Trujillo was settled on a granite batholith during Prehistoric times. In Roman times the town was known as Turgalium and became a prefecture stipendiary of the Lusitaniancapital, Emerita Augusta. Later it was colonised by barbarian tribes (mainly Visigoths) although the prevalence of the population would still have been Hispano-Roman.
With the Muslim invasion and conquest in 711, it became one of the main towns in the region, governed by the Taifa based in Madrid. This taifa was subject to the Umayyad Emirate and subsequent Caliphate ruled through the middle of the 11th Century. During this time the ethnic tensions between the Berbers and Arabs weakened the Caliphate militarily while the Reconquista gained success to the north of Extremedura in Castile. During this time the Berber Almohads took control of Trujillo and it environs.
During the time of Almohad rule, civil wars between Portugal, Castile, and Leónguaranteed that Christian repossession of Trujillo was tenuous. Rulers alternated between these kingdoms and the Almohads returning for the last time to the Muslims in 1187.
Five centuries of Muslim occupation and control finally ended when an army formed by forces of the Military orders and the Bishop of Plasencia laid siege to the city of Trujillo with the support and blessing of Saint Ferdinand III. Muhammad ibn Hüd tried to relieve the town but was driven off by the besieging army.
The town was finally captured on 25 January 1232. During the final assault, according to the local legend, the Christian forces were faltering just short of victory when many reported seeing the Virgin Mary (known as Virgen de la Victoria in Spanish, or the Virgin Mary of Victory) between the two towers, or Arco del Triunfo, in the castle. Sufficiently inspired, Christian troops pressed on and achieved victory defeating the Muslims who were inside.
King Juan II of Castilla gave the town the title of city in 1430. Later it had a Jewish quarter