The first document to mention Massa Fermana dates back to 1050, when it was under the jurisdiction of the Bishop of Fermo. The remains of Roman funerary inscriptions bear witness to an ancient past. In the 13th century it belonged to the Brunfort family; members such as Guglielmo da Massa and his son Valerio who were Ghibellines are remembered for the atrocious episodes of war that plagued the town until it returned under the rule of Fermo. In1808 the town lost its independence when it was annexed to Montappone and then regained it once and for all in 1816. The main tourist sites of interest are: the church of the Saints Lorenzo Silvestro and Ruffino, which contains a highly esteemed work by Carlo Crivelli, the Massa Fermana Polyptych, signed and dated 1468, the first known work of the artist in the Marche, and the Madonna and Child with Angels, a tempera on wood by his brother Vittore; the Picture Gallery housed in the Town Hall, which contains paintings by Vincenzo Pagani, Durante Nobili, Giovanni Andrea De Magistris, two frescoes, a multicolour bass-relief in papier mâché and church furniture and furnishings that came from the convent of San Francesco; the Museum of ancient occupations, dedicated to the professions of bygone times and which documents in particular the professions of the cobbler and barber; the Straw Hat Museum, dedicated to a local specialist tradition, with tools for working straw and some examples of hats.