In 1305 or 1306, an unnamed bishop of Chariopolis attended a synod called by Patriarch Athanasius I of Constantinople to condemn John Drimys. A priest named Garianos settled in the town shortly after, fleeing from the Bogomils in northern Thrace. In 1316 he was himself accused of Bogomilism, but was acquitted by a synod under Patriarch John XIII of Constantinople. In 1322, Emperor Andronikos III Palaiologos led his army to the town, where he dismissed up to a thousand of his men. In 1344, Emperor John VI Kantakouzenos briefly took up residence in the town. In 1347, the subordination of the bishopric of Chariopolis to Heraclea was formally renewed by imperial "prostagma". In December 1349, Kantakouzenos awarded a "metochion" in the town to the Vatopedi Monastery on Mount Athos. In 1351, the local bishop, whose name is not recorded, participated in a synod against Barlaam of Calabria under Patriarch Callistus I of Constantinople.