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Ancient fortified town built by the Sienese to protect the Ombrone valley and the access to the hills of Siena. The medieval walls are perfectly preserved and the apse of the church of St. Michael Archangel houses beautiful frescoes by Biagio di Goro Ghezzi.
The "terra murata" or "walled earth" of Paganico was an important factor for the Sienese since it stood as a stronghold within the valley of the Ombrone and formed an outpost amongst the hills which circled the south of Siena. It was therefore created as a new settlement that would serve as a lookout post for the Republic of Siena over the Maremma and well as an outlet to the sea.
The Sienese attached great importance to the birth of this town, also called Castelfranco or Borgo-franco, because of the taxes that were imposed over a period of ten years. This is evidence of the demands made on neighbouring Boroughs in favour of the building of Paganico, and the incentives that were offered to those who decided to settle in the town. Patches of land were distributed for the building of houses, and the Borough of Civitella and the castles of Campagnatico, Sasso, Gello, Monteverdi, Casenovole and Montecodano were ordered to build kilns for the preparation of the cement that would be needed during the building.
Construction of the walls and entranceways began in 1295, and orders were given to recruit men to complete the building of the church. Paganico must therefore have been a very active centre. From 1273 there was a weekly market, and in September there was a grand three-day festival dedicated to Sant'Angelo, which attracted merchants, not only from the surrounding area but also from Siena. This tradition is still preserved to this day, with the village festival organized around the feast of Saint Michael the Archangel.
The fortifications were completed in 1335 at a great financial cost, evidence of the importance the Sienese attached to the town in its role as an outpost for the Maremma and for access to the sea; in particular to the port of Telamone which the Republic had purchased in 1303 from the abbey of San Salvatore on Monte Amiata.
Following the fall of the Sienese Republic in 1555, Paganico fell foul of both sword and fire by imperial troops. The town was partly destroyed and its inhabitants massacred. The region was then annexed to the Grand Duke of Tuscany, who in 1602 was made Marquis by Prince Antonio dei Medici, putative son of Francesco I. The height of the bridge house, or quarterdeck, on the town walls indicates that this was the lodging place of the Marquis of Paganico.
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