In the winter of 1933, eighteen-year-old Patrick Leigh Fermor set out on an adventurous walk across Europe, starting in Holland and ending in Constantinople. Decades later he would tell the story of that journey in his books A Time of Gifts and Between the Woods and the Water that would immediately grasp the public attention and ultimately make him the most acclaimed British travel writer of the twentieth century. The final volume of his conceived trilogy The Broken Road: From the Iron Gates to Mount Athos appeared posthumously in 2012, a year after his death. In the course of that journey, Leigh Fermor not only crossed the borders of several countries, but also the borders of two former empires – the Ottoman and the Austro-Hungarian one, the presence of which could still be felt decades after they had ceased their existence. An intelligent and curious observer, Fermor offers interesting examples of this ineffaceable presence. This is most evident in his description of Transylvania, which he considers a part of central Europe and something quite different from the rest of Romania, and also in his description of Bulgaria, where he finds clear traces of the Ottoman legacy, the crossing of the Danube seen as entering into the Orient. This paper presents and analyzes those examples of imperial legacies in the Balkans in the 1930s.