Following previous studies about Writing and Seeing, this paper focuses on the aesthetic assumptions within the concept of Winter Journey (Voyage d’Hiver/Winterreise) both in Georges Perec’s Saga and the Oulipo Group vis-à-vis with the creations by William Kentridge and Michael Borremans. The aesthetic and artistic connections are widespread. Nevertheless, we can identify common poetical principles shared by these different authors, not only according to the notion of ekphrasis, but also following the procedures of contemporary creation in literature and visual arts. The analysis of the ongoing process of the French writers as individuals and as group and the visual artists’ acting might contribute for another crossed definition of contemporary conception. The same title/theme was a challenge and a goal for them. Let’s wonder how deep the concept encouraged them and which symbolic upbringings were directing their poetical achievements. The idea of an inner journey became the main point, and got “over” and “across” a shared path worth to be followed. The authors were chosen due to the resilient contents of their visual and written images, and looking for the reasons that might had driven their conceptual basis to be. In Pérec’s “Winter Journey” as for the following fictions by Jacques Roubaud, Hervé le Tellier, Jacques Jouet and Hugo Vernier (that emerges from Perec’s fiction and becomes a real author) powerful aesthetic and enigmatic reflections grow connected with a poetic (and aesthetic) understanding of Walkscapes. They might be assumed as ironic fictions and poetical drifts. Outstanding from different logics, the overwhelming impact of Winterreise Lied by Schubert after Wilhelm Müller’s poems is a major reference in present authorship creations. Both Perec and Oulipo’s author’s texts are powerfully ekphrastic, although we should not forget they follow goals, frameworks and identities. When acting as a reader, they induce powerful imageries - cinematic or cinematographic - that flow in our minds. It was well-matched with William Kentridge animated video Winter Journey (2014) and the creations (sharing the same title) of Michael Borremans (2014) for the KlaraFestival, Bozar, Cité de la musique, in Belgium. Both were taken by the foremost Schubert’s Winterreise. Several metaphors fulfil new Winter Journeys (or Travels) that were achieved in contemporary art and literature, as it once succeeded in the 19th century. Maybe the contemporary authors and artists were compelled by the consciousness of nothingness, although outstanding different aesthetics and ontological sources. The unbearable knowledge of the road’s end, and also the urge of fulfilling the void might be a common element to all of them. As Schopenhauer once wrote, after all, Art is the only human subjective power that we can call upon in life. These newer aesthetic meanings, released from these winter journeys are surely open to wider approaches that might happen in other poetic makings to be.