The present article analyzes four Hellenistic funerary stelae from the modern village of Gephyra on the Axios River, the site of the ancient city Herakleia. The style of the monuments and the letter forms of the inscriptions allow us to establish their relative chronology and to date them to the end of the fourth and the beginning of the third century B.C.E.; our reconstruction of the stemma of the persons named in the inscriptions suggests that they may belong to the same family. The two stelae with reliefs provide valuable information about the armament and equipment of cavalry and infantry in Hellenistic Macedonia. For example, the horseman carries a shield, a detail of paramount importance, since it suggests an early date for the introduction of the cavalry shield in Greece, sometime prior to Pyrrhus’ return from his western expedition. The offensive and defensive weapons of the footman strengthen previous conclusions that the heavily armed Macedonian infantry was equipped according to specific standards dictated by rank.