Rene di Rosa was born in Boston in 1919 and graduated from Yale, where he edited the Yale Daily News. After serving as a Navy lieutenant in World War II, he took a reporter's job at the San Francisco Chronicle in 1950. The assignment placed him near North Beach during one of the most explosive periods in Bay Area art history. Abstract Expressionists, Beat poets, and the emerging Funk Art movement were all working within blocks of each other, and di Rosa began buying their work before most galleries knew their names. When he moved to Napa in 1960 and enrolled in viticulture classes at UC Davis, he discovered that many of the artists he admired were teaching there. Robert Arneson, Roy De Forest, Manuel Neri, and William T. Wiley were all art professors at Davis in the mid-1960s. The friendships di Rosa formed in lecture halls and studio visits became the backbone of his collection.

Di Rosa planted vines and established Winery Lake Vineyards in 1963, eventually covering some 250 acres. The property's lake began as a modest irrigation pond dug by WPA workers in the 1930s. Di Rosa built a dam and expanded it into an approximately 35-acre body of water he named Winery Lake, its surface reflecting both the surrounding hills and the sculptures he increasingly placed along its banks. In 1986, he sold the vineyards to Seagram and used the profits to establish the Rene and Veronica di Rosa Foundation. His wife Veronica, a Canadian-born watercolorist and sculptor trained at the Emily Carr School of Art, had shared his vision of building an art park before her death in 1991. The property opened to the public in 1997 and became an independent nonprofit in 2000. Today the 217-acre site encompasses multiple galleries, a sculpture meadow, and land protected in perpetuity under the Napa County Land Trust.

In July 2019, the foundation's leadership announced plans to sell most of the 1,600-work collection, retaining only several hundred pieces. The reaction was immediate and fierce. Artists whose work hung in the galleries organized petitions. Mark di Suvero, Peter Saul, and dozens of others publicly protested what they saw as a betrayal of di Rosa's vision. The collection represented something rare: not a billionaire's trophy acquisitions, but a half-century record of Bay Area artistic experimentation, from the ceramic irreverence of Robert Arneson to the conceptual investigations of Paul Kos and the visionary paintings of Jay DeFeo. Selling it off would scatter a community's creative memory across auction houses. Under new Executive Director Kate Eilertsen, di Rosa reversed course in 2021, committing to preserve the collection. The crisis had revealed how deeply the art community considered these works their own.

Di Rosa's programming reflects the landscape it inhabits. Rotating exhibitions in the galleries draw from the permanent collection and feature emerging Bay Area artists, but the site's identity extends well beyond its walls. The sculpture meadow places large-scale works in dialogue with the oak-studded hills of the Carneros. Birdwatching walks follow the shores of Winery Lake, where egrets and herons pick through the shallows beneath steel and stone installations. Summer camps bring children to make art alongside the collection. A 2007 PBS documentary, Smitten, directed by Nancy Kelly, captured the essence of what di Rosa built: not a museum in the traditional sense, but a place where art and the natural world occupy the same ground without apology. Rene di Rosa died in 2010 at age 91, but the landscape he shaped continues to evolve, each new exhibition adding another layer to a property that has been reinventing itself since 1886.