Rocca di Pierle, Ruined medieval castle in Cortona, Italy

Rocca di Pierle is a medieval fortress located on high ground between Tuscany and Umbria with tall defensive walls and several square towers at key points. The structure includes a residential keep, a main gate with drawbridge mechanics, and other fortifications arranged to control the surrounding territory.

Built in the 11th century, the castle passed from the Marquises of Monte Santa Maria, who allied with Cortona around 1200, to the Perugian Oddi family in 1225, then to the Casali of Cortona in 1236 under Ranieri. Francesco I Casali had it rebuilt in 1371 on the earlier structure to a design by his son Ranieri, to defend Cortona, 16 km away, from Perugia. Florence bought it from King Ladislaus of Naples for 1,200 florins in 1411.

The castle gave its name to the hamlet of Pierle that grew around it, and the houses of the borgo were built with stone salvaged from the rocca itself. The wives of the lords of Pierle came from families such as the Ubaldini, Antelminelli, Da Varano, Da Polenta, Brancaleoni di Piobbico and Salimbeni. A garrison of a castellan paid 40 lire a month, five crossbowmen and four armed men watched over the castle and the noble apartments.

The ruins stand in the hamlet of Pierle, near Mercatale in the municipality of Cortona, about 16 km from Cortona. The enclosure wall runs 220 m and reaches 5 to 8 m in height; two of the four towers remain, along with the drawbridge groove and loopholes. The site covers 3,500 m² and is private property, so the interior is not open; the walls and towers are seen from outside.

The fortress was the site of a major political crisis in 1387 when roughly 60 conspirators were executed there. This event revealed deep tensions between the rival powers of Cortona and Perugia as they competed for control of the region.