Following the road under the walls, you enter the famous straight road that, built at the end of the fourteenth century, still connects Anghiari with Sansepolcro. Arrived in the flat land you can see the historical cultivations of tobacco (where the raw material for the famous Tuscan cigars is produced), traces of the Roman centuriatio (the way the land was divided into smaller pieces) and the ancient Byzantine church of Santo Stefano.
A little further you’ll see one of the ancient mills (no longer working today) built on the so called Reglia, a ditch that was fundamental for the battle outcome. Walking along its border, surrounded by cultivated fields, with rows of grapevines here and there, you’ll Maestà di Santa Maria. It is a small chapel, built in 1441 to commemorate the victory: today it is the starting point of a race called the Palio della Vittoria, which is held on June 29th each year.