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The history of Skopelos probably started in the Neolithic period, according to archaeological findings from the island. Its ancient name was Peparethos, as mentioned by Thucydides. Around 1600 BC, Minoans from Crete settled the island and their mythical king Staphylos, son of Dionysus and Ariadne, introduced the wine to the locals. After the Mycenaean period, Skopelos was occupied by the Dolopians (people from Thessaly) who used the island as a military base. Then people from Chalkis, Evia island, came and founded three colonies: Panormos (today called Glossa), Selinos (today called Loutraki) and Peparithos (the present Skopelos Town). They developed trade and Skopelos enjoyed a period of prosperity.
The 5th century marked the beginning of the Persian Wars during which the island remained neutral. At the end of the wars, Skopelos joined the Delian League and implanted a democratic political system. The winners of the Peloponnesian war, the Spartans, replaced the democratic system of the island with an oligarchic political system. During Roman times, trade reflourished and wine export expanded in other areas of Greece. In the 2nd century AD, Ptolemy the Geographer is the first one to refer to Peparithos as Skopelos, probably as a reference to the many reefs surrounding the island. Since then, the island kept this new name. Christianity appeared in Skopelos in the 3rd century AD and spread quickly.
In the 4th century AD, the seat of an archbishop was established and the first archbishop of Skopelos was Reginos, who later became a saint and the protector of the island. In 1207, Skopelos is occupied by the Venetians and after 1276, with the decline of the Byzantine fleet, the island becomes a shelter for pirates. The years that follow, from 1453 to 1538, Skopelos falls under the Venetian rule for the second time. The same year, the Turk pirate Barbarossa attacked the island and slaughtered its inhabitants. Some of them survived and escaped to Evia and Thessaly, returning years later to their homeland. In the location Sedoukia, there are the legendary pirate graves. The island is set free from the Ottomans after the Greek Revolution of 1821.