In island legend Skopelos was founded by Staphylos (Greek for grape), one of the sons of the god Dionysos and the Princess Ariadne of Crete.

Historically, in the Late Bronze Age Skopelos, then known as Peparethos, was colonized by Cretans who introduced viticulture to the island.

[citation needed] Skopelos reflects this trend and the local authorities are hard-pressed to deal with the increased traffic and parking issues.

[6] The town of Skopelos was honored as a Traditional Settlement of Outstanding Beauty (19/10/1978 Presidential Decree 594,13-11/78, signed by President of Greece Konstantinos Tsatsos).

Some restrictions stipulate that no new buildings shall be of more than two stories, there must be a sloped ceramic or stone roof in the traditional style, and doors, windows and balconies be made of wood.

The oldest existing ecclesiastical structure is the basilica of Agios Athanasios built in the 11th century and located in the Kastro area.