Everyone has heard of the Palio di Siena, but few know of the myriad events which take place in the surrounding area throughout the whole year. A cycling race is the main event in Gaiole in Chianti named: L'Eroica. It’s a historical pageant commemorating olden-day cycling which generally takes place on the first Sunday of October. The first Sunday of November a running race is held.

Moreover, there are many town festivals which, in keeping with the Christian calendar, celebrate the local patron saint. A score of events celebrate the passing seasons, animals, traditional products and historical pageants. The most noteworthy are the “Sagra del Cocomero” (Watermelon Festival) in Castellina in Chianti, “Calici di Stelle” which takes place in many town in the region, the “Sagra della Cinta Senese” (Festival of the Cinta Senese breed) in San Casciano dei Bagni and the “Festa del Barbarossa” in San Quirico d’Orcia.