Hillsborough is a town of rare affluence, number five on Bloomberg Businessweek’s 2009 list of “Wealthiest Towns in America.” It’s a unique place, with no shops,
no restaurants, and no commercial entities of any kind within its borders. Its citizens live on half-acre minimum lots, many behind gates and rows of tall trees.

Though it’s arguably the most exclusive community in San Mateo County, amazingly Hillsborough today cannot compare to the Hillsborough of its origins, a place of almost unimaginable wealth that sprung up on part of the former Rancho San Mateo in the mid-to late-19th century; that Hillsborough was something else entirely. 

It began before California had even become a state, when transplanted New Englander-turned San Francisco business titan William Davis Merry Howard and a business partner paid $25,000 in 1848 to purchase the 6,500-acre Rancho from Cayetano Arenas. In 1850, Davis bought out his partner, becoming the sole owner
of the ranch. All told, Howard’s land stretched from

San Francisco Bay to the western hills, covering almost all of present-day Hillsborough, much of present-day Burlingame and San Mateo. On it he built a country home called “El Cerrito.”

Unfortunately, Howard didn’t have much time to enjoy his country home. He died in 1856 at the age of 36, leaving much of his estate to his wife, Agnes, who then married his younger brother, George. The newlyweds began spending more time at El Cerrito, adapting the property to suit their needs. Like other wealthy San Franciscans, they found access to the area greatly improved in 1983, when regular train service between San Francisco and the Peninsula became a reality.

The early history of Hillsborough is dominated by only a few prominent families, many of whom intermarried— the Howards, the Crockers, the Poetts, the Redingtons, and finally the generation that created Hillsborough, the town: the Newhalls, the Tobins, Carolans, the Clarks, the Grants and Francis Newlands, not a Hillsborough resident but the son-in-law of William Sharon and architect of the plan that became the Burlingame Country Club and ultimately, the town of Hillsborough.

Famed Golden Gate Park landscape architect John McLaren left his mark on the Hillsborough countryside. 

George and Agnes Howard created a template for all of them, “(setting) the pattern for genteel living down on the Peninsula,” according to historian Frank Stranger. They welcomed family and friends into El Cerrito and hired legendary Golden Gate Park landscape architect John McLaren to plant hundreds of eucalyptus trees on their property.

In 1893, Francis Newlands happened upon an idea to convert some of his family’s dairy farm acreage (used
to provide milk for the family’s prized possession,San Francisco’s Palace Hotel) into for-sale real estate. He hired architect A. Page Brown to design five grand “cottages” and marketed them to wealthy San Franciscans. When that alone could not attract buyers (for a time, the cottages were used as adjunct lodging for the Palace Hotel), Newlands, along with a few other prominent second-generation locals, decided to create the Burlingame Country Club to sweeten the deal. Among the founders of the first American country club located west of the Mississippi River were William H. Howard, son of Agnes and William Davis Merry Howard. 

Hillsborough’s founding families owned massive acreage on which they built great 96-room mansions. The most fabulous of these was Carolands, the 96-room estate of Frank Carolan and his wife, railroad heiress Harriet Pullman Carolan. Carolands’ 554 acres were subdivided in the 1940s and 1950s by Moseley, who created the Carolands housing subdivision, naming the streets after members of his family.

On that day, all of Hillsborough came to St. Matthew’s Military School to vote for incorporation. Townspeople, fearing annexation by neighboring Burlingame (and the unwanted infrastructure upgrade that would come with it) voted 60 to 1 in favor of incorporation, which came— officially—on May 5, 1910. Pointedly, the new town’s laws included one forbidding sidewalks from all properties.

Eventually, many early Hillsborough mansions met similar fates as that which befell Carolands. Most
lost the majority of their land when later owners, hamstrung when servants left to fight in World War II, making staffing the large homes difficult and/or extremely expensive, sold to developers. Some were razed completely. Today, only a handful of the old estates remain standing. 

World War II marked a turning point for the era of massive Hillsboroughs estates. 

Two mansions, “Skyfarm” (a gift from William H. Crocker to his sister-in-law on her wedding day) and
C. Templeton Crocker’s “Upland” eventually became the centerpieces of two independent schools, Nueva and Crystal Springs Upland, respectively. The Crockers donated another family home, the “New Place,” to the Burlingame Country Club in the 1950s.

By then, Hillsborough’s era of the great estates was over. In its place came a period of accessibility. The new subdivisions catered to Hillsborough’s new professional class—doctors, dentists, lawyers, brokers. This was a period of great growth for the town, which responded by adding two new elementary schools, North Hillsborough School (1950) and West Hillsborough School (1954), and eventually Crocker Middle School (1959). Many of the estate homes that survived sat, like Carolands, on much smaller lots, surrounded by newer subdivision homes. Some, like the Tobin Clark Estate, George Cameron’s “Rosecourt” and George Newhall’s “Newmar,” which was renamed “La Dolphine” when later owned by Dorothy Spreckels, still function as private homes today. Carolands, after years of neglect, was purchased in 1998 by Charles and Ann Johnson, who completely restored it to a level similar to its former glory. 

Though it will never return to the days of 500-acre estates, Hillsborough’s latest chapter echoes its first in that it has again become a secluded getaway for many of the era’s most successful residents. This time, instead of railroad titans, it’s tech titans; unchanged, though, is the fact that for a century Hillsborough has enjoyed the favor of the Bay Area’s wealthiest few.