The small municipality of Gagliole was once part of the Duchy of the Da Varano family and immediately after 1274 Gentile da Varano had the Fortress built to protect his territory. It is the only example of the Varano defence system. The imposing pentagonal keep, was built with vertical curtain walls made of locally sourced limestone and sandstone. Besides the fortified castle, other places of interest in the area are the churches of San Michele Arcangelo and S. Giuseppe and the Madonna delle Macchie Sanctuary. This latter complex is made up of a four-sided portico overlooked by monastic buildings and two churches. The oldest of these churches is a Gothic construction with pointed portals and cross vaulted ceilings, inside of which there are various frescoes attributed to the 14th century painter Diotallevi di Angeluccio and other paintings, now partially detached and conserved in the Diocesan Museum of Camerino, dating from the 15th century and created by an anonymous artist known as ‘Maestro delle Macchie’. In the other church, a particularly noteworthy work on the apsidal wall is the large Signorelli-inspired Assumption dating from the period between the 15th and 16th centuries. Gagliole lies within the Monte San Vicino and Monte Canfaito Regional Nature Reserve.  The Environmental Education Centre (CEA) of the Grilli and Elce valleys, with its headquarters in the municipality, promotes the awareness and use of natural resources present in the territory. An important venue regarding this area of interest is the Museum of Natural History, run by the Oppelide Foundation inside the 14th century Palace opposite the G. Varano Fortress. It contains numerous fossils and minerals that provide an account of how life evolved throughout all the geological areas. The exhibits on show are in an excellent state of conservation and come from the Elce valley as well as from other places, include outside of Europe. The finds include not only rare items but unique ones too.