Immersed in a pleasant landscape of soft hills rolling towards the plain, the hamlet of Montegridolfo rises like a sentry on a crest naturally dividing the Conca valley in Romagna from the Foglia valley in the Marche.
The scheme of the town, still encircled by walls and a tower equipped with a Medieval door, which provides an access to the town itself, envelopes in a castle-like style the historical centre which preserves unblemished its remarkable beauty.
The hamlet was part of a cluster of nearby castles meant to ensure protection to the seignory of the Malatesta against the neighbouring Marche territories submitted to the dukedom of Urbino.
As of yet the origin of this hamlet remains uncertain. It is certain that the previous name, Monte Lauro, most probably came from the bay-tree that used to grow conspicuously in the surrounding woodland. Whereas the current name, Montegridolfo, dates back to the XIII century at the time of the Castrum Gredulphus foundation, which took its denomination from the Gridolfi family, Guelphs from Rimini, who moved to this area during the Guelph and Ghibelline dispute.
The Montegridolfo Castrum was neither a residence nor a military settlement, but a fortified hamlet surrounded by the walls, i.e. a "cassero", characterised by a rectangular fence with a tower-door with defensive purposes, inhabited by rich artisans and farmers.
Following the Goths invasion the populations living along the coastline were forced to retreat up-country originating small protected settlements. This is an hypothesis concerning Montegridolfo’s origins of which the early settlement’s precise dating is unknown, although some would speculate on it being erected around the year 1000. The first historical record referring to the settlement dates back to the 1145, when it was listed among the possessions of the Abbey of St Peter and Paul from Rimini.
In 1233, Montegridolfo’s mayor, Pasitto, swore allegiance to the Comune of Rimini thus entering the Malatestiani possessions and engaging in several clashes with the neighbouring Urbino.
Towards the end of the XII century, Montegridolfo was assaulted by troops from the municipalities of Mondaino and Saludecio and the records reported that books and sacred vestments were burned and that "houses, cellars and woodland were plundered and destroyed".
Located on a hot spot between two rival seigniories, the Malatesta from Rimini and the Montefeltro from Urbino,  the hamlet went through periods of strife. One amid the bitterest dates back to 1336, owed to an intestine clash between the Malatesta, conducted by Ferrantino Novello de' Malatesti, Galeotto Malatesta’s cousin, who had leagued with the Montefeltro and caused great damage to the castle. Two years later though, Galeotto Malatesta rebuilt it, and enclosed it with new fortification walls, strengthened with four powerful embattled towers, to the inhabitants’ great satisfaction.
The castle stayed in Malatestian hands until 1500, when it was handed over to the duke Valentino Borgia. The latter was defeated in 1503 by Pandolfo Malatesta, who sold the territory to the Repubblica Veneta, which after six years passed it on to the Papal State.
In 1769, monk Lorenzo da Montegridolfo became pope with the name of Clemente XIV. In 1849, with the proclamation of the Roman  Republic, Montegridolfo returned to its original bulwark function, until in 1860 a plebiscite united it to the Kingdom of Sardinia. 

Monuments