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.
This is the entrance to the Betsy Crowder Trail which is a nice shortcut to the main Spring Ridge Trail. This trail is only open to Hikers and Horses (seasonal only)...so its a bit more private than the main trail.
The trail is very well traveled and is currently in great condition. You will pass Sausal Pond on the left which is full of birds, ducks and frogs. The Trail is a ways from the Pond, but you can still hear all the activity.
The Betsy Crowder trail will meet up with the Spring Ridge Trail and you will continue up Windy Hill to the summit on this very WIDE trail. The Spring Ridge Trail is open to Bikes and Horses and can get very "busy" during peak times. The trail starts out with a easy incline but at about half way you will notice the trail gets steep. Even Dogs have a tough time making it up at this point when its too hot.
The Views from this trail are great, you can see San Francisco, Mt. Diablo, San Jose, as well as the area towns of Portola Valley and Woodside.
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.
At this point, continue up the Anniversary Trail up to the true Summit (just 0.2 miles) . Here you get a 360 view of the Bay Area and can see the Pacific Ocean on a clear day.
The way back down is great with even more views and a very EASY walk down. There are a lot of dogs on this trail and unfortunately some dog owners are not cleaning up after their pets. But that was my only complaint. This is a great trail that is very well maintained and should be a "must do" hike if you live in the Bay Area.
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.
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.