It was Roman municipium, but still first it was very probably a place of the Etruria, as they make to think cippi, epigraphs, statues, bas-reliefs, architectural fragments and some objects found again on the spot (a bronze mirror is interesting a great deal with engraved figures). In Roman period it belonged to the sixth region augustea. His inhabitants, the Sestinateses, are remembered by Plinio in the natural History.

Its initial history was marked by various warlike stories for its position of border among the region etrusca and that umbra, to the limit of the zone occupied by the Roosters, when the people occupied the inclusive territory among the Rubicone, the Esino, the Alpe of the Moon and Mouth Trabaria up to Mouth Serriola and to the Footstep of the Splinter.

Beginning from 1520 it passed under Florence, that sent a commissioner to hold up the town. Around halves the Century XVI, in 1566, Cosimo I had a fortification to build on the near Stone of Simone as stings advanced of his power toward the Brands and Romagna.
Sestino was center of Vicariato and of Headed up to 1737.

The Stones of Simone and Simoncello, together with the statue of Voluseno, they are the symbols of the earth sestinate.
The Stone of Simone, the tallest of the two mountains, characteristic for their form to bread of sugar, beginning from 1566 and for wish of Cosimo I, it was center of a fortitude for the residence of a captain and a court that administered the justice in the earths of Abbey Tedalda and Pieve S. Stefano.

The garrison was strengthened in 1593, when they spread founded fears that the Montefeltro passed Center to the Saint. Following the following stories, that they saw to consolidate themselves in a situation of relative peace these earths, the Fortress of the Stone of lost Simone her importance and she was reduced to the function of simple garrison and then abandoned and dismantled.

Today The Stones of Simone belong to a beautiful Natural Reserve of 1500 hectares.