In the 14th century, after the destruction of the Byzantine Empire, Radoviš found itself in the Serb medieval state. In 1361, the tsar Uroš sojourned in Radoviš. During the Ottoman Empire, in the 17th Century under the Kyustendil sanjak, it belonged to the diocese of the Kustendil metropolitan. At that time, the town had 3,000–4,000 inhabitants.
The Medieval period of Radoviš is characterized by the expansion and development of Radoviš and its surroundings. The economical, political and educational histories of the region can attest to this. In the territory of the Municipality of Radoviš are located both explored and unexplored archeological sites, monasteries, and churches all of which are truly a part of a rich heritage of culture monuments. In addition, this territory dates back to prehistoric times and contain artifacts from the Neolithic, Eneolithic, Halsta and the Bronze Ages. In the time of Philip the Second and Alexander the Great, poems about the territory of the Municipality of Radoviš were written. Also, numerous remains date back to Roman times and even earlier. Additional findings include ancient settlements,
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