Montelupone

Montelupone is a hilltop village in the province of Macerata, about 13 km from the city of Macerata, with views toward the Adriatic coast. Its origins are traced either to a Longobard family, the Luponi, or to descendants of the Roman Lippia family; a necropolis discovered in 1926 provides evidence of settlement here as far back as the 6th century BC. In the Middle Ages the fief belonged to the Grimaldi family, who in 980 commissioned the nearby Benedictine Abbey of San Firmano. The historic centre developed in a circular plan within roughly a kilometre of still-largely-intact medieval walls, dated to around 1400, with four surviving gates — Porta del Trebbio, Porta Ulpiana (San Michele), Porta di Santo Stefano (Marina), and Porta del Cassero (del Castello). Montelupone is recognized as one of Italy's most beautiful villages ("I Borghi più Belli d'Italia") and holds the Orange Flag quality designation.

The historic centre sits within the old walls atop the hill and is small enough to explore entirely on foot.

Montelupone's medieval walls, roughly a kilometre in circuit and dating to around 1400, still ring the historic centre with four surviving gates. Inside, the Palazzo del Podestà houses the civic art gallery, the 19th-century Teatro Nicola Degli Angeli is the town's historic theatre, and the Monumental Church of San Francesco is a notable religious building. A short distance outside town, the Romanesque Abbey of San Firmano, commissioned by the Grimaldi family around 980 and rebuilt in its current form around 1200, is another sight worth the trip. The town also has a Historical Photography Museum and an Arts and Crafts Museum.