The San Rafael-Olema Road, completed in the 1860s, ran along the base of Red Hill just as Red Hill Avenue and Sir Francis Drake Boulevard do today. In 1898, the dirt road passed a few roadside businesses and scattered houses; today, the road has four lanes, passes numerous businesses, including the Red Hill Shopping Center, and has lots and lots of traffic.
The zigzag road clearly visible today on the western slope of Red Hill was constructed about 1893 by Dr. Henry A. DuBois. DuBois, a pioneer San Rafael physician, developed the Mt. Tamalpais Cemetery on the other side of Red Hill in 1878. Unable to provide easy access to the cemetery from San Anselmo, he purchased a portion of the steep hillside and hired Chinese laborers to dig a road to the top and connect to his cemetery property. It was dubbed “DuBois’s Folly.” And a folly it was as the road was too steep for a horse and buggy to make it to the top and to the cemetery.
In 1916, two young San Anselmans made the trip to the top in their Ford. According to a San Anselmo Herald news story, it was the first vehicle to go to the top of the hill since Joseph Maghetti, who lived at the foot of Red Hill where Lanna Thai Restaurant is located, took a wagon to the top and brought down a load of wood 23 years earlier. The two adventurous travelers had to use a mattock to dig out in places so they could make some of the turns. The speedometer showed that it was 3/4 of a mile up the hill, but it took them 1-1/4 hours to reach the top.
In 1924, long after DuBois’s death, Arbor Road connected Sir Francisco Drake to the Mt. Tamalpais Cemetery. It was closed in the mid-1930s. Today, Shaw Drive follows that roadway part way.
The steep wedge-shaped parcel is today owned by the Town of San Anselmo. The climb to the top is difficult, but a new trail is being constructed. Those who do make it to the 464 foot summit are rewarded with fine views of the Ross Valley. They also stand at the demarcation point of three 1840s Mexican land grants – Rancho Canada de Herrera, Rancho Punta de Quintin and Rancho San Pedro, Santa Margarita, and Las Gallinas.