Climate change poses a major sustainability challenge, with potential far-reaching economic and social impacts, including fluctuations in agricultural yields and subsequent volatility in the availability and prices of essential food resources. In this study, we analyze the changes in climatic variables and agricultural yields for main crops cultivated in the Abruzzo Region (Central Italy), as well as their reciprocal correlation pattern in the time range, 1952–2014. Central Italy exhibits a well-developed agricultural sector and is characterized by a Mediterranean climate; given its proximity to the semi-arid and arid North African climate zone, such a region may be particularly vulnerable to climate change impacts. The analysis reveals an increase in drought intensity and persistence, starting from the 1980s, with a shift towards more temperate conditions in winter months and a transition to a warmer and more arid climate during the summer season. Moreover, the study identifies an overall increase in the correlation magnitude between crop yield fluctuations and climatic variables in the period 1983–2014 compared to that during the previous thirty-year time range. This finding can be interpreted as a change in the resilience (or increased vulnerability) of the agricultural production system to climate change. This work can be thus considered as an interesting case study in the Mediterranean region, offering valuable insights for constructing probabilistic models of fluctuations in agricultural production possibly induced by climate change.