Bay Area road bikers know the Loop as an 11 ½ mile oval-shaped course, curving through Portola Valley. While the Loop is generally an easy-going, stop-free cruise, the real challenges are found in the side-loops, many of which are off Alpine Road, the first Loop segment clockwise from the Stanford Golf Course.
Ahead after crossing San Francisquito Creek and going due south under I-280 over the next mile-and-a-half, are three residential subdivisions on the right. All three entering roads—La Cuesta Drive, Westridge Drive and Golden Oak Drive—are about three-miles long, winding past homes and having grades from 14% to 16% with crests several hundred feet above Alpine. Steep up mean steep down with care to be taken on the quiet, narrow roads where bicyclists aren't usually seen. Two of the three roads return to Alpine with Westridge taking you to Portola Road.
Located where Arastradero Road crosses Los Trancos Creek on the left is The Alpine Inn, or “Formerly Rossotti's” as is painted on the false front. Built as a brandy-guzzling cardhouse in the 1850s, grizzly bear-bull fights on the back lot have since been replaced with old wooden tables on which to set beers and burgers. The Arastradero creek crossing was a short cut to the village of San Jose and nearby Mission Santa Clara, where oxen hauled the cut timber, with arrastrar meaning “to drag.” Its backstory is as rough as it looks. The tale goes that original Mexican tavern owner surrendered his deed in 1868 to an American as a gambling debt payoff. Twenty-years later, that owner and horse were killed when his buggy crossed in front of a train near Redwood City. For the next fifty years, his widow leased the place to many owners, getting through prohibition with the accompanying tales of bootlegging and prostitution. When the widow died, Enrico Rossotti held the property from the 40's to mid-50's, with the nickname Zott's implanted in the memories of carousing Stanford students, demure Portola Valley horseriders, leather-jacketed motorcyclists, lunch-breaking laborers and venture capitalists, as well as weekend bicyclists getting a cold one near ride's end.
Up ahead on the left, well past the scenic soccer field and busy tennis club, Los Trancos Road continues to follow the creek of the same name, which means “big steps” in Spanish, appropriately named for the climbs upwards, especially the first big hump into Los Trancos Woods, a cluster of homes dating back to the '20s. From Alpine Road to the top of Vista Verde Way is 4 miles and 1300 feet of climbing, averaging 9% for the last couple miles. It's a worthy climb with all the feel of a private road.
Had you stayed on Alpine, you would have passed Portola Valley Garage on the right and a small roadside marker indicating the garage was the homesite of Maximo Martinez, the original owner of the area's Mexican land grant, called Rancho Corte del Madera, or “ranch where timber is cut.” Ahead on the right is little-used Hillbrook, briefly reaching 18%. If in the mood to dally, beyond the path closed to cars are tranquil Arrowhead Meadows and streets such as Cherokee, Shawnee Pass and finally Iroquois, where Martinez built his second home, safe from the dust and noise of Alpine. In 1891, 23-year-old William O'Brien Macdonough, who inherited his wealth from the Comstock Lode fortune, bought the former Martinez estate, renamed it Menlo Stock Farm and began developing race horses in competition with 67-year-old Leland Stanford, who was busy transforming part of his Palo Alto Stock Farm into a university named for his deceased son. In 1893, Macdonough purchased the undefeated and retired Ormonde, the most famous horse in the world, for $150,000. His nearby stock farm competitor, Stanford, however died in June. A year later, Ormonde died but his foal Ormondale was born and Macdonough renamed his ranch in the colt's honor. Though not the winner that his sire was, Ormondale was a champion stud, with one offspring being the 1941 Triple Crown winner Whirlaway. Ormondale Elementary School, built in 1961, stands quietly, except during recess, where Macdonough's race track once was. Georgia Lane, part dirt, takes you back out to Portola Road or you keep exploring, maybe finding Possum out to Hidden Valley to Portola instead.
In 1868, Alpine Road was granted as a franchise toll road by the county supervisors to the Menlo Park and Santa Cruz Turnpike Corporation. However, within a few years, residents began complaining that the poorly maintained road had become impassible in winter. In 1874, the company forfeited the road to the county. At that time, the four-mile road had only extended a little beyond the Portola Corners stop sign, ending opposite Willowbrook at the bottom of a former Native American footpath to the coast. The path was used by Mission Dolores soldiers chasing after a renegade from the missions named Pomponio, who hid out in Devil's Canyon, named in his honor, near the Alpine-Skyline crest. What became known as the Old Spanish Trail ascends Coal Mine Ridge, named after what was prematurely thought to be a valuable discovery. Users of the toll road that stopped at the base of the ridge discovered that easily getting all the way to Santa Cruz from there was a fantasy of its own.
The Old Spanish Trail was used to bring cattle from a coastal ranch to settlements near what became Palo Alto and Robert Tripp's supplies to his Pescadero store from his Woodside store, using the ridge that avoided the fallen trees and landslides of the creek below. With machinery, the county later extended Alpine Road alongside the unstable and narrow canyon of Corte Madera Creek, aligned with the San Andreas Fault. Never paved, the snaking, upper section is well used by mountain bikers. Road bikers reaching pavements end two-miles up from Willowbrook can turn left on Joaquin Road, named for the bandit Joaquin Murrieta, who mostly worked the gold rush foothills but reportedly had safe houses scattered locally amongst his sympathizers. The short but steep climb connects with the paved section of Old Spanish Trail, from which you can carefully twist your way through Los Trancos Woods back to Alpine.
Back at Portola Corners, the Loop turns right as Portola Road, later becoming Sand Hill Road, going over I-280 and through several stop-lighted intersections before reaching at Santa Cruz Avenue, which name retains that of the former toll road. Alpine Road, gateway to Portola Valley's early history and residential slide loops, is just around the turn to the right.
Published Cycle California, July 2014, Vol. 20, #6