Stories about monstrous encounters during travel are ubiquitous in every culture. Scholars see them as figurative representations of the cultural anxiety related to traversing the unknown and the encounter with the “Other”. For instance, the early Greek 'monster-on-the-road' tales are often read in the context of the expansion of trade among Greek city-states and the Greek colonization of far flung territories which necessitated going beyond the safety of familiar town boundaries. The Indian epics and folktales also abound with encounters of travellers with supernatural/monstrous beings. Whether it is episodes such as the “YakshaPrasna” in the Mahabharata, or the Bodhisatta's encounter with the Naga and the Yaksha in Buddhist legends, or his encounter with Yakkhinis in the Jataka tales, travel often involved encountering the Dangerous “Other” who had to be defeated/satiated/converted. These early traveller's tales can be read as records of the anxieties regarding expansion/establishment of the Kshatriya hero's kingdom where the wild/primitive outside the bounds of civilization had to be conquered/appropriated. In the case of the religious hero, the monster represented a crisis of faith - either he/she was an embodiment of the allures of material pleasure the ascetic had to guard against or a staunch believer of another faith who had to be converted/conquered. All these “forgotten” traditions of travel come together in the Yakshi tales of medieval Kerala where a shape-shifting tree spirit haunting lonely pathways evokes memories of the ancient traveller's encounter with the wilderness and its corresponding deities. This paper attempts to read these tales from medieval Kerala against earlier Indian traditions of travel as well as the literal and metaphorical crossings of caste and gender borders that travel entailed during the medieval period. © AesthetixMS 2020. This Open Access article is published under a Creative Commons Attribution Non-Commercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/), which permits non-commercial re-use, distribution, and reproduction in any medium, provided the original work is properly cited. For citation use the DOI. For commercial re-use, please contact editor@rupkatha.com.