Going up a dirt track branching off the state road S.S. 361, near the cement factory but on the opposite side of it, you can find the very old monastery of Madonna delle Macchie of Gagliole. It’s a monastery which was built in several steps starting at least from the 14th century. The complex consists of a four-sided portico faced by other monastic buildings and two churches. The oldest church is a Gothic building with pointed arch portals and cross vaults, inside of which there are several frescoes attributed to the 14th century painter Diotallevi di Angeluccio as well as other paintings, most of which are in the Diocesan museum of Camerino. They date back to the 15th century and they were painted by an anonymous artist called Maestro delle Macchie. Next to this church there’s also another one which was created by enclosing an old portico with a wall.
Also in this church there are various votive frescoes, but particularly noteworthy, in the apse wall, is a great Assumption of Mary which was painted between the 15th and 16th century drawing inspiration from the art of Signorelli.
In the original church two images of the Vergin Mary with Child and Saint were probably painted by the Master from Esanatoglia. Some traces of the Camerino School of painting are still visible in the Abbot St. Anthony between St. Jerome and St. Rocco and in the traces of the Crucifixion, of a Madonna with child and the Martyr St. Venantius. In the second church a large number and type of votive offerings can be seen, some of which were painted by Girolamo di Giovanni from Camerino: the Nursing Madonna, St. Bernardine of Siena and the abbot St. Anthony (1483).
Beside those travelling to Rome and Loreto, there were in the Macchie area other men and communities coming from neighbouring lands. Votive offerings, pilgrimages, offers to the sanctuary are other forms of popular religion fascinated by woods, hermitages and festive breaks. These images were considered to have beneficial miraculous powers. The images represent: the Vergin Mary, St. Anthony protector of animals, St. Rocco and St. Donnino, protector from leprosy and rabid dogs, St, Venantium, patron saint of Camerino and protector from falls.