The aim of this narrative review is to provide an overview of the connection between Thessaly and the development of medicine from ancient Greek mythology to contemporary times. From Chiron to Asclepius, from Asclepius to Hippocrates, and from Hippocrates to the true Hippocratic epidemiologist Dimitrios Trichopoulos, a plethora of myths and facts indicate the strong and perpetual alignment between Thessaly and the science of medicine.