La Pieve di San Gregorio Magno was built on the shortest and easiest route connecting Città di Castello to Gubbio.
It is located on the pass that leads from the wide Tiber valley into the narrow Carpina valley, where the road continues towards Bagnolo and from there reaches Gubbio. The Castel Vecchio, from which the village of Montone originated, was located on the hill that controlled the pass.
The foundation of the Pieve di San Giovanni Battista and San Gregorio Magno in Montone, can be quite accurately traced back to the 9th-10th century.
Since then, the diocese of Città di Castello has been dotted with a number of parish churches, located on the main roads connecting the countryside to the city. These were places where faith was spread, and where baptism for the rural population took place as well as providing resting places for travellers and pilgrims.
Since 1100, there have been records of the “hospitium” attached to the parish church, which was financially supported by the bishopric and later also by the community.
Between 1304 and 1306, Bishop Ugolino Gualterotti moved his seat to the parish church of Montone, as the Ghibelline faction which opposed him held power in Città di Castello. He convened a diocesan synod there in 1305, but it was deserted by the canons of Città di Castello cathedral. From this period onwards, the Pieve di San Gregorio was endowed with a college of canons who in the 16th century, moved with the archpriest to the church of Santa Maria in the town.
The ancient church is Romanesque in style, and has three naves divided by large arches resting on strong brick pillars. The central nave ends in a semi-circular apse.
Two of the original loopholes that provided light to the hall are visible from the outside, as well as the small single-lancet window of the apse, which was filled in during the 16th century to make way for the altarpiece.
At the end of the three naves are three altars: the main altar consists of a tabernacle with large wooden doors. The altar was dedicated to the Holy Cross, and contained wooden statues that are now kept in the municipal art gallery.
On either side of the high altar are two 15th-century stone tabernacles, that were transferred to the parish church from the church of San Francesco at an unknown date.
It must have been completely covered in frescoes but many of the works that adorned the church were lost as a result of the frequent whitewashing ordered during pastoral visits. This was necessary to ensure hygiene in a church that was the site of numerous burials. Some votive frescoes from the 15th and 16th centuries survive, as well as a Trinity on the counter-façade next to the entrance door.
Under the right aisle, a niche resting on a large stone basin built into the wall, suggests the location of the ancient baptismal font that the parish church must have had since its origins.