During the Hellenistic years (end of 4th – 1st c. BC), Skopelos becomes the centre in many struggles among the Successors, as well as the struggles between Romans and Macedonians.
In late Classical and Hellenistic times, Peparithos cuts copper coins and it seems that the trading of wine –the famous peparithos wine- is still prospering.
There is mention of the island in various sources of ancient years, and in fact Aristotle refers to the famous peparithos wine as a well-known wine and aphrodisiac.
In Classical and Hellenistic times, it is worth mentioning that many temples were built, as well as fortifications in various parts of the island, of which there are important remains.
In 146 BC the Romans conquer the Greek territory. Under Roman occupation, Peparithos seems to maintain some independence, as portrayed by the copper coins that were cut during this period. In the ancient sources of the era, there is minimal mentioning of the island of Skopelos. However, the name Skopelos appeared for the first time during Roman years, in texts by Ptolemaios (form the 2nd c. BC), and this is probably due to the many reefs and shelves around the island.
Christianity was developed and spread early. In the 4th c. AD the island is dominated by the figure of bishop Riginos, who contributed to the spreading of the new Religion in the Northern Sporades. In 363 and during the Persecutions under Julian, Riginos was murdered and the Church pronounced him a saint. Riginos, bishop of Skopelos, is commemorated as a saint in the Orthodox Church on February 25 and he is the patron saint of the island.