The story of Woodside, California, is deeply intertwined with the spirit of the Old West, a history perhaps best savored within the walls of the Pioneer Saloon Woodside. While the name “Whiskey Hill” might evoke images of numerous rambunctious settlements across the Northern Mines, it’s Woodside in San Mateo County that proudly carries this moniker’s legacy, largely thanks to its enduring landmark, the Pioneer Saloon.
In the late 19th century, the area now known as Woodside was a hub of the burgeoning lumber industry. Fifteen sawmills operated within a five-mile radius of Tripp’s Woodside Store. This store, run by Doc Tripp, became a vital center for over a thousand lumberjacks, providing everything from dental care and mail to essential supplies and, yes, whiskey. Tripp’s Woodside Store, located at the corner of Kings Mountain and Tripp Roads, remained a cornerstone until Doc Tripp’s passing in 1909 and is currently preserved by the San Mateo County Parks and Recreation Division.
As San Mateo County’s wood industry flourished, serving San Francisco and Alviso, the commercial heart shifted eastward from Tripp’s quaint store. This new center, drawing teamsters hauling lumber to Redwood City Embarcadero, became known as Whiskey Hill. The name was earned honestly, thanks to the presence of three bustling saloons and two hotels, including one managed by Peter Hanson. These establishments, along with a blacksmith shop, sprang up to meet the needs of travelers and workers at this busy crossroads.
Whiskey Hill served as a crucial stop for teamsters transporting milled lumber from local mills to Redwood City. After navigating the initial two to four miles laden with heavy wagon-loads, teamsters would pause at Whiskey Hill. This provided a much-needed opportunity to refresh and prepare for the subsequent downhill journey of six or seven miles to the Redwood Embarcadero, or southward towards Santa Clara and San Jose.
Today, Whiskey Hill thrives as “Downtown Woodside,” a vibrant area where history and modern life converge. At its heart, the Pioneer Saloon continues to operate, dispensing its own brand of “spirituous elixir,” a living testament to the area’s colorful past. Alongside the Pioneer Saloon, Woodside Town Center and Independence Hall (dating back to 1886) contribute to the area’s flourishing commercial and community life at this historically significant intersection.
While Woodside embraces its Whiskey Hill heritage, it’s worth noting other locations also briefly carried similar nicknames. Searsville, another lumber camp in the region, now submerged under Searsville Lake on Stanford lands, also played a role in the area’s development. Further north, “Whiskey Gulch” became a local term for the commercial area of University Avenue near Palo Alto, a nod to the saloons that thrived just outside Jane Stanford’s prohibition zone around Stanford University.
From its lumberjack roots to its present-day vibrancy, Woodside’s story is captivating. And at the heart of it all, the Pioneer Saloon Woodside stands as a tangible link to the spirited days of Whiskey Hill, inviting visitors to experience a genuine piece of California history.
