The patronal feast of Montescaglioso, from 18 to 20 August, is tied to the cult of two patrons: Saint Roch and Maria Santissima Assunta. On the morning of the 20th, a long procession winds through the town; in the evening, seven horses pull the triumphal cart through its streets.
Montescaglioso's calendar also has the night of the Cucibocca, on 5 January: figures parade dressed in a long cloak, with a beard, a hat and a chain at their feet, whose task is to frighten children who have not behaved well. The carnival, instead, is documented from at least 1638.