Montescaglioso, known in ancient times as Civitas Severiana (from Alexander Severus who fortified and dominated the center), the country took the name of Mons Cabeosus probably derived from the numerous caves exist in the area. It was originally a Byzantine fortress, only to see the succession of different feudal families.
Montescaglioso had its initial development around the Abbey of St. Michael the Archangel (1079), rich in beautiful frescoes. Interesting is the mother church of the fifteenth century. dedicated to SS. Apostles Peter and Paul in whose interior contains many paintings of the Venetian school.
Noteworthy are also the church of Santo Stefano with pre-Renaissance portal and the church of the Madonna delle Grazie in Romanesque style.