Alonissos has been geographically somewhat removed from the events recorded in the history books since ancient times. Nevertheless, over the centuries, a diverse and rich life has developed on the island, shaping its own history.

The earliest evidence of human presence in the Aegean dates back to the Neolithic period (10,000 BC - 2200 BC) and was discovered in the 'Cave of the Cyclops' on the island of Gioura northeast of Alonissos. Settlements found in the bays of Agios Petros on Kyra Panagia and Kokkinokastro on Alonissos also indicate that the island was inhabited early on.

Historians Herodotus and Thucydides (both lived around 450 BC to 400 BC) recount the former maritime power of King Minos of Crete, who controlled the sea routes and founded colonies on the Aegean islands. It is said that in the 16th century BC, King Minos sent Prince Staphylos, the son of his daughter Ariadne with the god Dionysus, to Skopelos. His brother Peparithos accompanied him in colonizing the island and named it Peparethos. They brought grapevines and olive trees to the island. There is disagreement about whether they also settled Alonissos, then called Ikos. However, it is undisputed that Ikos was known in antiquity for its extensive wine cultivation and production. Amphorae with the inscription IKION were found in ancient cities on the Black Sea, in Athens, Pelia, and Alexandria, emphasizing the island's importance. The inscription IKION indicates that the wine originated from Ikos.

In the 7th century BC, Ikos, along with Peparethos and the other Sporades islands, became a colony of Chalkis, the most important city on Euboea. During this time, the Sporades experienced a period of independence and prosperity. The geographer Skylax (living in the late 6th century BC) mentions two settlements on Ikos."

As an ally of Athens, the island was occupied by Sparta after the Peloponnesian War (431-404 BC). After regaining independence in 395 BC, Ikos joined the Second Athenian League until its dissolution in 355 BC. The independence of Ikos was lost after the Peace of Athens with Philip II of Macedonia, and like all the Sporades islands, it came under Macedonian rule. During the Macedonian Wars in the 2nd century BC, Philip V of Macedonia fought against the growing power of Rome for influence in Greece. He feared that the islands could be used as strategic bases against him. Therefore, he ordered the destruction of the cities on Peparethos and Skiathos as well as the depopulation of the islands. It is highly likely that Ikos also suffered this fate. Nevertheless, Rome gained supremacy over the region after 146 BC. This rule lasted until late antiquity, as the Western Roman Empire gradually collapsed (476 AD), but the Byzantine Empire in the East continued until the fall of Constantinople in 1453. The history of the Sporades fluctuated between apparent autonomy and the oppressive tax burden imposed by Rome.

After the Fourth Crusade (1202-1204), the island, now known as Chelidromia, fell under the rule of the Venetian family Ghisi. However, in 1267, the Ghisis were expelled by the Veronese admiral Licario on behalf of Constantinople. Chelidromia remained under Byzantine control until 1453.
After the fall of Constantinople, the inhabitants once again sought refuge with the Venetian Republic, which henceforth took over control. However, the Venetians were unable to significantly improve the lives and security of the residents. Pirate attacks forced the population to stay within the fortified Kastro. They could neither tend to their fields nor go fishing. In 1538, the island fell victim to a raid and plundering by the pirate Khaireddin Barbarossa. Many residents lost their lives, while the survivors were either enslaved or fled the island. Barbarossa left the island to other pirates, who for centuries spread terror throughout the northern Aegean, hidden in countless coves and caves. The island remained virtually uninhabited in the following decades until the late 16th century. Only then did a gradual migration begin from neighboring islands and the mainland.

During the War of Independence from 1821 to 1829, Greece rose up against Ottoman rule and sought independence. The conflicts ended in 1829 with the Treaty of Adrianople. According to this agreement, the Ottoman Empire recognized the independence of Greece. After liberation, the island was named Alonissos and established as "Dimos Alonnisou" (Municipality of Alonissos) before officially passing from the Ottoman Empire to the Kingdom of Greece in 1830. The inhabitants led a modest but peaceful life, dedicating themselves to animal husbandry, agriculture, fishing and reviving wine production, which once thrived under the legendary Prince Staphylos.

In April 1941, German troops captured the islands of Skiathos, Skopelos, Alonissos and Skyros. The occupation period was characterized by oppression and exploitation of resources. Some locals joined the Greek resistance movement and carried out acts of sabotage against the German occupiers. The Northern Sporades were only liberated from the German occupiers in October 1944.

In 1950, the island was hit by phylloxera, which destroyed almost all vineyards within 10 years. In 1965, the Chora was struck by an earthquake, which destroyed numerous houses and left the village largely abandoned. However, in the early 1970s, the first tourists arrived, and slowly a new chapter in the island's history began.

Alonissos, like numerous other Greek islands, has undergone a transformation in its economy and way of life. Tourism has gained importance, and today the island is famous for its beautiful beaches, crystal-clear waters, and picturesque villages. Additionally, Alonissos is part of the Alonissos - Northern Sporades Marine Park, established in 1992. The park aims to protect rare plant and animal species, particularly the Mediterranean monk seal (Monachus monachus). Through sustainable tourism, the natural beauty of the islands is intended to be preserved for future generations.

Alonissos carries within it a rich and diverse history. The multitude of names, from Ikos to Chiliodromia, Iliodromia, Liadromia, and Alonissos itself, attributed to this small island, gives the impression of several islands in one. Over time, a variety of people from diverse backgrounds have lived here. It's as if this island has led many lives, celebrating triumphs and enduring defeats, only to rise again.