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The first reference to Metsovo was made in 1380 A.D. in the chronicle of the Philanthropinos brothers Proklos and Komnenos.

At first, Metsovo used to be a small settlement of shepherds. Later, due to its important geographical location, Metsovo acquired a number of privileges that contributed to its survival and accelerated the development course in difficult times.

In 1430 A.D. it is mentioned that sultan Murat II granted privileges to the residents of Metsovo, as a reward for the good behavior of the Metsovite guards of Zygos to the Ottoman tr?ops of Sinan Pasha, who were heading for Ioannina. Sultan Mehmet IV renewed the privileges in 1659 A.D. Based on these privileges, Metsovo and the surrounding villages of Malakasi, Milia, Anilio, Votonosi, Palia Koutsoufliani (Platanistos) and Derventista (Anthochori) formed a federation, an autonomous, democratic state within the limits of the Ottoman Empire. The privileges granted to Metsovo, with the exception of the Patriarchal Hexarchy that was preserved until 1924, were abolished in 1795 by Ali Pasha. In 1700 A.D., a self-catering Greek school was founded in Metsovo to become one of the most important education centers, staffed with the eminent teachers of that time. Metsovo suffered considerable destruction on March 27, 1854 by the Ottoman troops of Abdi Pasha. This became known as the "Grivas disaster". Following the "Grivas disaster", Metsovo experienced a unique progress that was attributed to the large number of benefactors, who hailed from the town and offered substantial sums of money in order to contribute to its re-establishment.

Metsovo was liberated from the Turkish yoke on October 31, 1912 by forces of the Greek Army and volunteers from Crete and Epirus.

Decisive role in the economic and cultural development of Metsovo played the Baron Michail Tositsa Foundation, established in 1948 by the Baron himself at the instigation and the encouragement of Evangelos Averoff Tositsa.

Among the great men of Metsovo are: the Metsovian neomartyr Nicholaos (+May 17, 1617), the teachers of the nation during the Turkish occupation Nicholaos Tzartzoulis, Parthenios Katzioulis, Dimitrios Vardakas, Tryfon the priest-monk, Adam Tsapekos, the national benefactors George Averof, Nicholaos Stournaras, Mihail Tositsa, Triantafyllos Tsoumagas, Kyriakos Flokas, Baron Michail Tositsa, the freedom fighters Dimitrios Ipatros, Anastasios Manakis, Ioannis Gadelos, Apostolos Hatzis, Dimitrios Zamanis and the politician and benefactor Evangelos Averof Tositsa.

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