On the peninsula south of San Francisco, Calif., lies a selection of
fabulous trails on 25 open space preserves. Comprising 50,000 acres of
near-urban greenbelt, the areas are maintained and promoted for public use by
the Midpeninsula Regional Open Space District (MROSD). I recently had the
opportunity to visit one short, spectacular trail in one of the preserves:
Anniversary Trail at Windy Hill.
Windy Hill is one of the 24 open-to-the-public preserves maintained by the
MROSD. There are 13 miles of trails within this 1,306-acre preserve. As the
name suggests, Windy Hill is a breezy location, ranging from grassy, open
hilltops, such as the area I hiked, to wooded gulches dipping down to the
A multi-use area, Windy Hill is open to hikers throughout, and to bikers,
equestrians, and leashed dogs in certain areas. Kite flying is allowed, and
hang gliding, paragliding, and soaring (radio-controlled gliding) are allowed
by permit. Windy Hill preserve spans a hillside in Portola Valley, stretching
from Skyline Boulevard on the west to Portola Road and Alpine Road on the east.
Vehicle parking and trailheads are available on both the east and west flanks
of the preserve.
An ideal hiking loop would be a combination of the Hamms Gulch Trail and
Razorback Ridge Trail, both of which climb from the valley floor to the hilltop,
linking via the Eagle Trail on the downhill (Alpine Road) side and the Lost
Trail on the uphill (Skyline Boulevard) side. This four-trail combination
totals 7.2 miles, but in order to reach one of several possible parking lots,
the total hike would be closer to 8 miles. This trail offers both hilltop
views, as I saw from the ridge top Anniversary Trail, and also hiking in the
forests of redwood, fir, and oak along the eastern flanks of the hillside.
This 0.7-mile loop trail is called Anniversary Trail because it was built in
celebration of several aspects of public hiking and nature preservation in this
area. The year of its construction was 1987, which was MROSD's 15th year and
the 5th year of public hiking on Windy Hill. It was also the 10th year of the
Peninsula Open Space Trust (POST), the organization who built the trail.
Anniversary Trail is accessed from Skyline Boulevard, either from a roadside
pullout at the north end of the loop (also the Spring Ridge Trail trailhead),
or a little farther south at a larger parking lot that includes restrooms and a
The trail is exposed, open, and virtually always breezy. There is little
elevation gain or loss, but since it's at the top of the ridge, views along the
backside are absolutely spectacular. All of the south San Francisco Bay Area
lies in front of you like a topographic map. The tower of Stanford University
lies immediately below you in wooded Palo Alto, the Dumbarton Bridge (Highway
84) is just to its north. A bit farther north, you can clearly see the San
Mateo Bridge (Highway 92), and casting your eyes quite a bit farther north, the
San Francisco-Oakland Bay Bridge is visible on all but the foggiest of days. To
the west of the Bay Bridge, the city of San Francisco can be seen.
There are two very short spurs along the backside (i.e., east side) of the
loop, if you are inclined to do a little climbing for more of a
"king-of-the-mountain" vista. Each is worthwhile in its way, but the
view of the Bay Area below really doesn't improve.
Native flora and fauna along the way may include poison oak (more likely
farther down the hillside toward the wooded areas), rattlesnakes (quite likely
on the exposed ridges in warm weather), and coyotes (I saw a large one toward
the south end of the loop, looking healthy and spry as a well-fed German
Shepherd). Mountain lion warnings have also been posted at trailheads in this
More About MROSD
What is the Midpeninsula Regional Open Space District? From a governmental
standpoint, it's a legal entity known as a "special district," as
defined by the State of California. More familiar types of special districts
include sewer districts, fire protection districts, and school districts.
open space district is a lesser-known type of district that "acquires and
preserves open space lands; protects and restores the natural environment; and
provides opportunities for ecologically sensitive public enjoyment." The
MROSD is funded through taxation, grants, and donations.
Like most of the trails and recreational areas within the MROSD, Anniversary
Trail and the other trails within the Windy Hill Open Space Preserve are open
from sunrise until one-half hour after sunset, with seasonal/weather-related
Sally O'Neal is a travel writer who makes her home in the Pacific
Northwest. She considers the San Francisco Bay Area and Tuscany, Italy, her
second homes, visiting each as often as possible. So many trails, so little
time! She writes weekly for Sportsmansguide.com.