Small, diversified farms on California’s Central Coast have been dry farming for decades, allowing farmers to use water stored in soils from winter rains to grow tomatoes and other vegetables with little-to-no irrigation in summers without rainfall. As recent water shortages in California have forced a reckoning with the precariousness of the state’s water supply, policy groups and the general public have become increasingly interested in dry farming as a promising means of achieving water conservation goals. Academic research on this practice, however, has been scarce. Amid growing urgency to develop low-water agricultural systems in the state, we interviewed 10 Central Coast dry farmers, representing over half of the commercial dry farm operations in the region where this practice was developed, to collaboratively answer 2 central research questions: (1) What business and land stewardship practices characterize successful tomato dry farming on California’s Central Coast? (2) What is the potential for dry farming to expand beyond its current adoption while maintaining its identity as a diversified practice that benefits small-scale operations? We summarize farmers’ wisdom into 9 themes about current dry farm practice, its potential for expansion and future opportunities. We also synthesize farmer-stated environmental constraints on dry farm feasibility into a map of suitable areas in California. As we consider how dry farming might expand to new areas and operations, we highlight dry farming’s history as an agroecological alternative to industrial farming in the region and the need for careful policy planning to maintain that identity. In examining this California Central Coast dry farming system, we ask if and how it can enhance the viability of nonindustrial farming operations as the food system adapts to less water availability. Because policies that encourage dry farm expansion could change economic landscapes in which dry farming operates, we caution that well-intentioned policies could edge small growers out of dry farm markets if not carefully designed. At the same time, we emphasize the opportunity for dry farm tomato systems to model an agroecological transition toward water savings in California.