Trikkala is a city in a fertile valley in northwest Thessaly. Trikkala was an important transit point, with roads running west across the Pindos Mountains to Epirus and north to Grevena and Macedonia. Prokopios names "Trika" among the Thessalian poleis whose walls were repaired by Justinian I. From the 4th century onward, the city was a suffragan bishopric of Larissa. The first known bishop, Heliodoros, was thought to be the author of the Aethiopica. The old name Trikka survived in several anachronistic texts, while Trikkala appears first in Kekaumenos, who speaks of Trikalitan Vlachs. Anna Komnene cites to Trikala as a geographic name without defining the character of the site. Al-Idrisi described Trikkala as an important agrarian center with abundant vineyards and gardens. In Alexios III's charter of 1198 for Venice, Trikkala is mentioned along with other Thessalian cities. Its political role before 1204 is almost unknown: in 1082/3 Trikkala was for a short time captured by the Normans. It seems not to have been occupied by the Crusaders after 1204 but was controlled by Epirus.

After the victory at Pelagonia in 1259, John Palaiologos, Michael VIII's brother, reached Neopatras and "Trikke" and took them without resistance. In the 14th century (until 1332/3) Trikkala formed the center of the independent "fief" of Stephen Gabrielopoulos; after his death Trikkala fell under the control of John Orsini of Epiros, then of Byzantium: a chrysobull of Andronikos III of March 1336 rewards the monks of the Zablantion monastery near Trikkala for their help in transferring the city to the emperor. The Serbs conquered Thessaly in 1348, and Dugan's general Preljub governed it from Trikkala. In 1359 Symeon Uros established his court in Trikkala, where he imitated the ritual of Constantinople. Trikkala was occupied by the Ottomans in 1393. In the 14th century the bishopric of Trikkala gained increasing control over Meteora.

The fortifications on the acropolis are mostly of Turkish date, but traces of the Justinianic repairs have been identified on the south side. A floor mosaic on the hill of Prophetis Elias is from the narthex of a basilica, probably of the 5th century, and the ruins of a church, presumably of Byzantine date, are on the acropolis. The Church of St. Stephen contains an inscription naming Symeon Urog and the Despoina Anna. Many small churches, especially of the 12th-13th century, can be found in the villages around Trikkala.

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