Wilderness landscape, a setting common in Romantic literature and painting, is generally overlooked in the art of the Middle Ages. While the medieval garden and the city are well mapped, the medieval wilderness remains relatively trackless. Yet the use of setting to represent interior experience may be traced back to the Neo-Platonic use of space and movement to define spiritual development. Separating themselves as far as possible from the material world, such writers as Origen and Plotinus avoided use of representational detail in their spatial models; however, both the visual artists and the authors who adopted the Neo-Platonic paradigm, elaborated their emotional spaces with the details of the classical locus amoenus and of the exegetical desert, while retaining the philosophical concern with spiritual transition. Analysis of wilderness as an image for spiritual and emotional transition in medieval literature and art relates the texts to an iconographic tradition which, along with motifs of city and garden, provides a spatial representation of interior progress, as the medieval dialectic process provides a paradigm for intellectual resolution. Such an analysis relates the motif to the core of medieval intellectual experience, and further suggests significant connections between medieval and modern narratives in regard to the representation of interior experience. The Divine Comedy and related Continental texts employ both classical and exegetical sources in the representation of psychological transition and spiritual conversion. Similar techniques are also apparent in English texts such as Beowulf and the Anglo-Saxon elegies, in Geoffrey Chaucer's The Book of the Duchess, The House of Fame, and Troilus and Criseyde, and in the northern English The Pearl and Sir Gawain and the Green Knight. These literary texts, further, include both ideas and techniques which are analogous to those of visual arts, where frescos and altarpieces show the wilderness as metaphor for transition, and where manuscript illuminations relate this visual concept to texts. Thus, the wilderness as a landscape of personal crisis becomes in the Middle Ages a significant part of the representation of interior experience in painting and in literature.