Oswald von Wolkenstein was born around the year 1377, most probably in the Val Pusteria valley, and grew up at the Trostburg in Ponte Gardena, at the entrance to the Val Gardena. Oswald was a singer, composer and poet, who lived in the late Medieval era and was known far beyond the regional borders. He descended from the noble family of Villanders, who later on named themselves after Castel Wolkenstein in the Val Gardena valley. At the age of 10, he started an adventuresome vagrant life and travelled to the Near East, but returned to Tyrol in 1400.

As highly educated and widely travelled person, he was assumed at the Council of Constance in the retainers of Siegmund von Luxemburg and was henceforth mediator between the kind and the aristocrats of Tyrol. Oswald inherited one third of the Castel Vecchio in Siusi, but he snagged all the incomes and was therefore involved in serious struggles. When these problems finally were resolved, he married a woman, who gave birth to his seven children. His life became a little more calm, but from time to time he was still involved in different quarrels.

In the years 1423/25, Oswald worked out his first booklet with more than 100 songs, today known as the "Handschrift A". In the years to follow, there were the "Handschrift B“ as well as the "Innsbrucker Liederhandschrift", all written on parchment. In 1445 Oswald von Wolkenstein died in Merano as highly estimated knight and one of the most significant aristocrats of Tyrol. In Selva Gardena, Wolkenstein in German, today there is a library named after Oswald von Wolkenstein. In Siusi, Fiè allo Sciliar and Castelrotto, every year there is the famous Oswald von Wolkenstein horse parade.