Trancoso's walled centre is a charming maze of picturesque squares, attractive churches and narrow cobbled lanes. Several medieval gates puncture the walls, including the Portas do Prado and, to the south, the Portas d’El Rei (King’s Gate), historically the main entrance into town – look for the coat of arms over the passageway. From either gate, it's a short walk to Largo Padre Francisco Ferreira, the handsome central square set around an octagonal 16th-century pelourinho (pillory). Nearby, the Igreja de São Pedro stands out, with its white baroque facade.

To the southeast is the judiaria, Trancoso's old Jewish quarter. Like many northern Portuguese towns, Trancoso acquired a sizeable Jewish community following the expulsion of the Jews from Spain in the late 15th century. As elsewhere along the border, you can generally spot Jewish houses by looking for a pair of doors: a smaller one for the private household and a larger one for a shop or warehouse. Among reminders of that time is a former rabbinical residence called the Casa do Gato Preto, marked with a Lion of Judah and other Jewish images.

Outside the northern walls, the 13th-century Capela de Santa Luzia is an attractive roadside feature, with its heavy Romanesque arches and unadorned dry-stone exterior.