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The walled town of Paganico ca be found along the SS223 near Grosseto.
The development of Paganico, and its passage from little village to walled town, is strictly connected to the beginning of the Sienese domination on this area of the Maremma, started in 1193. The fortified strongold, placed at the confluence between the rivers Ombrone and Lanzo, was constructed along the main road that from Siena, passing through S.Lorenzo a Merse and Forcole, leads to Roselle and Grosseto, giving origin to a real 'terra nuova', a settlement straight in the heart of the new southern territories of Siena.
To facilitate the economic growth, Paganico was free of fiscal impositions and taxes, so that at the time was named Castelfranco Paganico. To increase its importance in 1294 the town was made seat of an important market to destabilize the feudal economic system of the zone, controlled by the Ardengheschi family. In order to complete the elevation of its rank, since 1303 Paganico was seat of a vicariate. The damages provoked by the mercenary troops and the nasty air of the Maremma, at that time a malarial swampy region, caused, starting from the mid-13th century, the depopulation of Paganico. In 1494 the town was sacked from the troops of Carl VIII° then it passed under the Medicean control but only with the Grand-Ducal drainages, carried on in the 18th century, the area known an economic and social rebirth.
The first walled enclosure of Paganico dates back to 1278 and was destroyed in the 1328 by Castruccio Castracani. Little after, in 1334, were erected the new town walls, under the direction of the architect Lando di Pietro, the same director of the works at the New Cathedral of Siena. These walls have the shape of an irregular quadrilateral, nearly trapezoidal, with squared towers on each curtain, four massive tower at the angles, four gates placed at the extremities of the two main road that crossed the town. Remnants of the machicolations are still partially visible. A tall keep or 'mastio' [called Cassero Senese, transformed in medicean age in a residential palace], flanks of the North gate, also known as 'Porta Senese'. The North and South Gates were equipped of a small barbican, now disappeared. The eastern front of the town walls with its Gate is nowadays totaly lost, together with some part of the northern, but all the other sides still surround the town, even though in some parts damaged. Intact are the 'Porta Grossetana' (or Franca) and the Porta Senese, both endowed with the characteristic pointed arch overlapping a lowered round arch surmounted by the black and white coat of arms of Siena. Partially intact is also the Porta Ovest.
Inside the town is geometrically laid out, as all the planned settlements, with some beautiful medieval mansion with porches and, in the main square, the recently restored well and the Romanesque church of S.Michele, erected between 1296 and 1305, with two cycles of frescoes attributed to Biagio di Goro Ghezzi.