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Castelfiorentino is a hard-working town situated in the heart of the Valdelsa valley, which lies along the river's shores from which the valley's name derives. The neighbouring cities of both Florence and Siena are 48 km away and Pisa is at 56 km. The name, Castelfiorentino, dating back to 1149, was given to Castelvecchio, which had been built on the Via Francigena, in the place of the Roman settlement of Timignano. The fortified castle, on its hillside, enclosed the parish church of San Ippolito (formerly named San Biagio before the tenth century and the time of barbaric invasions) and, with a second circle of walls, Borgo d'Elsa and Borgo Nuovo.
There were a total of five gates, along with towers, but there were only two roads which crossed in the single town square (today called Piazza del Popolo). Beginning as an estate of the Cadolingi family and then of the Counts Alberti, it was progressively acquired by the Bishop of Florence in the XIIth century. It was then to suffer the consequences of the conflicts between Church and Empire, the political factions of the Guelphs and the Ghibellines, and between Siena and the same Florence. For Florence, it was an important outpost, and thus obtained the seat of the chief magistrate, the privilege of Florence's symbolic red lily on its gonfalon, or banner, and the official integration of the name Castelfiorentino. In 1260, after the battle of Montaperti, peace was signed between the two rival cities, but Castelfiorentino was still the backdrop of battles and military raids for centuries to come; until 1521 when it suffered a hard siege and was devastated by Spanish militias. Becoming diminished in its strategic importance (despite the restorations made by Cosimo I to its fortifications) its administrative importance also resulted limited, due to its dependence from the Vicariate of Certaldo.
But in 1700, with the assistance of the grand duke of Lorena, Castelfiorentino made new progress and acquired both the seats of the chief magistrate and the Chancellery, with policemen and a wider jurisdiction stretching out to Certaldo and Montaione. It accepted annexation into the Kingdom of Italy with almost unanimous plebiscite and, in 1868, it became the chief administrative seat. It was one of the first Italian municipalities to have an administration guided by the Socialist Party.

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