The town's name probably derives from the name of a noble Lombard family "Lupone". It is a small town in the province of Macerata, surrounded by well-preserved medieval fortified walls which run for about a kilometer along the perimeter of the historic center, with large gate entrances, pentagonal and rectangular watch towers, a beautiful square and several elegant buildings . The town is famous not only for the production of artichokes and honey, but also for its appreciated olive oils and fine wines.
The discovery of a necropolis in the Piceno area shows that the area was inhabited since the VI century B.C. In the later centuries the town submitted the domain of the Papal States and the Bishop of Fermo. In the XII century. Montelupone had already achieved a certain importance and since the second half of the XIII century, the government was ceded between various local noble families (Percival Doria, Mainetti, Chiavelli, Brancaleone). From the earliest years of the XV century and for almost thirty years, the town was incorporated into the territory of the Malatesta of Rimini and submitted a period of development, until it was conquered by the Sforza. Finally, in the XVI century, under the patronage of Pope Sixtus V, it enjoyed a period of peace and flourished economically.
- the XIII century Church of San Francesco, that thanks to a following restoration, acquired a typical late Baroque style and inside preserves an XVIII century wooden choir and four stucco statues of the same period, as well as an organ of 1753;
- the IX century Romanesque-style Church of San Firmano, which features a three nave plan. It houses a XVI century terracotta statue of Della Robbia and a remarkable wooden crucifix;
- the XV century Church of Santa Chiara, which features remarkable XVIII century carved doors by the artist Casari and a large painting of the Annunciation;
- the XV century Church of the Pietà;
- Palazzo del Podestà or of the Priori, which is a XIV century rectangular shaped building with an arcade on the lower level and ogival mullioned windows on the higher one. The building is flanked by the Civic Tower with battlements and brackets. Inside it preserves a valuable XVI century fresco and houses the Civic Art Gallery;
- the Town Hall, built in the XIX century on the remains of an earlier medieval building and features a Neoclassical portico. Inside, the building features the Theatre Nicola degli Angeli, which preserves a superb series of late XIX century ceiling paintings by the artist Ferri;
- the XVIII century Palazzo Narcisi;
- Palazzo-Tomassini Barbarossa;
- Palazzo Chigi-De Santis;
- Palazzo Calcaterra;
- Palazzo Tomassini;
- the Medieval Gates;
- the Civic Art Gallery, which preserves Piceno and Roman archaeological finds, several contemporary and otherwise artworks by local and foreign artists;
- the Museum of Arts and Crafts.