According to the legend, Skopelos was founded by Staphylos or Staphylus (Greek for grape), one of the sons of the god Dionysos and the princess Ariadne of Crete.
Historically, in the Late Bronze Age the island, then known as Peparethos or Peparethus was colonised by Cretans, who introduced viticulture to the island. Perhaps because of the legend of its founding by the son of the god of wine, the island was known throughout the ancient Greek cities of the Mediterranean Sea for its wine. The play Philoctetes (first performed at the Festival of Dionysus in 409 BC) by Sophocles includes a wine merchant lost on his way to "Peparethos, rich in grapes and wine".Pliny the Elder, in his book "Natural History" writes:
"The physician Apollodorus, in the work in which he wrote recommending King Ptolemy what wines in particular to drink -- for in his time the wines of Italy were not generally known -- has spoken in high terms of that of Naspercene in Pontus, next to which he places the Oretic, and then the Aeneatian, the Leucadian, the Ambraciotic, and the Peparethian, to which last he gives the preference over all the rest, though he states that it enjoyed an inferior reputation, from the fact of its not being considered fit for drinking until it had been kept six years."
In 1936 excavations in the area of Staphylos / Velanio uncovered a royal tomb of the era of Mycenaean Greece. The island was briefly under the control of the city-state Chalcis, Euboea since at least the 8th century BC.
Skopelos became part of the First Hellenic Republic under the London Protocol confirming its sovereignty (3 February 1830).
During World War II, Skopelos fell under Axis occupation. At first it was occupied by the Kingdom of Italy (June 1941 - September 1943) and then by Nazi Germany (September 1943 - October 1944).
Skopelos and the rest of Greece returned to democratic style government in 1944.