We have some documents about Citta Della Pieve from the twelfth century when, in a papal Bull of 1181, Pope Lucius III (1100 ca.-1185) granted to Guglielmo, Bishop of Lucca, some privileges. Lucius III, therefore, appointed: "[...] Castrum et curtem Sancti Gervasii cum omnibus quae eam pertinent [...]" ["the fortress and the Court of ‘San Gervasio’, with all its appurtenances"] (See “Memorie e Documenti per Servire all'Istoria di Lucca” [" The Memories and Documents to Serve to the History of Lucca"], Vol. IV, Part II, Lucca, 1836, p. 195).
The etymology is typically medieval, and it refers to the concept of a "castrum" ("Fortress"), around which there was a village with his "parish" (Latin "Plebs"), a name under which, in the Middle Ages, precisely the country churches were indicated. The old medieval name of "Città della Pieve" was then "Castrum Plebis" ("Fortress of the Parish Church"); then, when the surrounding village was enlarged to become a "city" (Urbs), there was a change of name, and it, from "Castrum plebis", changed into "Urbs Plebis", translated as “Città della Pieve” [“City of the Parish Church”]. It should be noted that the ancient name of “Castrum Plebis” remained a long time, and that the modern name was assigned to city at the behest of Pope Clement VIII (1535-1605) in the seventeenth century.
We know that the ancient "castrum" was a fortified outpost controlled until the seventh century by the Lombards. The "castrum" was then strengthened in 1326, with the building of "Fortress" by the Perusians, who after the death of Emperor Frederick II (1194-1250), forced it their rule until 1529, when Pope Clement VII (1478-1534) de Medici incorporating the town under the power of the Church State. The main buildings of Old Town were built between the thirteenth and sixteenth century, using the brick as a building material, of which “Città della Pieve” was, since the Middle Ages, a major production center. The trades of the city were helped by several routes that connected the important "Via Francigena" (so called because it connected Italy with France), located to the west; so the merchants of the city had access to that roads of international trade that crossed the whole of Tuscany to reach the Po River Valley.
“Città della Pieve” was located on another important route, the "Way of ‘Alpe di Serra’". The road, recently discovered, was built by the Lombards as a link between the "Via Emilia" and "Via Francigena. The "Via Emilia" reached “Alpe di Serra” in Tuscan-Apennine, to the height of “ ‘Mandrioli’ Pass”; then it went down to Arezzo in the Arno Valley. From here, along the eastern part of the "Val di Chiana," headed for “Castiglion Fiorentino”, Cortona, Castiglione del Lago, Castel della Pieve, Orvieto and Montefiascone, where it joins the “Via Francigena”. These major road junctions thus promote trade in handicrafts of “Città della Pieve”, the economy of which still is hinged about working with clay, using the ancient craft techniques, and offering terracotta artefacts of considerable value. The city's economy also is boosted by tourism, thanks to the important artistic heritage, which is expressed mainly in the figure of Pietro di Cristoforo Vannucci, called the “Perugino” (1450-1523), who was born here.