Is there a more spectacular concert venue in the Bay Area than the Mountain Winery? Perched in the Saratoga hills like a raven about to take flight over the Silicon Valley, its setting was magical enough to draw Paul Masson from the flatlands of Santa Clara to build a series of exquisite stone edifices that stand to this day.
The steep canyons he cleared to plant vineyards at the turn of the 20th century are still covered with row after row of pinot noir and chardonnay, flanking the bowl where top musicians and entertainers have taken center stage. Look up from the stadium seating at sunset and marvel at the way the western light threads through the rows, turning the hills to corduroy.
Even folks like Derek Quon, general manager of Global Gourmet Catering and Events, who grew up in San Francisco surrounded by beautiful venues like the Opera House, Palace of Fine Arts and the Orpheum Theater, is a little starstruck when talking about the place. “There is really nothing like it anywhere,” Quon says. “It’s just this spectacular gem.”

The sense of history here is ever-present. When Dave House and Bill Hirschman invested in making the facility a bit more modern, adding more seating and additional places for VIPs to hang out and enjoy the ambiance, they gave the place a new lease on life, but took away none of the irreplaceable history. The 12th-century Spanish portal that Masson scored from the post 1906 earthquake rubble of the old St. Patrick’s Cathedral in San Jose still stands above center stage, a reminder of the ardor and creativity of craftspeople inspired by the divine.
Masson built the place for lavish entertaining, and while no one shows up in ballroom attire anymore—jeans and shorts were the uniform of those attending the Common Kings—he would be impressed to see all the areas of the property being used and enjoyed by concert goers, from the Luxury Lounge to the newly expanded Adele’s Garden, where on a recent visit early arrivals seemed to be exploring certain herbs: medicinal, of course. The Garden menu offers flatbreads and a bowl for $29, to enjoy pre-concert.
For an upscale experience, there are Luxury suites, an Overlook Luxury Lounge, Masson Box seating, and VIP season ticket packages, all with a host of amenities including VIP parking and entrance, priority dining service. A new Loyalty Club has four tiers of rewards based on the number of events purchased, starting with four. The chance to see all the old posters and photos of previous performers in the VIP Club Masson is pretty special.

While on-site concessions are available during most shows, dining al fresco at Chateau La Cresta is a memorable experience, with food by Global Gourmet. A recent three-course prix fixe menu offered some great appetizer choices, including Brussels sprouts with bacon, wedge salad with Point Reyes blue cheese, and a tomato and burrata salad with prosciutto and arugula. Mains were Markegard short ribs with mushroom risotto, poached salmon with asparagus, Mary’s rotisserie chicken with broccolini, and rigatoni amatriciana with tomato cream sauce and pancetta.
Desserts are standouts: get all three, because life is short and concerts are long. The limoncello mascarpone cake with raspberry sauce was my favorite, but the triple chocolate mousse was divine, and the pistachio mousse was really good, too. Dinner is $125 per person, and you can add estate wine pairings for each course for $45 per person.
The October musical lineup includes shows by the Marshall Tucker Band, Ziggy Marley, Daryl Hall, George Lopez, and Billy Bob Thornton and The Boxmasters. Boz Scaggs finishes out the season on Oct. 28.

Fans of sparkling wine will be thrilled that bubbly made from estate grapes has returned to the Mountain Winery menu for the first time in over 100 years. There are two options, a Blanc de Blanc and a Brut Rosé, made with pinot noir. And what could be better than indulging in a glass of bubbles as the sun casts a rosy glow over the skyline of San Jose, deepening the shadows on the East Bay hills?
These days, AI might make it easier to find tickets and seating, but it cannot replace the visceral thrill of driving up—and then down—that crazy winding road to the parking lot. And it can’t replace the sense of majesty when, moving down the driveway, the bowl appears as if out of nowhere. When Mother Nature turns out the lights, save for the moon and stars, it glows like a little universe all its own, complete with the soundtrack of the evening. No wonder people come back over and over.
Chateau La Cresta
May–Oct
14831 Pierce Rd, Saratoga
(408) 741-2822

