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This case study explores how a principal-led effort to design an inclusive, community-wide field trip in a rural Northern California school district was obstructed by district-level politics, despite clear alignment with the goals of a state-funded Community Schools initiative. Drawing on community schools theory, implementation science, and educational leadership literature, the paper highlights how politicization of public education can undermine equity-driven innovation. Through qualitative evidence (e.g., interviews, observations, and photos) this paper illuminates the lived experience of families, the outcomes of relational trust, and the emotional toll on school leaders facing systemic resistance. Ultimately, it raises critical questions about who gets to decide what counts as learning and how courageous leadership can create space for joy, belonging, and engagement.