Ledesma’s strategic location, by the side of the River Tormes, made it easy to defend. This, along with the menhir and the verraco (prehistoric sculpture vaguely resembling a boar), suggest the existence of a prehistoric castro as the first settlement in this place.

The Roman age remains that have been found, speak of a place of a certain importance. Some examples include the Puente Mocho bridge, that of Peñaserracín, or the bridge that, in its final stretch, crosses the Merdero stream. Another Roman trace is the Augustus boundary stone which nowadays is set on the north-east wall of the Santa María la Mayor church.

The  Muslim presence is remembered here by a popular legend that tells us about the martyrdom of Nicolasín,son of the Arabic lord of Ledesma, who had converted to Christianity, and of the priests who had baptised him.

With Fernando II of Leon, the definitive Christian re-population begins, as well as the city walls and, last but not least, the granting of the Charter in 1161. This was the beginning of a golden age for Ledesma, which became an important political centre as well as a key strategic point for the communication between the north and the east of Leon. In addition to this, Ledesma was at the centre of the relations between the surrounding villages, since at the River Tormes ford there was a crossroads of several livestock paths.

Later on, during medieval times, Ledesma earned and lost its feudal status, until 1462 when King Enrique IV ceded this domain to his favourite, Don Beltrán de la Cueva, Duke of Alburquerque, who then became the first Count of Ledesma and imposed his coat of arms on the town which, since then and until dissolution of the feudal regime in the 19th century, belonged to his legitimate descendants.

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