The first records of an inhabited settlement in Cannara area go back to around the Ist century B.C. This is probably the date of the town's foundation, but one believes that the settlement which the Romans called "Castrum Canarii", became a real town only after the barbaric invasions in Italy.

The toponymical analysis reminds us that, when Valerio Ranieri built the castle, the area was known for its swamps and marshes abbundantly covered by canes. Fought over between the end of the of the 13th century and the middle of the 14th century by the Guelfs and the Ghibellins, it was first subjected to the rule of the Duchy of Spoleto and afterwards, after it had been a strong-hold of the Breton soldiers around 1400, to that of the Papal State.