Around the middle of the fifteenth century, continuous border clashes have troubled the relations between the towns of Osimo and Filottrano, until April 1466, when the Magistrate of Osimo decided for a punitive expedition: herds were captured and some nobles of Filottrano imprisoned. On the escape during the incursion, an Osimo citizen left one of his boots, which in Filottrano was accepted as a pledge of victory. To remember this fact, the youngsters, as a sign of mockery, used to wander around the country a puppet with this boot, which was finally burned after jokes and jeers.
Suspended in 1468, every year for the past 30 and more years on the first Sunday of August, the tradition is re-enacted through a race called Contest of the Boot. For the entire duration of the event there are music performances and medieval jesters, a "Junior Contest " and a "Mini Contest", a costume parade, medieval games, a battle camp, themed menus taverns, flag weavers and drummers and, finally, the burning of the Puppet by the winning Contrada. This and much more is the Contest of the Boot.