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Of all the many villages in the Chianti Classico region, Castellina probably offers the most abundant evidence of Etruscan presence going back to the 7th century B.C. Important archaeological excavations have uncovered an entire series of Etruscan villages and hamlets along an ancient road providing links to the great maritime cities of Etruria, the markets in the north, and reaching as far as the Adriatic Sea as a gateway for trading with the East.
Of particular interest is the imposing burial mound of Monte Calvario, just outside of Castellina. Composed of four vaults, facing respecitvely north, south, east and west, it is one of the most impressive monuments in the region. A small chapel once stood at the summit of the mountain, commemorating the last station of the Cross and giving the mountain its name.
On the ancient road to Siena in the south, further archaeological finds were made: a small necropolis consisting of five separate tombs and several death chambers. They contained artifacts and burial objects suggesting the existence of rich families of noble birth who lived in this region during the 6th century B.C., a period considered the time of the most splendid artistic expression in Etruscan history. Traces of the once powerful Etruscan settlement of Castellina indicate its sudden tragic destruction, possibly by fire, around the 1st century B.C.
After a long period of relative peace, Castellina found itself at the center of fierce battles between the cities of Florence and Siena for dominance of the region. Consequently, it played an important military role in the defense of all the roads leading in and out of the entire valley of the Elsa river. Majestic fortresses, castles and defense walls were constructed throughout the area, most of them in ruins today. At one time, a fortress surrounded the entire town with massive walls and imposing towers which could only be entered by two gates on opposite sides. Today, most of the walls still stand but the gates no longer remain. The medieval keep now serves as the town hall and museum. On display are Etruscan ointment jars made in Vulci, painted vases with typical black ornamentation, pottery made of vitreous paste, and parts of iron and bronze weapons. Within the building is an inviting courtyard with an old well, and the top floor windows offer a lovely view over the town and the surrounding Chianti countryside.
In the town's small church of San Salvatore one can find a 15th century Renaissance ciborium and a wooden Renaissance statue of St. Barnabas, the town's former patron saint. The Church's oldest treasure is a well-preserved fresco of the Madonna attributed to Bicci di Lorenzo (1373-1452). Behind the altar hangs a 17th century Tuscan crucifix. Other noteworthy items include a 17th century painting of the Annunciation and a wooden Renaissance urn donated by the Ugolini family in the 18th century. It contains the ashes of San Fausto, the town's current patron saint. The three Church bells are also of 18th century origin.
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