Background: Winter chill is one of the defining characteristics of a location’s suitability for the production of many tree crops. We mapped and investigated observed historic and projected future changes in winter chill in California, quantified with two different chilling models (Chilling Hours, Dynamic Model). Methodology/Principal Findings: Based on hourly and daily temperature records, winter chill was modeled for two past temperature scenarios (1950 and 2000), and 18 future scenarios (average conditions during 2041–2060 and 2080–2099 under each of the B1, A1B and A2 IPCC greenhouse gas emissions scenarios, for the CSIRO-MK3, HadCM3 and MIROC climate models). For each scenario, 100 replications of the yearly temperature record were produced, using a stochastic weather generator. We then introduced and mapped a novel climatic statistic, ‘‘safe winter chill’’, the 10% quantile of the resulting chilling distributions. This metric can be interpreted as the amount of chilling that growers can safely expect under each scenario. Winter chill declined substantially for all emissions scenarios, with the area of safe winter chill for many tree species or cultivars decreasing 50–75% by mid-21st century, and 90–100% by late century. Conclusions/Significance: Both chilling models consistently projected climatic conditions by the middle to end of the 21st century that will no longer support some of the main tree crops currently grown in California, with the Chilling Hours Model projecting greater changes than the Dynamic Model. The tree crop industry in California will likely need to develop agricultural adaptation measures (e.g. low-chill varieties and dormancy-breaking chemicals) to cope with these projected changes. For some crops, production might no longer be possible.