Faint traces of what was probably a pre-Roman settlement at Sestino, dating to the fifth century BCE, were found in the district of Travicello, in the northeast of the current town, while an inscribed, bronze etruscan mirror from the sixth century BCE was found in the area of Lucemburgo, about four kilometres to the southwest of Sestino. These finds indicate that there has been a settlement here since ancient times, forming a control and rest point on the routes that go from the Tiber Valley, an area of contact between the Umbrians and the Etruscans, through the Marecchia Valley to Verrucchio and Rimini, and through the Foglia valley to  Carpegna and Pesaro. In the third century BCE Sestino was already a flourishing town in the Apennines, placed in a strategic position between the Tiber Valley and the Adriatic coast, under the control of the Clustumina tribe. An Aes Signatum, which is a lump of embossed copper used as money, dates back to this period and has an inscription in the Umbrian language “VUKES SESTINES” the meaning of which could be the village or sacred woods of Sestino. The inhabitants of this area, frequented by Umbrians, Piceni  and populations from the Po and Adriatic coast, in 90 BCE became cives romani, with the transformation of the Apennine village into a Roman Municipium or municipality. Even though it was not a very large town it was none the less an important centre for merchants and travellers along the axis between Rome and the Adriatic where ships berthed having come from the orient and from Greece laden with precious merchandise. It served as a residential centre for the ruling classes and offered all the necessary services for the surrounding agricultural and pastoral community.  The presence of a Roman settlement in the area of Sestino is, in fact, evidenced by the numerous place names that  derive from Roman origins (Presciano, Valenzano, Rotolano, Martigliano). The remains of the Roman town have been found mainly in the area above the medieval town, in an area of more recent expansion, around the parish church of  San Pancrazio, approximately corresponding to the ancient Forum. The centre of the Roman city developed along the hillside and was constructed with descending terracing that followed the shape of the land. It was placed in a strategic position near the confluence of the rivers Seminico and  Pisaurus, now the Foglia. The possibility that the town may have been walled comes from evidence found during work on the north west edge of the settlement, just south of viale dei Tigli, of a wall made of large blocks of stone. Evidence of the structure of the municipality municipium and the good standard of living enjoyed by the population is seen in the archeological digs  carried out within the modern town, some of which are on display in the Antiquarium and in the  Statuary collection in Sestino. Amongst other items there are the remains of the Roman baths, a domus  or large house, at the edge of viale dei Tigli, two buildings next to the Health Centre along the same road, a second  domus found under the rectory of the church of  San Pancrazio, some work spaces below viale dei Tigli behind the Nursery School, some statues and stones that decorated the Forum, a funeral mausoleum and numerous epigraphs that narrate the public and private history of the town. The archeological evidence coming from chance finds and more recent excavations tell the story of the Roman municipality until after the era of Late Antiquity when the flourishing town began to decline, no longer being on the main routes of communication.  The dedication to Genius Curiae inscribed in the epigraph that was reused as the base for the altar in the church of  San Pancrazio, is dated to 375 CE and is evidence of a still active municipium. However, the fact that the inscription was inscribed onto an already, previously used stone would indicate a scarcity of new stone and therefor a decline in production activities. For Sestino, as for many other Italian towns, the end of the Roman Empire meant the beginning of a new story, the most distant traces of which, for Sestino, could be the construction of a circular building  in the sixth century CE, identified from the architectural remains emerging near the apse of the church of  San Pancrazio and thought by some to be an  ecclesia baptimalis. History, from the fifth century onwards, tells of Sestino coming under the control of the new capital,  Ravenna and thus of the arrival of the Lombards. Their expansion as far as Pesaro in the eighth century CE meant the isolation of Sestino and thus its rapid decline. In the tenth century Sestino was assigned to the Counts of Carpegna by Otho 1 and two centuries later it passed into the control of the Dukes of Urbino,  and finally in 1441 it came under the dominium of Florence.