The road of Pietramala linked Arezzo to Anghiari and Sansepolcro, passing over the ridges that separate the basin of the River Arno from the Tiber Valley. 

This was one of the routes which, since ancient times, facilitated the trading to and from the ports of the Adriatic Sea (the second route was the so-called Via Ariminensis, built by the Romans, going from Arezzo to Rimini). In Medieval times, and especially in the 14th century, the Via di Pietramala (perhaps from the Latin petra mala, thus called because of the bad condition of the paving) was used so much that it took the additional title of Via dei Tarlati, named after the powerful family that linked its destiny to the short-lived fortunes of Arezzo. Bishop Guido, a professor at the University of Arezzo at the beginning of the 14th century, recognised the route and its resulting trade as a way to expand the city towards the Adriatic. This resulted from a desire of independence and also an attempt to escape the ever-increasing hegemony of Florence.
Flocks bound towards the Maremma for the winter passed along this rocky route, as well as great loads of woad, (the only vegetable extract to give fast blue dye). The importance of this road is noted by the presence of ‘ospitali’ built as shelters for travellers bound for S. Polo, Vezzano and Montecasale. Movement on the route was controlled from Tarlati Castle, on the site of Pietramala. Only some shapeless ruins of this castle are left, because in 1385 the Florentines completely destroyed it because of its strategic potential. From then on, the road became a decadent footpath and trade was moved to the adjacent road called ‘della Libbia’ where the Florentines built their garrisons. It is still used today to link Arezzo and Anghiari. The road of Pieteramala remained in the people’s memory, even though many man-made structures have disappeared; today it is completely accessible on foot and almost all accessible to mountain-bikes. On foot it is a very long excursion – 25.7 km – which can be done in two days, staying overnight in the cosy farm of La Scheggia, which can be reached by a detour from the main path. However, it is impossible to ride a bicycle after crossing Chiassa Creek- bicycles must be walked on the path.