This paper tells the story of the Kensington Food Forest, an urban ecological oasis where food production, forest growth, and grassroots activism intersect. Set within the Kensington Public Housing estates on Wurundjeri Country in Naarm/Melbourne, Victoria (Australia), it stands as a site of local regeneration against and beyond industrialised food and waste systems. Conducted with the Kensington Circular Economy Precinct Community Group, this research foregrounds the often-overlooked impact of grassroots initiatives within circular transitions by co-creating indicators that capture the ecological, social, and pedagogical values these spaces (re)generate. Together, the community and researchers position regenerative circularity not as a technological fix, but as an embodied, relational, and pedagogical praxis. By tracing the social-material flows and knowledge generation within this landscape, we show how communities learn with place, each other, and more-than-human worlds, revealing how Food Forest Pedagogies of Praxis can make circularity truly regenerative through practices of emancipation.