It stands thirteen kilometers from Macerata and is listed among the most beautiful villages in Italy. In a hilly position, Montelupone boasts an extraordinarily well preserved historic center and the village is characterized by castle walls, four entrance doors - which in the past were closed at sunset and reopened at dawn - and the original stone paving preserved until today. The walls run along the perimeter of the old town for about a kilometer in length and the towers are of two types: a rectangular plan and pentagonal, the latter as evidence of the Malatesta domination. In the center of the village is the fourteenth-century Palazzetto del Podestà - or dei Priori - with the civic tower and a five arched portico surmounted by as many ogival mullioned windows placed in the main hall on the main floor, which houses a sixteenth century devotional fresco. On the main floor there is the Civic Art Gallery, to be visited together with the Museum of Ancient Arts and Crafts, which is located in the basement of the Palazzo Comunale. Nineteenth century, the town hall houses the Teatro Storico Nicola Degli Angeli, in neoclassical style with Palladian influences while Palazzo Emiliani holds a frieze by the painter Biagio Biagetti, depicting the "Four Seasons" interpreted through the vegetative cycle of wheat. Of great value is the church of St. Francis, erected by the Franciscan Brotherhood in the second half of the thirteenth century and then remodeled in the late Baroque, containing an eighteenth-century wooden choir, four statues of theological virtues made of stucco in 1752 and an organ of the 1753. On its high altar there was the Madonna del latte by Antonio da Faenza - 1525 - now housed inside the collegiate church, which also houses the Chapel of Our Lady of Sorrows, repainted by Cesare Peruzzi between 1934 and 1941. Icon of art in Montelupone is also the Church of S. Chiara, seat of the ancient convent of the Clarisse and erected between the fifteenth and eighteenth centuries, which preserves inlaid doors in 1796 by Cristoforo Casari and the large canvas of the Annunciation of the Virgin, copy of the eighteenth century Barocci.