Oswald von Wolkenstein - a well-known minstrel, poet, composer and diplomat - was born around 1376 or 1377 at Scaunia Castle, or Schöneck Castle, in the Val Pusteria valley. He was one out of the seven children of Katharina von Villanders, from the important noble family of the Lords of Villandro, and of Friedrich von Wolkenstein, from the Lords of Wolkenstein. The home castle of this dynasty was Trostburg Castle, which nowadays houses the South Tyrolean Castles Museum.

Oswald von Wolkenstein spent most of his childhood years at Trostburg Castle. Around 1387, at the age of only 10, he left his home and started an adventurous vagrant life through large parts of Europe, probably as far as the Near East. At that time he already wrote ballads about Prussia, Hungary, the present-day Spain, Persia and other countries. When his father died in 1399, he returned to South Tyrol, where a long inheritance dispute with his brothers followed. Only in 1407, the inheritance was divided: Oswald von Wolkenstein received a third of Castelvecchio Castle (Burg Hauenstein) in Siusi allo Sciliar, the other two thirds were awarded to the knight Martin Jäger.

In 1415, Oswald von Wolkenstein took part in the Council of Constance following Frederick IV, Duke of Austria, and was subsequently taken up in the service of Sigismund of Luxembourg, Holy Roman Emperor from 1433. His task was to act as an intermediary between the king and the Tyrolean aristocrats who opposed the expansion of the sovereign power by Duke Frederick IV. In 1421, Oswald von Wolkenstein captured the entire income of Castelvecchio Castle, but only one-third of it belonged to him. Subsequently he was imprisoned at Forst Castle near Merano, and tortured. After years of escape and imprisonment, Castelvecchio Castle remained in his hands, but he had to pay the knight Martin Jäger a compensation and to swear an oath of truce.

Between 1423 and 1425, Oswald von Wolkenstein had a first manuscript made on parchment with more than 100 of his ballads, today known as "Manuscript A". In 1431, he became a member of the Order of the Dragon, a monarchical chivalric order for selected nobility, and prepared his second manuscript on parchment, the "Manuscript B". This allowed him to lead a noble country life. Together with his wife, he raised 7 children. In 1445, Oswald von Wolkenstein died in Merano as a highly respected knight and one of the most important aristocrats of South Tyrol. All portraits show him with his right eye closed. An examination of his skull revealed a congenital deformity of his eye level. A curiosity: Since 1998, also the asteroid (8316) Wolkenstein bears his name.