The hook
One of the oldest surviving wineries in California still stands on the Monte Bello ridge above Cupertino — an 1870s Italian homestead where peacocks strut the grounds and you can taste wine on the porch of a building older than the state's wine industry.
01Why it's worth it
Vincenzo Picchetti emigrated from Italy in the 1800s, bought a parcel on the ridge he called "Monte Bello" (beautiful mountain), and by 1877 was making wine; the main winery his family built in 1896 still stands, making Picchetti one of the oldest continuously recognized winery sites in California. What makes it a genuine oddity rather than just old is the atmosphere: it's now a public open-space preserve wrapped around a preserved homestead, and the peacocks — descendants of the ranch's old menagerie — wander the yard and roost in the trees, screaming and fanning among the century-old buildings. A private lessee still runs tastings in the historic winery, so you can sip on the picnic lawn under the oaks with peacocks underfoot, then walk 3.7 miles of trails up into the ridge's oak woodland. History, birds, and a glass of wine on a mountain the Ridge Vineyards world made famous — an easy, strange, lovely South Bay afternoon.
02How to experience it
Montebello Road off Stevens Canyon Rd, Cupertino (free preserve; the winery tasting room keeps its own hours). Do the short homestead loop for the buildings and peacocks, taste on the lawn, and extend onto the Zinfandel or Orchard trails for the ridge views. Pairs with Rancho San Antonio or Monte Bello's open space nearby.