[3] In the Serralta territory, 10 kilometres (6 mi) north of San Severino, characteristic remains from the medium Palaeolithic and High Palaeolithic have been found whereas human presence in Pitino, located 4 kilometres (2.5 mi) north-east of the town, goes back to the medium Musterianum Palaeolithic.Metallic remains with a symbolic function were found in many areas of the communal territory, documenting the uninterrupted settlement and the existence of a complex social hierarchy of the whole prehistoric era.

At the foot of the Monte Nero there was a sacred temple, a unique one in the region, devoted to the cult of the goddess Feronia, divinity of Sabine origin to which the Liberti were consecrated.

Together with other inscriptions, this demonstrates that the town of Septempeda grew as a prefecture and was raised to the rank of Roman municipality with a strategic role in controlling the trade through an important way connecting the Adriatic Sea to Rome.

Incursions of both Germanic and Byzantine troops by the 6th century, forced the inhabitants to find shelter in near high grounds, and in particular on Monte Nero (the hill that overlooks the present day town) where existed perhaps since Roman ages, a military organization called “Castrum reale”.

The first reliable document concerning the existence of this new centre dates back to 944, year of foundation of a larger church to accommodate the faithful and the relics of Saint Severino that was placed in the hamlet of the "Castellum Severinum Sanctum".

Documents from the 11th and 12th centuries show that the Castle of San Severino was part of the diocese and the Camerino March before being transferred in 1119 to the Marquis Werner II of Spoleto, who had come from Germany to fight for the Pope against the Normans.

At the beginning of the 14th century San Severino managed to increase its domains with other castles, such as Pitino, Gagliole, Carpignano, Aliforni, Frontale and Isola, reaching the current territorial extension.

Many inhabitants had come down from Monte Nero increasing the population of the existing small village, setting up paper mills and silk, wool and clothes factories, goods exported all over the Marche.

Francesco Sforza, a condottiero owning several lands in the Marche, settled down in San Severino between 1443 and 1445, welcomed by the inhabitants who saw in him enough power to resist both the absolutisms of the local lords, and the tyranny of the Papal vicars.

This ended up with the subjugation of San Severino by the army of Papal commander Giovanni Vitelleschi, and the subsequent imprisonment of Smeduccio Smeducci in Castel Sant'Angelo.

At that time the town was troubled by the conflicts between two nobles families Caccialupi and Gentili, which divided the people into two factions and required a direct intervention of Pope Paul III that was ineffective.