Few Italian villages have their name explained in as many ways as this one, and every explanation has its author. For one scholar it comes from a feudal lord called Cacciaguerra, for another from the Vinciguerra family, for a third from a Latin contra, «opposite» a village called Guerra that nobody has ever found; others read in it the memory of an armed clash, placing it in the Gothic-Byzantine wars of the sixth century, and a modern reading takes contra as «in protection of» and guerra as nearness to a frontier line. The last hypothesis is the one that stands closest to the language: contra would be the medieval contrata, that is the district, and guerra the word the Lombards brought with them for their disorderly way of fighting, opposed to the ordered Roman bellum — so either the district of the war, or the district of a lord named Guerra, because that too was a Lombard name.
The village stands where the Tronto today divides Abruzzo from the Marche and once divided the Kingdom of Naples from the Papal State, and it spent centuries being taken and taken back. In the Catalogus Baronum, Contraguerra is a fief that must supply four soldiers to the imperial army. On the fourth of February 1297 it swore fealty to the city of Ascoli; and between the twenty-sixth and the twenty-seventh of December 1459 Giosia Acquaviva took it back by night, whereupon Ascoli hastily put together an expeditionary force and reconquered it on the thirtieth of the same month — three days. In 1460, by order of the viceroy, the village was fortified, and it then took the drop shape its historic centre still has: the plan of the town is a military decision. In 1497, held by men loyal to France, it was besieged by Ettore Fieramosca. Long before, during a clash between the troops of Totila and those of Belisarius, the village had been destroyed and only the walls of the mother church were left standing.