Woodside: The Anatomy of a Boom Town

John DeOliviera, Senior Buyer Specialist – March 16, 2017

Woodside is located in the heart of Silicon Valley and is home to many chief executive officers, venture capitalists, and founders of the area’s many high-tech companies. But before evolving into one of the most sought-after addresses in the Valley, Woodside witnessed a long, transformative history which helps to enhance its present-day appeal. Initially, the area was the naturally gorgeous habitat of a people called the Ohlone tribe. This native people occupied the lush, lovely terrain, enjoying the mild climate, creeks, and forests which produced an abundant supply of food and water. In 1769, a group of Spanish explorers led by Gaspar de Portola even set up camp in an area near Woodside. Without question, Woodside enjoys a historic setting of wondrous beauty. In contrast to its bucolic roots, Woodside also formed the scene of the greatest activity in the Bayshore area of San Mateo County. It attracted many explorers and settlers and is said to be the oldest English-speaking settlement in the southern part of the Peninsula. The first English-speaking settlers arrived in the early 19th century to log the rich forests of redwoods. Dotted throughout Woodside were the mills which supplied San Francisco with its first loads of lumber; this lumber, in turn, gave the county seat of San Mateo its name of Redwood City.

Charles Brown constructed the first sawmill in San Mateo County on his Mountain Home Ranch. His adobe house, erected in 1839, still stands today. By the middle of the 19th century, the Woodside area housed a dozen mills producing building materials for booming San Francisco. In 1845, a gentleman named Dennis Martin came to the area in the first wagon party over the Truckee Pass. He bought 1,000 acres of land from John Coppinger, and consequently put up a house and two sawmills, planted orchards, and built St. Denis Chapel, which for years was the only place of worship between San Francisco and Santa Clara. In 1849, during the California Gold Rush, 20-year-old Mathias Alfred Parkhurst purchased 127 acres of timberland and gave it the enduring name of Woodside. His friend, Dr. Robert Orville Tripp, a dentist, arrived in Woodside, and he and Dennis Martin went into partnership in the lumber business. The lumber was cut and dragged by oxen teams through the redwood forests to the shores of the bay, then floated by raft to San Francisco. The corridor they created to the shore now forms the heart of Redwood City.

As the lower hills were timbered out, the mills were moved up the canyons and over the hills. Meanwhile, Dr. Tripp and Mr. Parkhurst opened the Woodside Store on Kings Mountain Road, which is now preserved as a San Mateo County museum. Dr. Tripp continued his dental practice and in 1851 was elected as supervisor of San Mateo County, a position he kept until his death in 1909. Many other folks were attracted to the beautiful Valley and, by 1852, a regular stagecoach service to San Francisco had been established. Woodside citizen John Greer gave land for the first schoolhouse and, by the end of 1859, there were 112 pupils. The Library Association was one of the first of its kind to be established in all of California. In the 1850s, a town known as Searsville sprung up because of the many sawmills and lumbering businesses in the area. In 1853, August Eikerenkrotter built a hotel to house teamsters and other passersby. The following year, John W. Sears arrived and built a home and another hotel in the new town. The town took on his name as Searsville and blossomed in the 1850s and 1860s, eventually boasting a church, a school, several saloons, and a blacksmith shop.

Over time, the lumbering business moved across Skyline, and the area slowly transformed into a small farm community. When the area was bought out by Spring Valley Water Company, it began to build a dam. Eventually, the buildings of this fledgling town were disassembled and the community was flooded out. The loss of population, along with the decline in logging, finished the town of Searsville. Many residents today are not even aware of the existence of this once-bustling village. Gradually, the character of the Valley changed. Sawmills were replaced by farms, small cattle ranches, and vineyards. In the 1880s, prosperous San Franciscan families began to establish country estates in Woodside. The Pioneer Hotel was built in 1882, and current residents can still glimpse the hotel’s original façade. Independence Hall was built in 1884, but was moved from location to location until it was finally relocated next to Town Hall in 1991. It is still used today for local meetings and events. After WWII, the growth of San Mateo County was rapid, and construction further altered the mid- Peninsula landscape. In the 1950s, Woodside began to feel the effects of the growing population. For fear of urbanization, Woodsiders voted to incorporate their community, which occurred on November 16, 1956. This brought management, road maintenance, planning, and zoning under local control, which continue to be primary functions and responsibilities of the town today.

Recreational activities are a large part of Woodside’s culture. Numerous residents keep horses—some homes are even considered farms—and the town government maintains a network of horse trails. Woodside is also popular amongst avid cyclists, which flock in large numbers on the weekends to popular cycling routes like Old La Honda Road, Kings Mountain Road, Canada Road, Skyline, and Highway 84. Famous Skeggs Point along Skyline Boulevard is a magnet for mountain bikers. Of course, given the area’s extensive natural beauty, it is not surprising Woodside is also home to a number of open space preserves, including Purisima Open Space, where both horseback riding and cycling are allowed.

Woodside is proud of its humble beginnings as a lumber town and, today, is among the wealthiest small towns in the United States. It now boasts intentionally small business districts which include a few restaurants, a saloon, a Post Office, and grocery, hardware, and garden stores. There are few towns in America that can match Woodside’s natural beauty, rich history, near-perfect weather, and peaceful rural life within such close proximity of a world-class urban setting.