Temperate trees require low temperatures during winter and subsequent warm conditions in early spring to flower and eventually bear fruit. Many parts of the Mediterranean region feature winters with low and sometimes marginal chill accumulation. To assess historic and future agroclimatic conditions for cultivating temperate trees (including almonds, pistachios, apricots, sweet cherries and apples), we mapped winter chill throughout this important growing region. We used on-site weather records (1974–2020) to calibrate a weather generator and produced data for historic and future scenarios. To broaden our analysis, we spatially interpolated chill for the whole Mediterranean basin. We supplemented our simulation outcomes by collecting expert knowledge (from farmers and researchers) regarding observed climate change impacts on temperate orchards as well as future risks and concerns generated by climate change. Results showed that northern African growing regions have experienced major chill losses, a likely cause of the irregular and delayed bloom highlighted by experts. The same regions, together with southern Europe, may lose up to 30 Chill Portions by 2050 under a moderate warming scenario. For the future, experts foresee increasing risk of spring frost in early-blooming cultivars, exacerbated bloom-related problems and increasing occurrence of heat waves. Our results provide evidence of likely climate change impacts on temperate orchards. Expert knowledge proved instrumental in interpreting the simulation results as well as in orienting climate change adaptation strategies. The results we present are useful for farmers and orchard managers planning new plantings, as well as for researchers and policy makers developing strategies to adapt fruit orchards to the impacts of climate change.