Ancient Gualdo Tadino (PG) has been destroyed and rebuilt many times, the third time in 1237 after a devastating fire.
Monuments of significance include the recently restored hilltop Rocca Flea, an example of 12th century military architecture, rebuilt by the Holy Roman Emperor Frederick II in 1247 and today the setting for the Civic Museum. Religious buildings include the Cathedral of St. Benedict (13th century) whose Romanesque-Gothic façade features a rose window with a double row of columns; the Church of Santa Maria dei Raccomandati (14th century) which houses a triptych of the Madonna and Child, Saints Sebastian and Roch by Matteo da Gualdo; and the Church of St. Francis consecrated in 1315. On the main square, the Palazzo Comunale has an 18th century noble façade while the 13th century Torre Civica is all that remains of the Palazzo del Podestà, engulfed by buildings from later ages.
The territory of Gualdo Tadino has a wealth of historical, artistic and religious monuments: the ancient Church of St. Facondino whose imposing bell tower was repurposed from an even older tower; the Church of St. John the Baptist in Grello with frescoes by Matteo da Gualdo; the Church of Santa Maria del Soccorso in Rigali; the ruins of the ancient Castle of Poggio Sant'Ercolano; the Romanesque Church of Santa Maria, near the fortified borgo of Pieve di Compresseto, preserves various frescoes, some attributed to the school of Matteo da Gualdo; all that remains of the Castle of St. Pellegrino, once a checkpoint on via Flaminia and the road to Gubbio, is an imposing tower; and the Parish Church of Caprara with frescoes by Matteo da Gualdo.
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