In Roman times, the small village of Gallano became an important post station thanks to the Via Consolare Flaminia (220-219 BC) which in the past crossed the valley below. This artery was fundamental for the great Roman Empire because it connected Rome to Northern Italy, in particular the Via da Roma led to Rimini, the ancient city of Ariminum. Even today we can still admire in this stretch important remains of arches of the bridge called Centesimo, so called because it was located one hundredth mile from Rome.

In 1085, Gallano became the seat of an important Benedictine monastery under the name of Santo Stefano; after several incursions and attacks, during the riots that marked the Italian peninsula in the last decades of the 12th century between the Municipalities and the Emperor, the Monastery was fortified with imposing walls and bastions, so that it was transformed into a real fortress Castle. It was the great Emperor Frederick I, Barbarossa, who in 1155 established the figure of the Count of Gallano, recognizing the place's significant importance. In 1350, the Monastery was definitively abandoned, for reasons unfortunately still unclear, but it still remained in the hands of the Church. Only in 1383 did Pope Urban VI cede it to the Trinci, Lordship of the city of Foligno, who obtained the position of Visconti.

At the end of the brief Trinci era in 1439, the city returned under the direct control of the Church and remained so for several centuries to follow. During the Trinci domination, the church of San Sisto was frescoed by the famous Foligno painter Pier Antonio Mezzastris and, in 1891, one of these frescoes was removed and placed in the cathedral of Foligno, where it is still preserved today.
It is clear from the oral culture passed down from grandfather to grandson, which is very much alive in this part of Umbria, that for a long time it was a solitary place marked by the seasonal rhythms of the land and that only at the beginning of 2000 did it resume its ancient appearance.

In 2008, after almost 40 years of total abandonment of the village, a family, the Becca family, fell in love with the charm of the estate and the grandeur of the residence, deciding to take on a challenge: to bring everything back to its former splendor, transforming the site into an elegant and exclusive Charming Resort, but respecting its history. After careful recovery and restoration work, the Castle has thus returned to its ancient splendor, still preserving the original medieval structure with the annexed small patronal church dedicated to San Sisto di Gallano. In 2015, it was therefore awarded the Certificate of Commendable Participation as a deserving interpreter of the UNESCO Values in the protection and safeguard of the landscape and the environment, within the Competition 'THE FACTORY IN THE LANDSCAPE'.