In this article, the two peculiar settlement patterns of the Rough Cilicia will be investigated in detail on the basis of the architectural structures that these settlements have and their geographical locations. By doing so, it is aimed that the characteristic of the urbanization in the region will be determined in order to find out whether the factors that affect this urbanization process are external or internal the Rough Cilicia in the Hellenistic period. In the 4th and 3th century B.C., an colonization period began in the Mediterranean region. These colonization activities were carried out by the Hellenistic kingdoms in order to protect and secure their borders. The Seleucids were vigorous colonizers. The Ptolemaios established numerous colonies throughout the Aegen and eastern Mediterranean. For the Ptolemaios, Cilicia important was the ship building timber supplied. In addition to this material, Cilicia was also a source of manpower. The major elements of Ptolemaic colonization activities in the Rough Cilicia, is the use of the major cities like Nagidos and Kelenderis. The Olbian Territory which is located between Kalykadnos and Lamos rivers is distinctive amongst other Anatolian temple states because of its architectural construction in the Hellenistic Period. The construction period in the Olbian Territory was supported by Seleucus I. Nikator in the beginning of the 2nd century B.C. this period has been observed with historical and archaeological data. The main feature of settlement patterns in the territory is to gather aims in militarian and civilian conditions. This kind of settlement for defence could be called