1.The Fortress on Kaleto
Tsepina stands in the north-eastern part of the Chepino basin, on a steep peak the local people call Kaleto, some 1,100 metres above sea level and a few kilometres from today's village of Dorkovo. Two water cisterns lined with waterproof plaster supplied the defenders. Excavations have also revealed a church in the fortress and fragments of relief sculpture. Emperor Theodore II Laskaris calls Tsepina a "famous and renowned fortress" — the strongest, the most inaccessible and utterly impregnable.
2.The First Capital of the Despot Slav
After Kaloyan's death his sister's son Alexius Slav, one of the Asens who would not recognise Boril's rule, declared himself independent ruler of the districts in the Pirin and the Rhodopes. His first capital was Tsepina. In his own sigillion of 1220 Slav writes that he had moved from Tsepina to his new domain of Melnik — a more convenient and more prestigious town in the Struma valley.
3.War with Nicaea (1246–1256)
After Ivan Asen II's death the Nicaean emperor John III Vatatzes advanced into Thrace and with hardly any resistance took Stanimaka, Tsepina and the towns of the Rhodopes; the Maritsa became the border. At the end of 1254 the young Tsar Michael II Asen took advantage of Vatatzes' death and sent troops into the Rhodopes. The local Bulgarian population, Akropolites stresses, accepted Bulgarian rule willingly, and the Bulgarians quickly took Stanimaka, Perushtitsa, Krichim, Tsepina, Ustra, Perperakion and the district of Achridos — most of the fortresses being unfinished and short of weapons.
The new emperor, Theodore II Laskaris, answered swiftly. He recovered all the freed towns — except Tsepina. In the autumn of 1255 Theodore II gathered the whole army at Adrianople, countless carts for the siege engines and supplies, archers and mace-bearers, and set out against the fortress. At Makrilivada the army was caught in a heavy snowstorm and most of the commanders urged the emperor to turn back, but he pressed on. Tsepina held, however: although Theodore directed the siege in person, every assault was beaten off and the emperor withdrew.
The fortress that did not fall to arms was lost to diplomacy. In 1256 Bulgarian envoys led by the Rus' prince Rostislav Mikhailovich, Michael II Asen's father-in-law, came to Theodore II and offered peace. Rostislav accepted the Byzantine terms without objection: the borders would stay as they were, and the Bulgarians undertook to hand over Tsepina. The treaty was concluded at the end of June or the beginning of July 1256.
4.The Nine Fortresses (1344)
Nearly a century later Tsepina returned to Bulgarian hands. In 1344, at the height of the Byzantine civil war, the regent Anne of Savoy sought Ivan Alexander's help against John Kantakouzenos. As his price he demanded nine fortresses at the foot of the Rhodopes, among them Tsepina, Stanimaka and Plovdiv. The district he obtained, stretching from Plovdiv and Perushtitsa to Tsepina and from there south-east to Kosnik, was mostly Bulgarian in population but had yet to be drawn into the tsardom.