An alternate route is to do the simple out and back on the Razorback Ridge trail, but I had time and wanted to do a "loop"
Trail Route (loop) : Hamms Gulch Trail -> Lost Trail -> Razorback Ridge Trail -> Eagle Trail/Alpine Road
Alternate Route (Out and back) : Eagle Trail/Alpine Road -> Razorback Ridge Trail and back
Near the summit, you will reach the end of the Hamms Gulch trail. At this point you continue south (left) on the Lost Trail.
Since you are at the summit of the mountain, the Lost Trail mostly in the open with high brush on either side. There are some shady areas, but there is lots of open sunny path.
The Lost Trail is fairly narrow and is mostly a single track trail. It is very well maintained and provides a great experience on the top of the ridge.
At one point, you will pass a small water trough for horse. This water comes from a nearby spring in the mountain.
After passing the water trough, you will soon reach the intersection with the Razorback trail. Here you continue downhill to the left.
The razorback ridge trail is fairly enjoyable, and provides mostly shade all the way down to Alpine road. However, this trail is full of tight switchbacks. It should be called "switchback" ridge trail, but Razorback sounds better.
At some points the sides along the trail are fairly steep, but the trail is very well maintained. no bikes are allowed on this trail -- but it is popular with runners/joggers.
The Razorback Ridge Trail provides a couple view points along the way -- more than the Hamms Gulch trail provides.
Some guide books suggest this routing as one of the "Best Hikes in the Bay Area" -- but this seems odd, since you completely miss the fantastic views from Windy Hill back to Bay Area. I would highly recommend this hike, if you want to experience one of the REAL Best Hikes in the Bay Area.
The Razorback Ridge trail ends on a private drive near Alpine Road.
One the way back to the parking lot, you can either walk down Alpine Road (paved road) or take Eagle Trail side trails.
The Eagle Trails are ok and run along the Corte Madera Creek. They are single track trails.
The Eagle Trail will end at this road, you should turn right to get back to Alpine Road. If you turn left, you can connect back with the Hamms Gulch trail.
This was an enjoyable hike, but if you want to avoid switchbacks and have a really nice view you should take the Hamms Gulch - Windy Hill loop instead.
More photos of Windy Hill
Area - Midpeninsula Regional Open Space District - Windy Hill in Portola Valley
Trails - Hamms Gulch Trail/Lost Trail/Razorback Trail/Eagle Trail (Trail Map)
Length - 8.2 miles roundtrip - Easy Hike (uphill, but easy)
Trail - Loop, dirt trail, limited stops along the way. Well marked and maintained, dry starting in May.
Dogs - Some (not allowed on Razorback Ridge Trail)
Bikes - Not allowed on this hike, allowed on other trails
View - Just a few
Getting There - Google Map Take 280 to Alpine Road Exit, head West toward Portola Valley. The parking lot is before Willowbrook Road.
Fee- None, free parking
Weather - Lots of Shade, can be wet at the top if very foggy during the summer.
Other Trails - there are other trails nearby including the Windy Hill Loop and Portola Ranch Trails