With a past that parallels the history of Portugal, Trancoso is a town whose narrow streets and stone houses preserve the medieval atmosphere. The plateau on which it is situated, at an altitude of 870 metres, gave it a strategic position in the defence of the frontier with Spain and made it an important fortress during the Middle Ages.
The Porta d'El Rei is the main entrance in the walls and a homage to D. Dinis, who celebrated his marriage to Isabel of Aragon here in the Chapel of São Bartolomeu in 1282. D. Dinis presented the town to the Holy Queen as a dowry, and established the tax-free market, the origin of the great Trancoso fair that still takes place every 15th August, the day of Nossa Senhora da Fresta, the patron saint.
The labyrinth of stone streets leads to the town centre and the Pillory, where the Old Town and New Town meet. In the oldest part stands the Castle, much contested by Moors and Christians and finally captured by D. Afonso Henriques in 1160, and the Church of São Pedro, the eternal resting-place of the mysterious Bandarra (1500-45), a cobbler-poet who prophesied Portugal's loss of independence in 1580 and its restoration in 1640.
The population settled in the New Town. In the fifteenth century there was a large Jewish community that contributed much to the development of commerce. This period has left its mark in the architecture of the houses with two doors (a wide one for the shop entrance and a narrow one leading to the living quarters) and in the Casa do Gato Negro, or House of the Black Cat, (in the Largo Luís de Albuquerque), one of the town's most emblematic buildings identified as being the former synagogue and home of the rabbi.
Magriço ("the Lean One"), one of the "Twelve of England" and the protagonist of a historical episode between Portugal and England, lived here in the fourteenth century. It was also in this town that General Beresford set up his general headquarters in 1809 when he was in Portugal as an ally against the Napoleonic invasions. Five years later, Beresford was given the title of first Conde de Trancoso.
On 29th May the town celebrates the anniversary of the Battle of São Marcos (1385), precursor of the great victory of the Battle of Aljubarrota against Castile, in which D. João I defended and consolidated Portuguese independence. On this day bread and oranges are distributed to the children of the São Marcos plateau, where the battle was fought, because according to tradition the Portuguese left the Castilians to "bread and oranges"