Established by the free Commune of Gubbio in the twelfth century, it played a leading strategic role in the defence and control of the most impassable and well-concealed route - albeit the shortest one - between Umbria and the Adriatic coast. The area was inhabited starting in the Iron Age , and even before the settlement established by Gubbio, there existed a site known as "Serra", which means "closed place", with a church dedicated to Serra Sant'Abbondio. It originally came under the monastery of Classe, then under Fonte Avellana and, lastly, the Abbey of Nonantola
In 1384, Serra Sant'Abbondio became part of the Duchy of Urbino and thus in 1481, Duke Frederick of Montefeltro appointed the Sienese architect Francesco di Giorgio Martini to build a fortress to defend the valley, which the architect described in detail in one of his manuscripts. Nothing remains of the fortress, which was destroyed by Duke Guidobaldo to keep it from falling into the hands of Cesare Borgia. The layout of the town has maintained the structure typical of the old medieval hamlet, with two gates of the original four gates leading into the town: Porta Santa, with a tower, and the thirteenth-century Porta di Macione. The two streets that run parallel to the main street frame the stone buildings marked by their simple and linear architecture. Be sure to see: the Hermitage of Fonte Avellana, the Crypt of San Biagio, the Chiesetta della Canale, the medieval walls of the historic centre, Porta Santa, Porta di Macione.