This study consists of the practice and research of theatrical clowning and nature as a world view towards a scholarship of feeling. The assumption of this study is that clowning and land relationship connect through their potential to catalyze and support personal inquiry and growth. The goal of this doctoral research is to articulate a theory and practice of Natural Clowning as inquiry. This study uses arts-based research and more particularly, clowning and nature as a world view as techniques to connect to feelings through play, humour, story, sensory connection, dramatic reality, physicality, and authentic impulse, to thus access parts of the unconscious, and to integrate these parts of self into awareness. I believe these parts, when allowed to express or communicate in their own right, may offer not “right” answers per se but honest answers with the potential for great wisdom. Although this doctoral study began as a question as to how clowning could inform ecological activism, it became a healing journey for me towards wholeness and what it means to be in relation with self and others, both human and other-than-human, as a settler of British ancestry living in Mi’kma’ki. I documented and artistically expressed experiences in clown trainings, performances, and experimental workshops, as well as mentorship and practice in land communication for three years (2014-2017) through reflective analytic memos, field notes, song, and storybook writing. I reference literature in diverse fields such as theatrical clowning, drama therapy, nature as a world view, child development, humour, and play. These references share space with stories that I hope will bring the literature to life. They are my own stories, and while they are personal to me, I believe they will have applicability to other Euro-settlers who are on a similar journey towards growth and wholeness.