Montecassiano is located in the Italian region of Le Marche, in the Province of Macerata.
This charming place is best known for its medieval buildings and architecture along with historic sights, which is the main tourist attraction.
Founded in the 5th century, perhaps by people fleeing from the near Roman town Ricina, Montecassiano stands on the top of a hill at 215 m above sea level, overlooking the plain traversed by the Potenza River. The ancient urban structure is still preserved: its inner small roads, like concentric circles, orderly twist until the town’s highest point, Piazza Giacomo Leopardi. You can drive along its small roads, its hills and alleys, following paths that have existed since the 15th century. The town is still surrounded by medieval walls that allow entering the centre only from its three ancient gates. It truly is one of the most beautiful Italian towns, and was awarded the Orange Flag seal of quality by the Touring Club of Italy. The village of Montecassiano is an imposing structure situated amidst the Monochhia and the Potenza River and its medieval architecture is reflected through the high walls surrounding the old town. Some of these structures were built during the 14th century which look completely different from the newer buildings found here. The urban buildings were constructed along the narrow streets that ended along the main square with the existence of the Castle of Santa Maria in Cassiano from the 11th century onwards.
Piazza Giacomo Leopardi represents the heart of the town, with the Palace of the Priori standing on its northern side. The façade of the palace is characterised by a loggia with five round-arch arcades, and three finely decorated mullioned windows in its upper part. In 1938, the battlements were renovated, and a great arch, crossing the stairway leading to the entrance of the Palace and the Collegiate Church, was built. The latter, dating back to the 15th century, has a façade with a single pitched roof and, beside it, a bell tower. The Church was built following a Cistercian gothic style, with clear references to the Chiaravalle Abbey in Fiastra, which used to have legal jurisdiction over the territory of Montecassiano in the 15th century. The Church consists of three naves sheltered by cross vaults, and houses a 18th century reproduction of the Basilica of the Holy House of Loreto; a painting by Giacomo da Recanati depicting a Madonna with Saints; and a remarkable altar by Mattia della Robbia made with glazed terracotta. The main square also hosts the 14th century Church of San Marco, now used as an exhibition and meeting room, whose interior is a nice example of local late Baroque. The piano nobile of the Compagnucci Palace, , hosts in its rooms decorated with refined Pompeii-style frescos the Civic Art Gallery, dedicated to the local painter Giacomo Buratto, active in the second half of the 15th century. The art gallery shows important works dating back to the 17th and 18th century, such as the Madonna on the throne and Saints by Giovanni Ispano (1450-1528). The Church of the Santi Filippo e Giacomo hosts the Confraternities Museum (Museo delle Confraternite), which shows, among others, a fresco depicting the Madonna of St. James, attributed to Vincenzo Pagani.