The village of Massignano, adjacent to the territory of Cupra Marittima, is situated at 255 metres above sea level and has very ancient origins. It may have been founded in pre-Roman times by the Sabines or, more probably, was a suburb of Roman Cupra Marittima that later achieved independence.

This theory is corroborated by many archaeological finds from the Roman period, including pottery and metal artefacts, an aqueduct, burial caves, and the foundations of several Roman villas.

In the Middle Ages, Massignano remained independent until 1258 when it was taken by Fermo. In 1334 it was also pillaged by Rinaldo da Monteverde, the tyrant of Fermo, and from that moment its territory was contended  by Fermo and Ascoli Piceno until 1532, the year in which the army of Ascoli captured Massignano and it fell under papal rule until the French occupation in 1797.

Visitors to Massignano today may visit the parish museum of sacred art, and neither should they miss Piceno’s oldest food fair on 14 August, the Sagra delle Frittelle!