Thessaly is characterized by a high proportion of flat land and lowlands, surrounded by mountains that limit its access to the sea and isolate it from neighboring regions. This geographical feature contributed to a unique economy, where the focus was not on vine and olive cultivation, typical in other Greek regions, but rather on the production of cereals and wheat. The fertile plains also provided ample grazing land for cattle, and Thessaly became renowned for a breed of horses. These agricultural and livestock themes are reflected in the region's coinage, with the bull featured in the 5th century BC and horses appearing throughout the 4th century BC.

The chief city of Thessaly, Larissa, was named after a nymph of the same name. According to myth, Larissa was either the mother or daughter of Pelasgus, the eponymous ancestor of the Pelasgians, the earliest inhabitants of the region. The city's coinage often depicted Larissa, and one notable example is a coin featuring her portrait, which closely mimicked the famous frontal portrait of Arethusa, engraved by Kimon for a 406 BC Tetradrachm from Syracuse. This iconic design was widely admired and became a prototype for various other Greek city-states, influencing the appearance of many subsequent coins.

It has been suggested that the coinage featuring Larissa was issued to commemorate the victory of Medelos of Larissa at the Battle of Pharsalus around 395 BC, as described by Diodorus. According to the account, Medelos, the ruler of Larissa, defeated Lycophron, the tyrant of Pherae, and captured Pharsalus, selling its inhabitants as slaves. The obverse of the coin, depicting the nymph Larissa, is modeled after the famous Syracusan coin featuring Arethusa, while the reverse alludes to the economic foundations of Thessaly, emphasizing its wealth derived from agriculture, livestock, and particularly the famous breed of horses unique to the region.

THESSALY. Larissa. Ca. mid-4th century BC. AR stater or didrachm (26mm, 12.32 gm, 4h). NGC Choice AU 5/5 - 4/5, Fine Style. Head of nymph Larissa facing, turned slightly left, hair in ampyx, wearing pendant earrings and necklace / ΛΑΡΙ-Σ-ΑΙΩΝ, bridled horse prancing right on ground line. HGC 4, 409. BCD Thessaly I 306-311. BCD Thessaly II 1160.

Ex MDC Collection coins sarl, Auction 5 (14 November 2019), lot 33; Nelson Bunker Hunt Collection (Sotheby's New York, 19 June 1990), lot 93