The Palio dei Castelli is a re-enactment event held in Castiglione Olona, usually in the second week of July, in memory of the town’s important Renaissance past. It consists of various moments, the most heartfelt and fascinating of which is certainly the "Race of the Barrels."
Traditionally, the "Palio dei castelli" takes place over three days, from Friday to Sunday, varying between the first and second week of July. A series of events, which have remained fairly fixed over the years, take place over these three days. On Friday, the day of the inauguration of the Palio, the historical procession moves from the palace of Cardinal Branda Castiglioni, reaching the ancient church of Saints Stephen and Lawrence, the so-called Collegiate Church of Castiglione Olona, where the opening ceremony and blessing of the new Palio takes place, in the presence of civil and religious authorities. On the second day, the procession reaches the castle of Monteruzzo, where, in the presence of court musicians and palace dignitaries, the "Captain of the Palio" is invested, symbolically charged with "watching over the fairness and loyalty of the participants in the tenzone." After the handing over of the village keys, it is the Captain who kicks off the hoops race, the first of the scheduled contests. The third day, Sunday, is the most intense day for participants and spectators. In the village square, the historical theme is dramatized, with the help of professional actors, after which the procession, starting from the Castiglioni palace, goes through the whole village, touching not only the Renaissance village, but also those areas built later. Along the route, for some years now, the main attraction has been the Alba flag-wavers, who perform in games of skill that have awarded them several prizes, including internationally. The parade ends again at Monteruzzo Castle where, after dinner, the procession reassembles, awaiting the arrival of the barrels, which in the meantime have kicked off their competition. In recent years the program has been slightly modified and, to these traditional elements, others have been added, such as the great game of living chess, carried out in collaboration with the Chess Society "City of Varese," and the show, a mixture of theater and pyrotechnics, which takes place on the last evening in the natural amphitheater formed by the slope on which Monteruzzo Castle stands. The time frame in which the Palio takes place has consequently been expanded from three days to two weeks, within which the various parts of the event take place.
The barrel race represents the climax of the event. During this race eight teams, representing all the borough’s eight districts, compete, each with their own barrel, trying to roll it through the streets of the borough as fast as possible, to win the Palio. Each team is composed of five elements, who can take turns as they see fit in pushing the heavy barrels, but without lifting them off the ground and making every effort to get them to the finish line intact. Main difficulty of the race is some uphill sections that the athletes have to run, as well as the weight of the barrels. In addition, the barrels do not have the same weight, but are assigned to teams by drawing lots, leaving luck a large part in deciding the final winner.