The Middle Ages
After the fall of the Western Roman Empire, which took place in 476 and up to the end of the 6th century, there is no relevant information regarding Pitigliano which, like all of Italy, suffered violent barbarian invasions.
At the end of the 6th century, southern Tuscany was conquered by the Longobards, who managed to subdue first the city of Roselle, in 592 and then the city of Sovana, in 603.
In 774, Charlemagne conquered the Lombard territories and in 787 donated the cities of Populonia, Roselle, Sovana and other small villages to Pope Adriano I, not without the hostility of the noble families of Tuscia – today’s Tuscany. It was one of these families, that of the Aldobrandeschi, that gained control over Pitigliano in 862, in the Carolingian age.
It was in the time of Aldobrandesca rule that we first gain written proof of Pitigliano’s existence, in a papal bull by Niccolò II of 27 April 1061.
In the 12th century, Pitigliano, together with the nearby cities, was part of a fiefdom between Sovana and Castro, controlled by a vassal of the Aldobrandeschi, Ranieri di Bartolomeo. Ranieri di Bartolomeo, given his relationship with the city of Orvieto, put Pitigliano under the town of Orvieto in 1168. When the feudal reign of the Terra Guineccesca by Ranieri di Bartolomeo ended, Pitigliano was taken over by the Aldobrandeschi. This caused deep discontent in the Orvietani, and in the 13th century, Orvieto and Siena fought constantly against the Aldobrandeschi. The clash ended with a union between Orvieto and Siena. The new power forced the Aldobrandeschi to accept a pact that expected them to continue to govern Pitigliano in exchange for the payment of a substantial tribute to Orvieto. The Aldobrandeschi accepted this despite the agreement but never renounced their rebellion and the Ghibellines soon obtained the support of the Emperors. In 1210 the emperor Otto IV recognized the Aldobrandeschi as the feudal lords of Guideccesca and in 1221 Federico II granted them one of the highest honours placing them above all the other lords of southern Tuscany. These honours led to the natural decay of the tributes imposed by the city of Orvieto. Despite this, the Orvietans did not surrender and in 1215 occupied the castles of the Aldobrandeschi and in 1216 divided county with the aim of conquering the Guideccesca. In 1223 the Orvietano captured Ildebrandino, Guglielmo and Bonifacio, imposed the payment of taxes on the Aldobrandeschi and took possession of the fortresses of Pitigliano and of the city of Vitozza as guarantee of payment. In the following decades, power passed to Count Guglielmo Aldobrandeschi who, by supporting the Guelph faction, also obtained the support of Orvieto, which has always sided with the Church.
In 1240 the troops of Emperor Federico II and those of Siena occupied the Aldobrandesca county and it was only thanks to the intervention of their new ally Orvieto, that the Aldobrandeschi managed to regain the territories, in 1250. The city of Orvieto still imposed taxes on the Aldobrandeschi as per the agreements of 1203.
In the second half of the 1200s a new enemy took on the Aldobrandeschi, the Republic of Siena, which, following the fall of its empire in Tuscia, aimed to destroy the Aldobrandesque county. Count Ildebrandino Aldobrandeschi, nicknamed Red, allied himself with the Florentines, mortal enemies of the Sienese, and took part in the Battle of Montaperti in 1260. Siena emerged victorious and captured Count Ildebrandino and over 400 soldiers from Pitigliano. Peace was stipulated with Siena only following the sale of the city of Grosseto.
Ildebrandino Aldobrandeschi then took part in the crusade led by the King of France’s brother, Charles of Anjou, against Manfred, son of Emperor Frederick II, who came out victorious. The count’s support was rewarded with the marriage between his, Margherita Aldobrandeschi , and Guido di Montfort, the Guelph vicar of King Charles of Anjou in Tuscany. The peace was however only momentary for the Aldobrandeschi, in 1272 Guido di Montfort killed Henry of Cornwall in the Church of San Silvestro in Viterbo, taking revenge for the murder of his father, who died during the war for the English crown. As a consequence of this act, Guido di Montofrt was immediately dismissed as vicar of Tuscany and Ildebrandino himself was suspected of having organized the tremendous murder and of helping his son-in-law escape
In 1274 the Aldobrandeschi County was divided between the branches of Santa Fiora and Sovana weakening considerably the power of the Aldobrandeschi, the county of Sovana was placed under the control of Margherita Aldobrandeschi but thanks to her private life “the fate of the county were never rosy.” Margherita in fact married five times, was excommunicated for having married a cousin in Santa Fiora, and in the chaos of her private life, the county that was submerged by popular revolts. In this atmosphere the Republic of Siena took over, succeeding in conquering Saturnia and Scansano. In 1293 the marriage between Anastasia Montfort and Romano Gentile Orsini was celebrated and at the death of Margherita Aldobrandeschi, in 1313, the county passed definitively to the Orsini.