The first settlements in the area date from the 7th century BC, belonging to the Apuli Italic tribe. The original nucleus of Montescaglioso grew substantially in the following centuries, thanks to trade with the nearby Greek town of Metaponto. When the latter decayed in Roman times, Montescaglioso further increased in importance. Archaeological findings include a large tuff wall dating from the 3rd century BC.
After the decline of the Western Roman Empire, Montescaglioso is mentioned first only in early medieval times. A Byzantine stronghold, it was captured by the Normans after the year 1000, and housed an important Benedictine community. Under the Angevin and Aragonese dynasties of the Kingdom of Naples, it belonged in sequence to the D'Avalos, Orsini, Loffredo, Grillo and Cattaneo feudal families.
Benedictine Abbey of San Michele Arcangelo, existing at least from 1078 and probably built in the 5th century. The Norman lord Humphrey of Hauteville and his son Rudolph made large donations to the abbey, which flourished until the 15th century. Afterwards it decayed due to numerous wars ravaging the country in those years. The Abbey Church (12th century), dedicated to St. Michael, has a notable portal and a Norman-style bell tower with mullioned windows. Renewed starting from 1590, it received a cylindrical cupola in 1650.
Mother Church (1776), rebuilt in late Baroque style over a pre-existing medieval structure. In the aisles are four canvasses by Mattia Preti. There is also a 15th-century panel of the Madonna with Child.
Church of St. Stephen (11th century)
Church of St. Lucy (11th century)
Church of Madonna della Muova (11th century) and Madonna delle Grazie (1065).
16th centuries churches of St. Roch, St. Augustin, Santa Maria del Vetrano.