The San Anselmo neighborhood most of us know as “Sleepy Hollow” was once part of the Mexican Land Grant, Rancho Canada de Herrera, that was first given to Presidio soldier, Domingo Sais in 1839. In 1853, the land passed to his son Pedro who leased the area to Harvey ‘Butterfield’ who built a home there and raised cattle for milk. As the ranch was a few miles up a dirt road from the main east-west trail, wagon drivers and riders referred it to as “The road to the old Butterfield Place,” which eventually was shortened to “Butterfield Road.” In 1863, Pedro Sais sold the land to investors who planned to build a luxury hotel at the end of Butterfield Road. However, the property was foreclosed upon and the partners never realized their dreams though many of the large poplar and eucalyptus trees they planted still line the road today.
Anson P. Hotaling, the wealthy owner of Hotaling Liquors in San Francisco, bought the property in 1889 and leased some of the land to local dairyman, Frank Denez. In 1890, Anson’s youngest son Richard, a member of the exclusive Bohemian Club and an amateur actor, built a large and elegant mansion at the end of the road that featured a grand staircase of imported Spanish cedar and an immense living room with a raised platform and theatrical balcony for the staging of plays. The foundation of the mansion is still visible at the entrance to present-day San Domenico School. Richard also took over operation of the dairy and imported 200 Holstein cattle from Holland and named the area Sleepy Hollow after Washington Irving’s literary masterpiece. Richard eventually sold the herd and 1600 acres to his friend, Sigmund Herzog of San Rafael, a successful businessman, property owner and banker. In 1910, Herzog established the first certified milk dairy in the United States that featured mechanical milking machines and a rigorous protocol of washing and cleaning the cattle, barns and equipment.
After a long, bitter court battle in the 1920s between Richard and his family, the land was sold to a Chicago Syndicate that hoped to build two golf courses and use the mansion as the clubhouse. Sigmund Herzog moved his “Sleepy Hollow Dairy” to Petaluma where it still survives today. The stock market crash of 1929 put an end to the golf course project and the land lay fallow for a few years. Lang Realty bought a portion of the land and would eventually build homes in the area. In 1935, investors George Keanel and H.A. Willard bought the mansion and surrounding land and built an 8,000-yard championship golf course converting the mansion into the popular Sleepy Hollow Clubhouse and Restaurant.
With the onset of World War II, water was diverted from the course to Hamilton Field and the Sleepy Hollow Golf Club passed into memory. For a time, the U.S. Army occupied part of the valley building a secret ammunition storage depot and installing two antiaircraft batteries. After the war, hundreds of homes were built along streets that were named after characters and locations in Irving’s The Legend of Sleepy Hollow.
In 1957, the abandoned Hotaling Mansion was destroyed in a mysterious fire that was blamed on arsonists. A year later, the Dominican Sisters of San Rafael purchased the old Hotaling estate land and construction began on San Domenico School in the summer of 1964. By the fall of 1966 students began attending the school that lay at the end of “…the road to the old Butterfield Place” in “Sleepy Hollow.”