Prijepolje was mentioned for the first time by "Gijom Adam" in 1332 while it was part of Dubrovnik's sphere of influence. According to historical sources, Prijepolje developed as a road settlement for caravans along the route known as "Dubrovnik's road", a road connecting the central and eastern Balkans with the middle Adriatic coast. The caravan route traversed both mountainous and heavily forested areas, which could prove dangerous to travelers. Local villagers were tasked with protecting local roads, due to the statute which said, "If, on the road, someone has been killed or has had a bullet stuck into his body, let the local guardians gather together to pay the damage. Hitting by one small drum, the passers by would know that there was no danger".