The original centre of Cantiano was founded at the beginning of the XII Century. On two high areas, the Fortress of Cantiano (356 mt.), - (then Rocca Gabrielli and today Rocca S. Ubaldo)-, and the Comatrano Fortress (360 mt.). The latter was the first to be stably occupied and had a military function of controlling and defending the roadway between Gubbio and Urbino. The ruins of a military tower are visible on the top of the hill, a tower—fortress on a quadrangular plan, originally 23.50 mt. high, demolished in 1857. The first urban centre formed around the tower, the village of Comatrano, ruled by Count Bonaccorsi, who lived in the tower, with his entire family. The vestiges of the city walls are still visible along the path that leads from Piazza Luceoli to the top of the hill. From Via dei Molini, the ruins of the St. Ubaldo Fortress are also visible. This fortress was subsequently occupied and controlled by the Counts Gabrielli di Nocciolo from Gubbio. Quadrangular towers rose along the city walls, today there remains only the Pagella Tower, privately owned, it was originally a shelter for carrier pigeons. The ruins of the Castle of the Counts Gabrielli are on the hilltop, restored by Francesco di Giorgio Martini in the years 1478 – 80, after the Montefeltro family conquered Cantiano. The castle was demolished in 1797, after being pillaged by French soldiers. Also on the hilltop, is a small church dedicated to St. Ubaldo, built on a basilical plan, with a bell tower erected in 1571.