Rua de Santa Maria is the oldest and most picturesque street in Guimarães’ old town, it meanders down the slope from north to south. Rua de Santa Maria boasts many sophisticated examples of 15th and 16th century architecture that were popular among Guimarães’ nobility and affluent families. The street was initially designed to connect the 10th-century monastery on the current Largo da Oliveira in the lower part of the city to the castle in the upper part.

The path is adorned with historic edifices such as the Casa do Arco, Casa dos Peixotos, the Gothic Casa dos Valadares, and the Convent of Santa Clara, one of the richest convents in Guimarães.