The hill upon which Montalcino sits has been settled probably since Etruscan times. Its first mention in historical documents in 814 AD suggests there was a church here in the 9th century, most likely built by monks who were associated with the nearby Abbey of Sant'Antimo. The population grew suddenly in the middle of the tenth century when people fleeing the nearby town of Roselle took up residence in the town.
The town takes its name from a variety of oak tree that once covered the terrain. The very high site of the town offers stunning views over the Asso, Ombrone and Arbia valleys of Tuscany, dotted with silvery olive orchards, vineyards, fields and villages. The lower slopes of the Montalcino hill itself are dominated by highly productive vines and olive orchards.
During medieval times the city was known for its tanneries and for the shoes and other leather goods that were made from the high quality leathers that were produced there. As time went by, many medieval hill towns, including Montalcino, went into serious economic decline.
Like many of the medieval towns of Tuscany, Montalcino experienced long periods of peace and often enjoyed a measure of prosperity. This peace and prosperity was, however, interrupted by a number of extremely violent episodes.
During the late Middle Ages it was an independent commune with considerable importance owing to its location on the old Via Francigena, the main road between France and Rome, but increasingly Montalcino came under the sway of the larger and more aggressive city of Siena.
As a satellite of Siena since the Battle of Montaperti in 1260, Montalcino was deeply involved and affected by the conflicts in which Siena became embroiled, particularly in those with the city of Florence in the 14th and 15th centuries, and like many other cities in central and northern Italy, the town was also caught up in the internecine wars between the Ghibellines (supporters of the Holy Roman Empire)
