The medieval town of Urbisaglia is enclosed by walls and dominated by a fortress built in the 16th century, whose keep dates back to the 12th century.
From the top it is possible to enjoy a wonderful view of the medieval town and of the territory between Monti Sibillini and Fiastra valley, from the mountains of the Fabrianese to the Adriatic Sea.
S. Maria del Massaccio Church (known also with the name della Maestà) is worth a visit, since it preserves a number of frescoes and ex voto, representing scenes of the popular and religious life of the 15th century.