By the end of the XIII century, Skopje often was captured and re captured by the Byzantine and Bulgaria and vice versa. In 1282 King Milutin captured Skopje and annexed it to the Serbian state. After the change of several rulers, Skopje in 1392 fell into the hands of Ottoman Turks.
Detailed description of the Skopje Kale (Fortress) gives the traveler writer Evliya Çelebi:
"It is a fortified city, firm and strong with double ramparts. City Gate and walls are built of well formed stone which shines like polished. Such refinement and art in processing cannot be seen in any other city. The city lies in the center of Skopje. It is a high capital building with five pentagon shape. Wall, which surrounds the city on all sides, is high up to fifty “arshins (1 аршин = 65 – 75 cm)”. The city is decorated with seventy bastions and three Demir (Iron) ports south-east side, and in the courtyard every high port are a lot of guards. The door and walls of the lobby are decorated with a variety of weapons and tools needed for the weapons. There is no other position which dominates the town as the Fortress which stands tall on the rocks so that it sees the whole plain.
On the western side flows the river Vardar. That side has a path leading through the caves to the "water tower" which is located on the banks of the river. Because that side of town is broke, scary with big depths, there are no trenches there. The eastern, southeastern and northern side of the city, are deep trenches. On that side, the gate is a wooden bridge thrown over trench. Guards sometimes raise the bridge with Winch and so create a dam in front of the gate. Above this port is inscription which tells when this port was repaired:
"Wise son Mehmed Khan in the year one eight hundred and fifty" (1446 AD).
In this position this fortress was found by the Austrian general Piccolomini in 1689, and from his letter to the Emperor Leopold we can see that:
"... fortress is built on an old way, now completely defenseless and without water, there is no room for cavalry "...
From travel writers visiting the fortress in the nineteenth century we learn that here were magazines and gun powder depot, war hospital and prison.
The 1963 Skopje earthquake had made the fortified city great harm. After the earthquake, measures were taken for the conservation and restoration of its walls. After that event were conducted archaeological excavations.
From May 2007 started extensive excavations of the fortress Kale, which are supposed to highlight a number of issues related to this site.