During the Middle Ages, various fortifications were built in the mountains of Spoleto, including the Castle of Pupaggi, which over the centuries evolved into a sort of fortified village due to its geographical location. Noteworthy are the characteristic semi-underground structures dating back to the 11th century, which have been fully restored, showcasing their unshaped stone vaults. The castle also played a significant role in more recent times as a hunting residence, particularly for wood pigeon hunts. Due to its historical and architectural significance, it has been placed under the protection of the Ministry of Cultural Heritage and Activities.

Amidst tales of love and ancient rivalries arose the legend of the Bella Pupa (the Beautiful Maiden), a young girl from the castle. Fierce battles were waged by noble feudal lords from neighboring areas to win the hand of the beautiful maiden. When weapons triumphed over love, the people of Pupaggi sheltered the Pupa’s true love in the high tower of the castle. The bloody conflicts, blending myth and legend, are still recounted by the old shepherds of the region. From this story, the name Pupaggi originated, in memory of the noble and beautiful Pupa.