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Excavations have proved that the area of Troina was settled as early as the 7th millennium BC (a farm dating from that period, and a later necropolis). Of the Greek town (most likely known as Engyon) parts of the 4th-century-BC walls remain, while from the Roman age are baths. After the fall of the Western Roman Empire it was a Byzantine stronghold and during the Islamic period the religious and moral capital of the Greek and Christian Orthodox part of Sicily; Roger I of Sicily had in its castle (which he captured in 1061) also a start base of his conquest of the island.
During World War II, Troina was the site of a battle between the Allies and the Axis forces. The town was mostly destroyed during the six-day fighting (31 July – 6 August 1943).
In 2021 the town began selling homes for as little as one euro in an effort to lure residents and increase the population size.[4]