Thessalian Nymph, 4th Century BC
In northern Thessaly, you find the town of Phalanna. Livy in History of Rome 42.54 mentions Phalanna in his account of the Third Macedonian War against the Romans (171–168 BC). After four days attacking and ultimately wrecking and burning the city of Mylae, King Perseus of Macedon marched on to Phalanna, and on the following day arrived at Gyrton.
AE coin similar scale to yours of Phalanna from ~150-200 years earlier than Livy's reference. It was minted not far from the time ~352 BC when Philip II of Macedon was appointed Archon of Thessaly for life, making him head of the Thessalian armies and uniting Thessaly and Macedon. Rogers (1936) overview of copper coins of Thassaly, describes Phalanna as the daughter of Phoenix and sister to Tyros. Phalanna is said to have founded the city, and is the nymph on the coin. The male head is ambiguous, possibly Ares but Rogers also mentions a similar coin with Apollo. To me this coin looks like Apollo. An error in reverse legend with a retrograde N and although faint in the photo, the letters "ANNAIΩN" are all visible with a magnifying glass.
Thessaly, Phalanna, 380-350, Æ Trichalkon
Obv: Youthful male head right (Apollo or Ares?)
Rev: [ΦAΛ]–ANNAIΩN, head of nymph, Phalanna, right, with hair in sakkos [a hairbag made of a coarsely worked wool or linen], wearing earring and necklace
Size: 18mm, 6.04g