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Macedonia and Serbia
The dissolution of the Byzantine Empire heralded the end of Byzantine rule over Macedonia. Discounting short interruptions, Byzantine authority had extended for more than five centuries. When the Slavs settled in the Balkans, Byzantium was a highly civilized empire and a significant factor in shaping and resolving European political and spiritual issues. The Slavs, including the Macedonian Slavs, were barbarians in the eyes of Byzantium. But while Byzantium was to give much to the Slavs in culture and civilization, the Macedonian Slavs contributed to the Empire as well. The products of the Macedonian peasantry, the fruits of their labors and their service in Byzantine military forces, often in elite units, represented the active creative role of the Macedonian Slavs and their contribution to everyday Byzantine life. Furthermore, "the fresh creative force of the Macedonian Slavic people penetrated into all spheres of state authority and cultural life of Byzantium".
When the Slavs were first occupying the Balkans, Byzantine art had begun to bloom anew. The Church of St. Sophia and Church of St. Irene in Constantinople, Sant'Apollinare Nuovo in Ravenna and the Basilica of Porech date from this period. The contemporary art of the Slavs, however, shows "a lower artistic degree of development". In medieval Macedonia, the history of art is in many ways the history of religious art: in architecture, fresco painting and decorative sculpture. Macedonian art began to develop as an independent and authentic school of art with the coming of Clement to Ohrid. With the building of his monastery in Ohrid (893), argues Dimche Koco, the Macedonian Slavs got "their first great religious and educational center of epochal importance, and conditions were created for a complete change in the development of their aesthetic feelings. With this monastery they accepted and continued the artistic forms created and developed on the territory of Macedonia before their arrival." Whereas architecture in Macedonia had a provincial character, its fresco painting was at a level equal to the finest Byzantine works; of note are the 9th and 10th century frescoes in the Church of St. Sophia in Ohrid and the frescoes of Velyusa and Vodocha.
Stephan Dushan transformed Serbia into a major power in the Balkans in overrunning the western provinces of the Byzantine Empire. In 1345 he proclaimed himself Tsar of the Serbs and the Greeks, and the Archbishopric of Serbia was raised to the level of a patriarchate. Certain significant events in medieval Serbia are connected to Macedonia: for example, the crowning of Dushan as tsar on April 16, 1346, took place in Skopje, and the coronation was attended by the Archbishop of Ohrid. Three years later Dushan, again in Skopje, enacted his Code of Laws, to be later supplemented in Serres.
As often occurs in recently-formed large states after the death of their founder, the Serbian state soon grew unstable after the passing of Tsar Dushan. After his death in 1355, the power of the central authorities rapidly declined and was supplanted by that of the increasingly independently-minded feudal lords. The Serbian Empire was split up into small parts, with several feudal states on or holding Macedonian territory. Elena, Dushan's wife, ruled Serres and the surrounding regions. Caessar Voihna ruled in Drama. Hlapen, Marko's father-in-law, ruled Berroea (Veria) and Voden (Edessa). Despot Oliver ruled a realm extending from Zhegligovo to Belasitsa and Melnik. Gregory ruled Ohrid. Volkashin Mrnyavchevic was zhupan (administrator) of Prilep (in 1365 he proclaimed himself King), with territory extending from Skopje to Prizren; his brother Uglesha ruled over Strymon for about six years. The frequent attacks of Turkish forces forced Uglesha, though a Serbian, to establish closer relations with Byzantium (which had already begun to show renewed signs of weakness). The Ottoman Turks invaded Byzantium without encountering significant resistance, in 1354 conquering Gallipoli and eight years later seizing Edirne. Edirne became the new Turkish capital and the road to the Balkans lay open before them.
On September 26, 1371, O.S., at Chernomen on the Maritsa River, Turkish military forces met the united armies of Volkashin and Uglesha Mrnyavchevich. The Serbian army was decisively defeated, the two brothers were killed on the battlefield, and the Turks were free to further penetration of the Balkan Peninsula. After the defeat of the Mrnyavchevich brothers, Manuel Palaeologus occupied the region of Serres and Chalcidice. Volkashin's son, Marko, recognized Turkish authority and became a Turkish vassal. Macedonia was thus left to the mercy of the new conqueror. At first, the Turks were content with committing small robberies and taking captives; but they soon they expanded their presence. Serres fell in 1383; Shtip, Veles, Prilep, Bitola and Thessaloniki in 1387; and Skopje was taken in 1392. In 1395 at the battle at Rovine, King Marko was killed while fighting for the Turks against the Vlachs, and the Turks assumed direct control over the region. By the end of the 14th century, Macedonia was a Turkish territory. This was the beginning of its five centuries of Turkish rule-or, all too common, misrule.

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