The name Cupramontana comes from Cupra, the goddess of fertility worshipped by pre-Roman population of Piceni. It then became an important Roman Municipality. In the Lombard period it was part of the Duchy of Spoleto-Camerino, thus changing its name into Massaccio. Located in the heart of the Marche region, 505 metres above sea level, the country is an ideal destination for holidays in contact with nature and for enogastronomic and cultural tourism. Cupramontana is also the capital of the Verdicchio dei Castelli di Jesi wine, one of the most important Italian white wines, and the birthplace of Luigi Bartolini, a great twentieth-century engraver and author of the novel "Bicycle Thieves", which inspired Vittorio de Sica for its movie of the same name. Among the historical places are to be mentioned: the Abbey of Beato (Blessed) Angelo, the Church of Santa Maria della Misericordia, the church of San Giacomo della Romita, the Church of San Leonardo and the Church of San Lorenzo. Near Cupramontana is the Hermitage of the Caves - also known as Hermitage of the White Friars from the white robe worn by Camaldolesi who lived there for more than four centuries. 
Not to be missed is the wine label's International Museum, which houses an original collection of labels for bottles of wine from all over the world. Next to the historical collection, with rare pieces from the late nineteenth century, the contemporary art collection and selection is very rich, with hundreds of sketches inspired by wine made by famous Italian and foreign artists. The Museum is located in the caves of the former St. Catherine's Monastery: it is a new exhibition area (Museums in Cave), which includes "The Taste Route", a journey through the flavors, traditions and local companies and "Enocupra", a wine bar equipped for tasting and catering. The Museums in Cave also houses "Horto de i Semplici", a space that, since the origin has always been the monastic vegetable garden. In the territory of Cupramontana is the "Network nodes of the Castles of Verdicchio ", a network of several walking and cycling routes that are connected through numbered nodes (usually road intersections). Using a map of the network, you can choose your own hike or bike tour, planning a path from node to node.The most important festival that takes place throughout the year in Cupramontana is the Sagra dell'Uva (Grape Festival), one of the oldest wine festivals in Italy.