During these ages Haskovo and Haskovo region continued to experience the advantages and disadvantages of the big military and trade thoroughfare, which then connected the Byzantine capital Constantinople with Central and Western Europe.

    From the middle of the 6th century along the Maritsa valley the mobile Slav bands started their raids on Thrace and the Aegean. A little later the proto-Bulgarians arrived. In the last quarter of the 6th century and the beginning of the 7th there was a process of massive Slav colonization in the interior of Thrace. An important moment in the settlement history of Haskovo was the Slavs’ settlement in the territory of the present-day residential district of Hissarya towards the end of the 8th century.

    The Haskovo area entered the bounds of the Bulgarian state at the outset of the 9th century. The medieval settlement in the area of Hissarya had a central position in the system of fortresses in the region, which played a distinct part in the defence of the borders of the new Bulgarian state. The imposition of Christianity, the introduction of the Slavonic script and letters, and liturgies in the Slavonic language were conducive to the rapid integration of the local population in the process of building a united Bulgarian state. Archaeological finds confirm the change in lifestyle and culture of the local people and the creation of all prerequisites for easier adoption of the achievements of the Byzantine civilization. During the reign of Simeon the Great the importance of the settlement grew and a second fortified wall had to be erected, which encompassed a several times larger area – the so-called outer city. The layout of the city was similar to that of the other cities in medieval Bulgaria. Analysis of the fortress and the finds uncovered in it characterize it as a fortified settlement. Medieval Haskovo was the economic and military center of a considerable district. According to the history by hieromonk Spiridon of 1792, the medieval city was called Marsa.

A bronze bust of Dionysius – an ornament on a ch ariot (2nd–3rd cc.)	A bronze tablet with Dionysius embossed on it (2nd c.)

    In the late 10th and early 11th centuries the Haskovo Fortress, witness of many bloody battles, was in decline. It was among the first strongholds to suffer the blows of the Byzantine expansion, renewed during the reign of Emperor Basil II Bulgaroctonus. After the conquering of Bulgaria by Byzantium, in the late 10th century the conditions for the city development changed. The fortified walls were ruined, the city lost its trade and crafts and its military nature and acquired an agrarian character. The population moved across the river. Later the Ottoman conquerors found it there.

    A most remarkable historical event from the time of the Second Bulgarian State (1187-1396) in the 13th century, concerning Haskovo and the region, was the famous Battle of Klokotnitsa (1230). Then the legendary Bulgarian ruler King Ivan Asen II defeated the numerous army of the Byzantine Despot Theodore Comnenus. The victory at Klokotnitsa and the subsequent events made Bulgaria a leading political power in the Balkan Peninsula. Near and distant countries reckoned with it.

    From the 12th to the end of the 14th century the fortress in the area of Hissarya and the old city were transformed into a necropolis. The rich burial finds are evidence of the fact that in this period the medieval Haskovo settlement enlivened. The expensive women’s jewellery, abounding in the necropolis, were worn by the wives of wealthy merchants and craftsmen. The coins, artistic table ceramics made in the sgraffito technique, and many other objects speak of prosperity too.

    Glass and bronze bracelets, silver earrings, rings, etc. made with great craftsmanship, vivid testimony to the Old Bulgarian jewellery art in these parts from the time of the Second Bulgarian State