The Castle of Volpaia was first built in around the tenth century along the border between Florence and Siena. Given its position as a watch tower, located on the top of a hill overlooking the Pesa Valley and along the line of the Chianti Hills running from Montegrossi towards Panzano, it must certainly have been of great defensive importance. It probably contained some of the people who lived around the nearby Parish Church of Santa Maria Novella. The first authenticated document referring to the presence of this castle is dated 1172 and was drawn up at Cintoia. It certifies that the two brothers, Franculus and Galfredus from Cintoia, obtain a loan by mortgaging their possessions located in the “curte et nel Castello di Volpaio”. When the city of Florence organised its territory into the famous independent administrations called the “Leagues” in 1250, Volpaia was included in the “Terziere di Radda” of the “Chianti League”. Of course, Volpaia suffered the consequence of the centuries-old dispute between Florence and Siena several times. The most tangible signs of these events were left by the mercenary, Alberico da Barbiano, during the war between the Republic of Florence and the Visconti and also during the disastrous Aragonese invasions between 1452 and 1478. Following the fall of the Republic of Siena in the mid sixteenth century, the castle of Volpaia no longer had a military function. 
The fortified town has today lost a part of its old walls, but it has retained the beautiful keep in the middle of a pleasant square and, especially, a large number of medieval houses that, suitably restored and preserved, give this place a special beauty. The old walls also contained the old Church of Volpaia which can still be seen today, even though it was deconsecrated in the fourteenth century when the new church was built. But the most beautiful religious building of Volpaia is the fifteenth century Commendam of S.Eufrosino.Until 1932 (when it was deconsecrated), it contained a large altar piece by Cosimo Rosselli which is now in the National Renaissance Study Centre of Florence.(Portions of this article first appeared in "Toscana & Chianti News")
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