The origin of the fortified complex goes back to the Early Middle Ages, though the only thing we know about the original fortification is that it was completely destroyed by Lucca in 1170. Rebuilt and once again besieged, after the 1371 peace treaty the small town definitively passed under Lucca, that expanded the walls and reinforced the entire fortification around 1390.
Castiglione was one of the communities in Garfagnana
that, contrarily to the majority, refused to accept the rule of Ferrara's Dukes, remaining loyal to Lucca. For this reason in 1603 and again in 1613 the town was besieged by the artillery brought from Modena: walls and rocca
were under fire for several days and long sections of the curtains were destroyed. From 1617 onwards, after the territory of Garfagnana was officially handed over to the Dukes of Este, almost two centuries of uninterrupted peace followed. The walls and the rocca of Castiglione then lost their military function and in the nineteenth century, when all unused garrisons were demobilised, the Rocca, like other fortifications in the area, was sold and became a private residence.