The reign of the magical prophetess Sibyl, who is said to have also predicted the birth of Frederick II. In the Middle Ages, the priestess dear to the Romans became the protagonist of the medieval chivalric literary imagination as a bewitching and seductive witch, not at all benevolent towards men. A demonic aura that grew thanks to the poems Guerrin Meschino by Andrea Barberino of 1410 and Le Paradis de la reine Sybille by Antoine de la Salle of 1420, which made the Apennine Sibyl (also known as Sibilla Picena) world-famous.
Land of mysteries and many castles disputed by lay and ecclesiastical lords fighting each other for a long time. This was the case for the famous Rinaldo di Brunforte and for the Manardi (or Mainardi) counts, who were lords of Acquacanina, Bolognola, and Amandola. Amandola also knew the dynasty of the lords of Montepassillo, who have Alberto di Smerillo as their ancestor—a sharp man who established close relationships with Barbarossa until he was given a large part of the territory of the nearby Comunanza. Alberto built his residence in Smerillo, while his descendants founded the castle of Montepassillo, the current Comunanza.
The clash between the Swabians and the Papacy became a clash of local governments: riots, sieges, fights, unions and divorces followed one another incessantly as the winning alliance among Montefortino, Amandola, and Sarnano against the troops of Manfred, son of Frederick II, in the plateau between San Ginesio and Sarnano.
The opposition to lordly powers resulted in a very peculiar system of government: the guaite, autonomous districts protected by walls, each with a prior who represented its population in the government of the community.
These included Visso, Ussita, Castelsantangelo sul Nera, Villa Sant’Antonio and the hamlets of Macereto, Aschio, and Cupi. This form of administration remained intact until the end of the 18th century.