Dickfeld was born on 20 February 1910 in Jüterbog in the Province of Brandenburg, the son of an artillery officer. In his youth he learned to fly glider aircraft. He made his first flights at the glider school in Grunau in Silesia, present-day Jeżów Sudecki, Poland. Here, among others, he was taught to fly by Hanna Reitsch. He was also trained by Wolf Hirth on the Hornberg in the Black Forest, and by Heini Dittmar and Oskar Ursinus at the Wasserkuppe in the Rhön Mountains.
