In 1769, a group of explorers led by Gaspar de Portolá searching for San Francisco Bay, camped near Woodside. In 1822, Mexico gained independence from Spain, and the Spanish Land Grants passed into private hands.

The Woodside area is distinguished for having been the home of some of the first English-speaking settlers on the San Francisco Peninsula. In the 1830's William Smith (Bill the Sawyer), a fur trader from Oregon, made his home in Woodside, as did John Cooper and James Pease. Charles Brown built the first sawmill on his Mountain Home Ranch. His adobe house was built in 1839 and stands today.

The Rancho Cañada de Raymundo was granted to John Coppinger by his good friend Juan Alvarado, the Governor of Mexico. Coppinger, a former lieutenant in the British navy, married Luisa Soto, the daughter of a Spanish ranchero. In 1841, Coppinger built the first wooden house in Woodside at the corner of Kings Mountain and Woodside Roads.

Dennis Martin, who came in the first wagon party over the Truckee pass in 1845, bought one thousand acres of land from John Coppinger. He put up a house and two sawmills, planted orchards, and built St. Dennis Chapel, which for years was the only place of worship between San Francisco and Santa Clara.

In 1849, Dr. Robert Orville Tripp, a dentist, arrived in Woodside to recuperate from an illness, and stayed to establish a business and a home. He and his friend, M.A. Parkhurst went into the lumber business in partnership with some San Francisco builders. They opened a direct road from the redwood forests to the head of the tidewater in Redwood Creek -- now the heart of Redwood City. The lumber was dragged by oxen teams over this road and floated by raft to San Francisco. By 1855, there were at least eight sawmills and one shingle mill in Woodside. As the lower hills were timbered out, the mills were moved up the canyons and over the hills.

Meanwhile, Dr. Tripp and Parkhurst had opened the Woodside Store on King's Mountain Road, which is now preserved as a San Mateo County museum. He continued his practice of dentistry, and in 1851 was elected a supervisor of San Mateo County. Until his death in 1909, Dr. Tripp operated the store with a post office serving customers from as far away as San Mateo and Half Moon Bay.

More people were attracted to this beautiful valley, and by 1852 there was a regular stage coach service to San Francisco. John Greer, who married John Coppinger's widow, gave land for the first schoolhouse. By 1859 there were 112 pupils enrolled. Another school, the West Union School, had 72 pupils. The Library Association was one of the first of its kind to be established in California. Another result of this boom was the number of saloons which multiplied on Whiskey Hill Road. To combat these, John Greer and Dr. Tripp, built the Dell Temperance Hall in 1856, which served as a social center for the community.

Gradually, the character of the valley changed. The sawmills were replaced by farms, small cattle ranches, and vineyards. In the 1880's prosperous San Francisco families began to establish country estates in Woodside. The First Congregational Church of Redwood City built a small church in 1893. It now serves as the chapel for the Woodside Village Church. The Pioneer Hotel was built in 1882, and the original facade still stands. Independence Hall, built in 1884, was originally located on what are now the elementary school's tennis courts. It was moved in 1894 to Albion Avenue, but closed in 1921 due to "rowdiness" during prohibition. In 1944 it was rededicated as Scout Hall. However, in 1972 the land on which it stood was sold, and it was moved back to the elementary school. It was moved, finally, in 1991, completely restored, and now stands next to Town Hall, at 2955 Woodside Road. It is used for Town meetings and events.

After World War II, the growth of San Mateo County was rapid, and construction altered the mid-peninsula landscape. In the 1950's, Woodside began to feel the effects of San Mateo's growing population as 555 new houses were constructed. After several large parcels of land had been sold to developers, some of the residents anticipated. that continued unrestricted growth would result in the transformation of Woodside from a rural residential community into a less attractive, more urbanized one. They raised the issue of increasing the degree of local control over -public activities. By a close vote of 646 to 574 on October 20, 1956, Woodsiders voted to incorporate. Incorporation on November 16, 1956, brought road maintenance, management, planning and zoning under local control and budget. These functions remain the primary responsibilities of the Town.