Cortona, the medieval town located near the farmhouse, organizes every year in its historic centre and all over its territory a wide range of cultural, gastronomic, historical and folklore events. The best known of all historical re-enactments which takes place in town is the Giostra dell’Archidado which celebrates the wedding between the Lord of Cortona, Francesco Casali and noble Antonia dei Salimbeni di Siena. This costume event features parades, dances and the Colata dei Ceri (candle casting) which culminates, on the last Sunday of May, in a crossbow competition (the Giostra) in which the five city districts compete.

Every year between late August and the beginning of September Cortona hosts in the rooms of its 18th century Palazzo Vagnotti, the former seat of the Seminario Vescovile, the Mostra Mercato Nazionale del Mobile Antico (National Antique Fair). This attracts a host of people and highlights the cultural, artistic and environmental characteristics of the town.

Since 2012 the Cortonese summertime is also characterized by an amazing art, music, film and literature festival, the Cortona Mix Festival, which wants to convey a message of peace and culture sharing with concerts, exhibitions, conferences and meetings with important personalities of the world of literature, cinema and music.

Several places located in the vicinity of the town that may be easily reached by car offer a host of events attracting thousands of tourists and curious visitors each year. Amongst these the best known is certainly the Palio di Siena ; this is not just a historical commemoration for tourist purposes but rather a significant part of the life of the people of Siena. The Palio dates back to the mid-18th century when the horse race was run for the first time. On July 2nd and August 16th the town stops and suffers and rejoices for their own “contrada”.

Another interesting event takes place in Montepulciano on the last Sunday of August. The “Bravio delle Botti” (barrell rolling contest) is a 2Km race along the steep streets of town in which the different “contradas” compete rolling a huge barrel. During the week of the Bravio city streets come alive with the colours of the flags of the different contradas as each of these stage small shows and organize lunches and dinners and turn the whole of Montepulciano into a huge party.

The “Corsa dei Ceri” (the race of candles but actually tall wooden pillars) is without any doubt one of the oldest festivals in the world: this is definitely one of the most unique races you will ever get a chance to see. The race takes in place Gubbio on May 15th, the eve of the feast of Saint Ubaldo, who is the patron saint of the town. The Ceri is actually a 7 meter tall octagonal wooden machine topped by the statue of a Saint and fixed to a stretcher that is carried by eight people called the “ceraioli”. They are dressed in the colours of their town “contrada” and run through the streets until they reach Saint Ubaldo cathedral.