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Populated long ago in the Roman period middle Polimlje was a part of the oldest Serbian state of Raska. In the first manuscripts Prijepolje was mentioned as a square of the Mileševa Monastery. It was an agreement from 1343 concerning the trade of salt from Dubrovnik to Prije-
polje. According to this source it is explicitly said that the square existed in Prijepolje or possibly more than one belonging to the Monastery landed estate, which allows the origins of Prijepolje to be moved back to the time of Mileseva Monastery erection and the foundation of its landed
estate. By the middle of the 14th century Prijepolje had acquired the characteristics of a settlement with the square as a central, distinguished and noticeable space. Its very favorable location, at the crossroads of the important roads, considerably contributed to progress of the Prijepolje Square. The shortest and apparently the most utilized road connecting central and
eastern parts of the Balkans peninsula with the central part of the Adriatic Coast led through Prijepolje. Thousands of merchants and after them the first traveling writers and diplomats of modern times passed along this road.
Although it is said that certain stopping places for caravans existed in Prijepolje at that time, it could be also said there was more than that, for constant arrivals and departures of caravans, changing and meeting the merchants and their escorts had brought new life and expanded
perspectives of the people from this region. Stopovers of merchants and caravans in Prijepolje stimulated its residents to get involved in trade enabling, in that way, the people from close and distant surroundings to gather round the well provided square.
Its highest progress Prijepolje experienced around the middle of the 14th century during the reign of the head of the tribal state of Nikola Altomanovic. Big changes appeared in the middle of the 15th century when this territory and Serbia came under Turkish rule. During Turkish rule the ethnic structure of Prijepolje and its surroundings changed so that beside Christians appeared Muslims as another ethnic group. By the end of the 19th century a powerful Austro-Hungarian monarchy reached the riverbanks of Lim and that started the influences of a new civilization and culture.
After the great world wars that marked the 20th century, and in the second half of the 20th century, Prijepolje experienced its rapid growth and economic development that was stopped by the disintegration of Yugoslavia at the end of the nineties of the last century.