The history of Castel del Piano (current placename was already being used in 1198) was tied to the San Salvatore Abbey (the first documents date back to the IX and I centuries.) During the XIII century it fell under the rule of the Aldobrandeschi counts of Santa Fiora. During the XIV century, together with Arcidosso, it became part of the territory of the Siena Republic: during this period the "Statutes" were conceded (1393), the Fair showcasing merchandise and livestock, September 9th, 1402, and the first Palio historical horse races were run. The historical center was closed by boundary walls and it was accessed through two gates up till 1600: Pianese (today called Porta dell'orologio) and Castiglionese (today Porta Amiata).
The medieval center maintains a harmonic series of parallel alleys interrupted by slopes, small squares (the evocative Piazzetta degli Ortaggi) and stairways. In 1600, Porta Spennazia was built to join the current corso Nasini, through a long stairway, (born by covering the moat which surrounded the walls) to the Piana (main road of the ancient village, where various artisan workshops were set up starting in the XVI century). The modern urban expansion, determined the Hei elopment of a structure based on a system of three avenues, characterized by an open plan and interrupted by gardens and squares which run along side the medieval center.
The main squares of the town are: Piazza tonda or delle Storte, where the Palio of the contrade is held in september during celebrations to honor the Madonna delle Grazie, celebration which dates back to mid XVIII century lan ed on the Piazza del Campo di Siena model, and where a peperino obelisk dominates in the center and dates back to 1883 (the first in Italy to honor Garibaldi) and Piazza Madonna, delimited by the seventeenth century palazzo Cerboni, by the chiesa dell'Opera and by the oratory della Madonna delle Grazie.


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