Vineyards are expanding rapidly in California's north coast due to a booming wine market. In Sonoma County, much of this expansion is occurring on hillsides that harbor California's remaining oak woodlands. The pattern of vineyard development is influenced by physiographic, environmental, and land use variables. Spatially explicit models are used to reveal where vineyards are likely to be established in the future based on recent trends in vineyard expansion. Changes in oak woodland connectivity, effects of different environmental policies, and areas of land use conflict are examined to strive for sustainable agriculture on a landscape scale.