He was dubbed a Knight of the Holy Sepulchre and was also inducted into the Order of the Jar and the Order of the Dragon. He lived for a time in Seis am Schlern.
Oswald's father was Friedrich von Wolkenstein and his mother was Katharina von Villanders. When he was ten years old, Oswald left his family and became a squire of a knight errant. Oswald described the journeys undertaken by him in the following 14 years in his autobiographical song "Es fügt sich...". He mentioned his travels to Crete, Prussia, Lithuania, Crimea, Turkey, the Holy Land, France, Lombardy (i.e. what is known today as Northern Italy) and Spain, as well as being shipwrecked in the Black Sea.
After the death of his father in 1399, Oswald returned to the County of Tyrol and began a quarrel with his older brother Michael about their inheritance. From 1401 to 1402, Oswald participated in the failed Italian expedition of King Rupert of Germany. In 1407 he and his brother agreed on how to split the inheritance: Oswald received a third of Castle Hauenstein and the accompanying estates in Seis am Schlern. The other two-thirds of the castle belonged to a knight named Martin Jäger, but Oswald did not respect the property situation, occupying the entire castle and appropriating Jäger's share of the tithe. In 1408, in preparation for a pilgrimage to the Holy Land, Oswald paid for a memorial stone to be installed on the wall of the cathedral in Brixen. The stone has survived and shows him in the garb of a Crusader, with the long beard associated with pilgrims. Before he left, he wrote several songs for his beloved, Anna Hausmann, the wife of the Brixner burgher Hans Hausmann. After his return in 1410, he acquired the right to take up residence in Neustift Monastery, an Augustiner-Chorherren cloister near Brixen.

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