Gualdo has a long history and was originally an Umbrian village known as Tarsina. Conquered by the Romans in 266 BC and re-christened Tadinum, it was a station on the Via Flaminia. In 217 BC it was destroyed by Hannibal's troops. A similar defeat was inflicted on it in 47 BC by Julius Caesar and in 410 AD by Alaric's Visigoths.

In 552, the Byzantine general Narses briefly restored Italy to the empire by defeating the Ostrogoth king Totila in what is now known as the Battle of Taginae in the plain to the west at a place called Taino.

The ancient city survived that war, only to be destroyed in a later war at the instigation of the Holy Roman Emperor Otto III in 966. It was later rebuilt, only to be destroyed a second time by fire in 1237. Finally, the Emperor Frederick II ordered the city rebuilt for a third time in 1239, and it is this incarnation which survives today.

Main sights

• Rocca Flea, a 12th-century castle which is now the main monument of the town.
• Church of St. Francis (13th century), housing frescoes by Matteo da Gualdo.
• Gualdo Tadino Cathedral (Church of St. Benedict), with an external fountain attributed to Antonio da Sangallo the Elder (16th century).