Staffolo is placed on the ridge of a hilly formation overlooking a sweeping view right across the valleys of the Esino and Musone rivers. Called the “Vallesina balcony”, the borgo is well set down, nestling in a countryside of gentle, elegant hills carpeted with olive groves that cast a greeny-silver hue over the surrounding landscape.
According to ancient tradition going back to the XVI century, the name Staffolo is linked to the wine production which has always characterised this area.
According to some sources, the name derives from the Greek “Staphile” “Bunch of Grapes”; others, however, refer to the topographical conformation of its historic centre protected by walls, which bring to mind a horse stirrup.
The more credible historic hypothesis however, places the settlement of Staffolo as a pre-existing Roman military garrison which developed into a fortified settlement taking the name “Staffil” (border stake) or (in a wide sense “crossroad”), during the Longobard domination around the VI-VII century.
The first sure historic mention of Ancient “Stafuli” dates back to the year 1078 when the habitat was annexed to the possessions of the Cima family who held it for about two centuries.
Becoming a free commune in the XII century, the centre had to submit for only two brief periods to the supremacy of nearby Jesi. Towards the middle of the XIV century, the commune participated in the disastrous politics of Giovanni Visconti, Duke of Milan and was obliged to submit to heavy reprisals with sackings and sieges carried out by the troops of the Sarzana league led by Fra Moriace (1354) who razed to the ground both Castle and walls. The walls were then restored on the wishes of Cardinal Albornoz and Staffolo tried to again consolidate its own communal authority; however in 1433 it was occupied by Francesco Sforza who attempted to establish his dominion in the Marca Pontificia. After new pillaging by Francesco Maria della Rovere and his band, during the war against the Medici family to take back the Dukedom of Urbino (1517), Staffolo returned to the sphere of the Pontifical State putting itself under the protection of the city of Jesi, whose historic destiny it shared until the Napoleonic domination. In 1861 the borgo was included in the Reign of Italy as a commune of the province of Ancona. Repeatedly devastated and then rebuilt in the Middle Ages, Staffolo is still today enclosed by the Medieval walls and rich in historic evidence.
Annually since 1966 in the third week of September, the gastronomic “Verdicchio d'Oro” national award and “Staffolo city award” ceremonies are held. This important event, one of the foremost on an international level, is entirely devoted to Verdicchio wine; it is a round table on the famous wine in the local gastronomic setting, the prize-giving ceremony takes place in the memorable background of the Collegiate of St. Francesco, where illustrious names linked to Verdicchio and Italian gastronomy awarded prizes.
Since 1995 in concurrence with “Verdicchio d'Oro” the “Staffolo city prize” is awarded annually to distinguished personages in recognition of their economic activity in the Region.

Monuments