The Palio di Castel del Piano is a race with historical and religious origins which is steeped in medieval custom and tradition. It was originally conceived in order to mock enemies enclosed within the town’s defensive walls, or pay homage to the Virgin Mary on one of the dates associated with the worship of the Mother of Christ. The Palio di Castel del Piano is closely linked to the Sienese domination of the region, especially the 1402 concession to hold a goods and livestock fair on 9th September, the day after the festival of the Madonna del Fileremo. The first races at the fair took place between animal owners and cart drivers, who came to the town for the celebrations and the market. One story holds that, in 1430, four Sienese mercenaries, who were under threat of attack from the Aldobrandeschi counts’ men, were saved thanks to the presence of an icon depicting Our Lady of Grace, painted by the Sienese painter Sano di Pietro. The four soldiers, who had miraculously escaped ambush, stole the sacred image that had warned them of the impending attack and took it to the Sanctuary of Our Lady of Grace. The Palio was founded the following year and has taken place ever since. In its present form, the race involves competitors from the town’s four contradas (city districts): Monumento, Poggio, Borgo, and Le Storte.