After the United States acquired California from Mexico in 1848, a rush of new settlers from the east coast and Europe journeyed west to seek their fortunes in gold and start a new life.

One of the early pioneers, and probably the original Silicon Valley entrepreneur was Dr. R.O. Tripp, a native from Massachusetts, who arrived in 1849 to recover from an illness. He gave the small settlement on the hillsides of the Santa Cruz Mountains the name Woodside.

By 1852, a daily stagecoach service route was established between Woodside and San Francisco attracting many new settlers down to the emerging lumber industry in the Santa Cruz Mountains. The lumber was used to build San Francisco before and after the Great 1906 earthquake.

The ever-increasing number of lumberman and new immigrants from Europe to the area gave Dr. Tripp and his partners an opportunity to open the area's first general merchandise and supply store in 1854. The Woodside Store was the center of the community social activities until the 1880's when other commercial businesses began to open in town, and in the growing neighboring village of Redwood City by the bay. In 1893, the Neuman Brothers opened their first store.

Dr. Tripp's Woodside Store was the area's first "strip-mall" that included a bank with an armored safe, a dentist office where he extracted a tooth for $4 compared to $16 in San Francisco. He also added a circulating library with 589 titles and a saloon.

Tripp also produced wine grown back of the store on a five-acre vineyard. He grew Burgundy, Grey Riesling, and Muscat grapes bottled and labeled under the "San Mateo County Pioneer Brand," and dispensed over the counter alongside E.H. Rixford's La Questa Cabernet at his Woodside store.