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Ponte del Diavolo, meaning 'Devil's Bridge', stands majestically over River Chienti in the territory of Tolentino. It is a fine engineering work originally built in the 13th century by Mastro Bentivegna. It is characterized by five arches and a quadrangular crenelated tower, enriched by a votive niche added in 1524. According to popular belief, there was a time when the people of Tolentino didn't have a bridge to cross the river. The Devil promised to single-handedly build one in a single night in exchange for the first soul that had crossed the bridge. Fortunately Saint Nicholas, the patron saint of Tolentino, had the idea of letting a dog cross the imposing bridge before anyone else. The Devil was then denied the human soul he wanted, while the whole city and the saint mocked him.
The bridge was partially destroyed during the German bombing of WWII but the thanks to the effort of the community it was rebuilt in its original form; also the bridge's door, where the city walls of Tolentino begin, is still intact.