Founded by Afonso IX of León, who donated the town to count Rodrigo Gonzalez de Girón, Castelo Rodrigo retained the name of its settler. It passed to the Portuguese crown under the treaty of Alcanices, signed in 1297 by the poet-king D. Dinis of Portugal.

Castelo Rodrigo still bears the signs of former territorial dispute. The first of these took place during the dynastic crisis of 1383-1385. D. Beatriz, the only child of D. Fernando of Portugal, was married to the king of Castile. On her father’s death, Portugal lost its independence to Castile. Castelo Rodrigo swore allegiance to D. Beatriz, but D. João, the Master of Avis, defeated the Castilians at the Battle of Aljubarrota in 1385, and was crowned King of Portugal as D.

João I. As revenge for the lords of Castelo Rodrigo siding with Castile, the new monarch ordered that the town’s coat of arms should be turned upside down.

In the 16th century, when Philip II of Spain annexed the Portuguese crown, the Governor of Castelo Rodrigo, Cristóvão de Mora, took up the Castilian cause once more, only to suffer the anger of the locals who burnt down his enormous palace on the news of the Restoration (1st December 1640). The ruins on the hilltop bear witness to the Governor’s folly.

The town is also a resting place for pilgrims on the way to Santiago de Compostela, and St Francis of Assisi is said to have spent the night here on his pilgrimage to the saint’s tomb.