Vezirköprü, one of the largest districts of Samsun (Amisos), an important port city of the Black Sea, has been the scene of continuous settlement from the Eneolithic Period to the present day thanks to its fertile soils, rivers and its location on an important road. The district, which first appears as a village settlement under the name Phazemon in Strabo, became a city in the Roman Period and was named Neoklaudiopolis. The city called Andrapa in the Byzantine Period took the name Vezirköprü in the Turkish Period and has survived to the present day. The city has witnessed many struggles in this process, including the struggle of the Pontic Kingdom and the Roman Empire. The greatest witnesses of these events were undoubtedly castles and watchtowers. The most famous of these is the Sagylion Castle, localized to Büyükkale in Vezirköprü, which is also mentioned in Strabo. Located on the foothills of Tavşan Mountain, the castle appears to be a typical Mithradates castle due to its location and structures. Although these fortresses built in the region were one of the greatest weapons used by Mithradates Eupator VI against the expansionist policies of the Romans, it is understood that these fortresses were not used on their own but supported by watchtowers selected at the dominant points of the land. Although many fortresses in the Pontos Region have been researched, and some have been excavated, watchtowers have not been sufficiently investigated. This study aimed to shed light on the Hellenistic Period of Vezirköprü by introducing the watchtowers identified during the surveys and the hillside settlements built around them.