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The origin of Montecastrilli goes back to the time of Hannibal, who stayed there, leaving the so called "Castrillorum" which in Latin means "camps".
Before joining the Papal States, the country underwent the domination of Todi, and knew the bitter rivalry of families todine emerging 1400. Beautiful medieval village remains the structure of city walls framed by a series of crenelated towers, in which open Amerina Porta and Porta Medieval. Now independent town in 1975, today Montecastrilli includes interesting fractions of Castello dell'Aquila, Castel Todino, Farnetta, Quadrelli and Collesecco. To visit the Convent of Clarisse of 1400, in the parish church of particular interest is a wooden crucifix of the fifteenth century; near in the campaign, San Lorenzo in Nifili century. XI, a remarkable example of Romanesque-style Umbrian. Recently, were also restored two splendid paintings from the monastery of Montecastrilli, and today exposed in the church of Santa Chiara, depicting St. Nicholas of Bari and St. Bonaventure of Bagnoreggio. Both works, author unknown, date back to the first half of 1700.
 
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