How can humans transcend their human perceptions and explore more-than-human experiences in arts education events? This question was explored in an iterative process of playful arts-based workshops rooted in posthumanism. Two workshops were organized as ‘walk-shops’ in the local environment and involved various approaches to engage with more-than-human experiences. Each walk-shop evolved from an affirmative response to a previous workshop experience. The paper discusses how these playful continuations can fuel radical imagination and transformation. We argue that workshops can develop iteratively when one actively pays attention to the situated possibilities within the context of the arts education event.