The first recorded mention of Montegridolfo dates back to 1148, but it was already inhabited during the Roman period and the early Middle Ages.
Settlements in the hills began to develop from the 10th century, life in the valleys being rather dangerous. Montegridolfo was on the border between the lands of the Malatesta (of Rimini) and the Montefeltro (of Urbino), and clashes were frequent. In 1233 Montegridolfo pledged loyalty to the Malatesta, provoking the hostility of the Montefeltro, which culminated in the attack that flattened the village in 1336.
The settlement was rebuilt with tall, strong new walls within a year. The burg yo-yoed between Montefeltro and Malatesta control until it was acquired by Cesare Borgia in 1502, before returning to the Malatesta again, being taken by the Venetians in 1504 and finally being absorbed into the Papal States in 1509.
Montegridolfo then experienced centuries of hard-earned peace and tranquillity until World War II broke out. From October 1943 to August 1944, the area was laid waste by bitter fighting along the Gothic Line between German and Allied troops.
The village was severely damaged and remained so until the late ’80s, when several state bodies and private investors came to the rescue, including the stylist Alberta Ferretti.