-point you might thing about turning back, since the trail gets quite steep -- even though its very wide and easy to walk on. But keep going up! You will pass through a zig-zag part and before you know it you will be at one of the Skyline Entrances.
My route: Start on Parking Lot off Portola Road (NOT off Hwy 35). Take the Betsy Crowder Trail to the Spring Ridge Trail then on to Anniversary Trail to the Summit.
More Photos
Basics:
Area - Midpeninsula Regional Open Space District - Windy Hill in Portola Valley
Trail - Betsy Crowder Trail/Spring Ridge/Anniversary Trail (Trail Map)
Length - 5.2 miles roundtrip - Moderate Hike (some steep parts)
Trail - Up and Back-style, dirt trail/dirt road, some stops along the way. Very well marked and maintained. No roads to cross.
Dogs - Yes - Lots!
Bikes - Yes, on most main trails
View - Tons, bring a camera
Getting There - Google Map Take 280 to Alpine Road Exit, head West toward Portola Valley. Turn Right on Portola Road (first stop sign). The Parking Lot has a sign and will be on the Left after the Sequoias Retirement Community.
Fee- None, free parking
Weather - If you can see Fog, bring a jacket -- otherwise you might want to pack a sweater for cool mornings. I found it really only "windy" at the Summit.
Other Trails - there are other trails within this park. Trail maps and info available at the Parking Lot.