Past, present, and projected fluctuations of the hydrological cycle, associated to anthropogenic climate change, describe a pending challenge for natural ecosystems and human civilizations. Here, we compile and analyze long meteorological records from Brno, Czech Republic and nearby tree-ring measurements of living and historic firs from Southern Moravia. This unique paleoclimatic compilation together with innovative reconstruction methods and error estimates allows regional-scale May-June drought variability to be estimated back to AD 1500. Driest and wettest conditions occurred in 1653 and 1713, respectively. The ten wettest decades are evenly distributed throughout time, whereas the driest episodes occurred in the seventeenth century and from the 1840s onward. Discussion emphasizes agreement between the new reconstruction and documentary evidence, and stresses possible sources of reconstruction uncertainty including station inhomogeneity, limited frequency preservation, reduced climate sensitivity, and large-scale constraints.