La sua storia affonda le radici nell'epoca romana e poi nel IV secolo, quando lo scalpellino Leone vi fonda il primo luogo di culto cristiano locale, ma è tra la metà del XIV e la metà del XV secolo che la fortezza vive la sua epoca di maggiore contesa, tra le famiglie dei Malatesta e dei Montefeltro, e poi nel 1517 quando Antonio Ricasoli, a capo delle truppe fiorentine dei Medici, guida un'incredibile impresa bellica e riesce a espugnare la fortezza.
Ma la vicenda storica più celebre legata al Castello di San Leo è sicuramente quella del Conte Alessandro Cagliostro, nome d'arte dell'alchimista e truffatore Giuseppe Balsamo, qui imprigionato tra il 1791 e il 1795 per volere del Sant'Uffizio con l'accusa di eresia, massoneria e attività di sedizione.
A narrarcela è Carlo Lucarelli nel sesto episodio di "Giallo in Castello", il podcast di Carlo Lucarelli e Regione Emilia-Romagna dedicato ai Castelli dell'Emilia-Romagna.
Il progetto è co-finanziato dai Fondi europei della Regione Emilia-Romagna – Por Fesr 2014-2020
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