Windy Hill is a popular and very enjoyable preserve that stretches from Portola Valley, at the base of the Santa Cruz Mountains, to Skyline Boulevard, at the crest. In between is some of the most attractive woodland on the bay side of the ridge, including a few pretty impressive old-growth Douglas-Fir trees, plus the distinctively bald ridge that rises up to Windy Hill itself.
Windy Hill has a relatively low elevation, so its views of the Bay Area aren't as spectacular as, say, the view from nearby Black Mountain Trail in Rancho San Antonio County Park, but the views are still pretty nice and, combined with the exceptionally nice trails, make a hike that's hard to beat.
In fact, Windy Hill's low elevation is part of what makes the park so attractive. Since it's located below a saddle in Skyline Ridge, summertime fog often spills over the ridge into the park, resulting in forests that are much more lush than those just a few miles to the south. If at the beginning of this hike you see a bank of fog spilling over Skyline Ridge and down the hills above Portola Valley, Skyline Ridge is going to be cold, damp, and windy, even if it's warm and sunny at the bottom. Temperatures can drop into the 50s even in July.
Another reason Windy Hill is so enjoyable is that most of its trails are singletrack. Most other local open space preserves are dominated by fire roads, which tend to isolate you from the environment and aren't as enjoyable to hike. Interestingly, though, the most popular trails in the park seem to be the fire roads.
The 10-mile hike described here is by far the most enjoyable of the many hikes that climb the eastern (bay) side of the Santa Cruz Mountains to Skyline Ridge. There are a nice variety of environments: the hike begins in the woods, then breaks out into open grassland with sweeping scenic vistas. Even though the park is just a few minutes' drive from Highway 280, it feels remarkably isolated and there's very little traffic noise.
Windy Hill is one of the few Bay Area preserves where dogs are allowed on the trails.
Start at the Windy Hill parking lot in Portola Valley. A short access trail leaves the parking lot and leads to a dirt road. Turn left onto the road, which passes by a small pond mostly hidden by vegetation, then begins a gentle climb through attractive oak woods. The road is surrounded by shrubs so there's not much to see, although at one point there's an old cattle chute to your left.
The dirt road ends at a private, gravel driveway. Cross the driveway to where a driveway bypass trail begins on the other side. Immediately turn right, heading uphill toward Hamm's Gulch. After just a few yards there's another intersection, this one with the Meadow Trail, which heads uphill to the right. Stay on the left-hand trail, which slopes downhill into a little wooded ravine.
After stepping across a creek, you'll come a T intersection with the Hamm's Gulch Trail. To the right, the trail climbs uphill to Skyline Boulevard; to the left, it descends. Turning right onto the Hamms Gulch Trail would produce a shortened loop of about 7 miles that's otherwise very similar to the Razorback Ridge route. Personally, I prefer the longer Razorback Ridge route because it includes a lot more of the very attractive woodland along Skyline Ridge.
To take this longer route, left onto the Hamm's Gulch Trail. The trail descends and soon ends at a paved private driveway. Turn left onto the driveway, cross an auto bridge, then turn right onto the Eagle Trail. This trail runs just below Alpine Road, eventually climbing up and joining the road. The trail then begins again before rejoining the road a second time.
Just after the trail rejoins the road, look for a private driveway with a park trail sign. The driveway crosses a creek, passes a house, and then begins to ascend. The well-marked trail begins to your right.
The Razorback Ridge Trail switchbacks up a steep, densely-wooded hillside above a ravine. It's a fairly easy climb. The woods are lush and attractive. Surprisingly, there's no traffic noise or other sign of civilization. There's a lot of poison oak along this stretch of trail.
At first the trail mostly climbs on the south side of the ridge, but about halfway up it crosses over to the north side. At this point the woods become brighter and more open, and there are also a few glimpses of the Bay Area off to the right.
The woods become increasingly lush as the trail approaches Skyline Ridge. After an intersection with a spur trail to Skyline Boulevard, the trail levels out and meanders through attractive woods. This part of the trail used to be a road but it's narrowed so much that it's hard to tell. The trail parallels Skyline Boulevard but is far enough away so that traffic noise is rarely heard.
The trail breaks out into open grassland, ascends to cross a dirt road, then re-enters the woods. At the intersection with the Hamm's Gulch Trail are some particularly impressive moss-encrested, old-growth Douglas-Fir trees. This area gets a lot of fog and the ground can be damp even in summer. Shortly afterward, the trail breaks out again into open grassland, this time for good.
Turn right onto the Anniversary Trail, which climbs up to Windy Hill, offering the best views of the hike. Two short side trails to your left lead up to separate knolls; skip the first, and take the second, which leads to the higher of the two peaks. There's a nice view here, not only of the bay, but of the hills to the west as well.
Continue on the Anniversary Trail as it descends, then turn right onto the Spring Ridge Trail. This dirt road is the most popular trail in the park, with hikers and mountain bikers puffing their way up to Windy Hill. It's steeper than the park's two wooded trails. The views of the Bay Area aren't quite as spectacular as the view from the top of Windy Hill, but there are some nice views of the richly forested ridges that you've just hiked over.
The trail descends into oak woodland. Turn left onto the Betsy Crowder Trail, which leads through a very pretty forest that's typical of the woods in Portola Valley, making a nice finish to the hike.
© 2010, 2016 David Baselt