It has been held for decades on the first Sunday of the month of October, and the preceding Thursday, Friday and Saturday. It celebrates not only the grape harvest but also the fertility of the land, particularly important in this area rich in vineyards planted with Verdicchio vines. The Sagra Dell’Uva derives from a rich and ancient heritage, encompassing traditions, culture, economy and agriculture of the area, and has become a party for the inhabitants and also draws thousands of people to Cupramontana for the days of the festival.

The characteristic elements of country folk are evident with a warm welcome: the traditional dances, including the "Saltarello" (a local dance) performed by local folk groups, songs that were sung in the fields during harvest time accompanied on various instruments including accordions and concertinas. Il Palio Del Verdicchio is an annual competition held on the Saturday afternoon where teams must tread grapes with their feet, just as was done in past centuries. The highlight of the festival, held on the Sunday afternoon, is the Parade of Floats. Each parish (or quarter) of the town and the surrounding areas have their own decorated wagon which follows a subject of wine and the traditions of winemaking. Each year the theme varies, as affected by the current environment, politics, social or historical events – the outcome is creative and entertaining.