First written records of Dobrun date from March 16, 1407 and were preserved in a Ragusan contract for the transportation of goods. Sixteen years later, in 1423, the Ragusan envoys informed their superiors that Duke Radoslav Pavlović was heading towards Dobrun, for reasons that remain unknown. The first evidence of a settlement at the foot of Dobrun appeared between these two points in history, in 1421. Namely, in that year the Ragusan envoy found a merchant from Olovo in the town of Dobrun, which most likely refers to the Dobrun sub-town – Pod Dobrun, given that the settlement is described as a “place” (loco), which in Ragusan sources means sub-towns, open squares, but also villages. Duke Radoslav Pavlović stayed in Pod Dobrun (sotto Dobrun) in the spring of 1433. As evidenced by Ragusan sources containing testimonies about the credit indebtedness of local merchants between 1426 and 1429, the sub-town of Dobrun shows certain signs of economic activity. However, it is entirely unfounded to assume that a Ragusan colony existed here as claimed by older historiography. Moreover, Dobrun primarily served as the residence of the nobility, while the economic activity of its sub-town, compared to other settlements under the control of Pavlović, such as Olovo, Prača, Višegrad and Rogatica, was minimal. The above-mentioned data roughly outline the otherwise very scarce written history of medieval Dobrun.
The complex of the town of Dobrun is located in the lower reaches of the Rzav River, east of Višegrad, on the road towards the Ragusan road. In 1469, Ottoman sources refer to a nahiya of the same name, which implies that a county of Dobrun existed there. Near the Dobrun fortress was the Dobrun Monastery (today, it is the Monastery of the Assumption of the Blessed Virgin Mary), whose frescoes enabled the reconstruction of the earlier past of the town of Dobrun. The frescoes depict, in addition to Emperor Stefan Dušan with his wife Jelena and son Uroš, the founder of the monastery, a certain župan (prefect) Pribil with his sons. Župan (prefect) Pribil built the monastery probably in the fourth decade of the 14th century, so it is assumed that in this period he also ruled the town of Dobrun. However, after the construction of the monastery, Pribil became a monk and was succeeded by his sons Stefan and Petar. In the division of Nikola Altomanović’s territory, between Prince Lazar and Ban Tvrtko in 1373, Dobrun belonged to the Bosnian state and was later governed by the Pavlovićs until the Ottoman conquests.
After the conquest of the Bosnian state, the Ottomans formed a special administrative area within the Sanjak of Bosnia, from the conquered possessions that previously belonged to the Pavlovićs, which was referred to as “Land of the Pavlovićs” (Vilayet-i Pavli). The nahiya of Dobrun was also included in this administrative unit. The analysis of the Ottoman census from 1468/1469 came to the conclusion that the town of Dobrun, which corresponds to the former sub-town – Pod Dobrun, had no more than 100 houses. Particularly interesting are the testimonies of Western travel writers who, passing through Bosnia during the 16th century, also visited Dobrun and left behind very vivid descriptions of this town and its surroundings. The well-known Benedikt Kuripešić, during a diplomatic mission sent to Constantinople in the second half of 1530, visited the Dobrun monastery where, as he himself says, he was pleasantly welcomed, and then continued further to reach the town of Dobrun, which he says lies on a cliff. A new mission, led by Leonardo Nagarola and Josip Lamberg, was sent to the sultan in Constantinople the following year, and an individual from their entourage who described this journey mentioned the monastery with the monks and the town of Dobrun. In 1550, the Venetian representative Catarino Zeno passed through the Rzav river valley and, impressed by the beauty of Dobrun, stated that it was an inaccessible fortress where four small fortifications clearly stood out.
The complex of the town of Dobrun consists of two parts, the eastern one, located on the left bank of the Rzav, whose backbone is represented by three towers, and the western one, where a castle with walls and a gate was located on the opposite side of the river. The oldest part of Dobrun’s fortifications is represented by the aforementioned elongated castle with the main tower of irregular construction on the northern side. The castle interior was divided into two partitions, which enabled the defenders to defend each unit separately. Given its dilapidated state, it can only be assumed that one of the buildings within the castle was a cistern. On the east side of the main tower, one wall led towards the cliffs above the river, while another wall blocked the passage between two steep cliffs on the south side. A gate located in the strong front wall protected the only access to the town. According to archaeological remains, there were three towers on the opposite side of the river, and according to Catarino Zeno’s testimony, there were four towers that were not connected. Originally, these towers were used to defend the Dobrun fortress from the south.
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