The history of Loro Ciuffenna has only maintained apparently tenuous traces of ancient times. It will be necessary, therefore, to refer back to a famous past that was cited many times by Livy [Titus Livius], who spoke explicitly about the Etruscans who settled in these zones:
"Regio erat in primis italiae fertilis, Etrusci campi, qui Faesulas inter Arretiumque iacent, frumenti ac pecoris et omnium copia rerum opulenti" (Ab Urbe condita Libri, Liber XXII, Cap. III).
But in addition to this testimony, there is by now much evidence of the presence of the Etruscans.

The same Ciuffenna torrent (whose name was added to that of Loro in 1862) is unquestionably of Etruscan origin: the name probably derived from cefa, deer; and also the locality of Gropina is supposedly a derivation from the Etruscan word Krupina.
The wealth of these lands and the trace that has remained in them of the Etruscan and Roman dominations is linked not so much by the albeit important exploitation of the local economic sources , but rather on the roads.

It is irrefutable that the fabric of roads that crossed this zone was such to create the conditions for it to come very soon in contact with Rome, which was then about to become the principal economic and political power in the peninsula.
After a first period of peaceful cohabitation between the Etruscan social élite and the Roman political class, starting from the 2nd century BC, the political climate began to change. Also in Etruria, an attitude of particular aversion to Rome and to its politics, which were openly favourable to the large landed estates, had emerged.

Here, as elsewhere, episodes of servile revolts due to widespread discontent were being registered.
After Silla's destruction of Arezzo, a real and proper political and social turning point occurred with Julius Caesar, who gave rise to a re-ordering by the region that had the foundation of the pilot colony of Florentia as its salient episode. Caesar's interventions represented a factor of further ostracism for this territory: from then on, the main axes of the imperial road network tended to avoid it, so as to travel long distances of a lesser length. Subsequently remaining excluded from the course of Hadrian's new Cassian Way, the zone was still served by the route of the pre-existing Cassia Vetus.

Along this route, studded with numerous human settlements, findings of manufactures and tombs were frequent. These were particularly interesting, because they supplied an indirect indication also of the less-important roads of which no trace exists in other types of sources.
In the entire zone of Loro, the Roman colonisation created "the conditions for a widespread presence of settlements" (Luglioli, 1989: 2) of which we can also hypothesise a certain territorial order: in fact, those on the right bank of the Arno "were arranged at least in triple file, according to the bend of the river, and are connected by a road system with networks that were rather impenetrable, to the point of constituting a reticular strip that has the Arno and the provincial Via dei Sette Ponti as parallel lines, and the other roads as transversal lines", which appear to follow eminently the course of the torrents which then flowed into the Arno as, for example, the Oreno and the Agna (Romby, 1977: 7).