Amidst a climate crisis induced by settler colonialism and capitalism, education is key to developing new tools and envisioning solutions. Fostering skills for children to critically engage with systems of power is fundamental to how the next generation will address urgent global issues. Drawing on decolonial methodologies outlined by Linda Tuhiwai Smith (2012) and Zoe Todd (2016), I question whether play-based models are successful in teaching activist thinking in Canada. As an educational framework, play-based learning is gaining interest, particularly following the COVID-19 pandemic that required children to adapt to outdoor learning. Forest Schools Canada is one example that claims to revolutionize how children interact with the natural world to develop eco-stewardship skills in an age of ecological collapse. However, I find that mainstream play-based methods are not necessarily radical when examined alongside Indigenous land-based learning. Both frameworks prioritize intergenerational relationship-building, immersive storytelling, and hands-on learning outdoors, but the intention behind Indigenous land-based learning is inherently decolonial and anti-capitalist by necessity; conversely, play-based learning can inadvertently perpetuate these damaging systems. Using auto-ethnographic professional experience, governmental policies, and Sandra Harding’s (2016) work on standpoint theory, I critique current examples of Canadian play-based education concerning their effectiveness in teaching activist thinking. I rely on Indigenous scholars in New Zealand and Turtle Island to inform academic theories of land-based learning with examples, supported by interviews with former Indigenous colleagues in eastern Canada. My narrative-like writing and inclusion of practice-based methodology—two video conversations—deviates from traditional qualitative research to foreground relationships consistent with the frameworks I discuss. Though play-based learning shows limited promise in deconstructing harmful structures of power, especially within established western contexts like public schools, storytelling has potential to generate meaningful change if layered with intention, such as naming root causes, linking to current affairs, and inviting creative solutions through play.