The land of the municipality of Radomir is abundant in vestiges of the Bulgarian Middle Ages, the physical evidence of which is the large number of ruins of settlements, ancient churches and monasteries. Byzantine chronicles are emphatic that the population from the upper reaches of the Struma River has always been ethnically pure Bulgarian communities in the Middle Ages. The fact is reflected in the names of the villages and localities with some of them being named after medieval Bulgarian tsars and boyars. The name of Radomir city falls into the same category of Bulgarian names. A legend has it that the city was called after a Bulgarian voivode of the same name. Bulgarian history gives a number of examples of the same name: King Gavril Radomir of Bulgaria, the fifth son, Radomir of King Ivan Vladislav of Bulgaria, renowned Bulgarian man of letters of the 13th c., Radomir, who wrote the Radomir’s Psalter, etc.
In the Middle Ages, the valley of Radomir has often happened to be the scene of fierce battles waged by Bulgarians against Byzantium, as it is crossed by a strategic road to the Aegean Sea, trailing along the Struma riverbed, well-know even to Romans, which road had never lost its importance all along, including the Middle Ages. In many of the legends told by the locals about the ancient ruins on the high hilltops, where arrowheads and medieval coins have been unearthed, the names of Bulgarian Kings Samuil and Ivan Shishman, as well as of other medieval sovereigns and voivodes are involved.
The ruins of Malo and Goliamo Gradishte atop Golo Bardo, the ruins above the village of Dren, where a locality, called The Tsar’s Tree, is situated, the ruins on the hillside between the villages of Vladimir and Dolna Dikanya, as well as those rising above the villages of Drugan, Radobosh, etc., bear tacit witness to the dramatic events.