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Food system sustainability, and ways of measuring it, are widely explored and discussed in academic literature. Measurement efforts are challenging because food systems are inherently complex and multifaceted, spanning diverse components, indus­tries, sectors, and scales. Several systems of indica­tors and metrics have been proposed to measure sustainability; however, most existing research focuses either on narrow scales (e.g., farm level or within a single supply chain), expansive scales that can gloss over complexity (e.g., national or global assessments), or limited scopes (e.g., only consider­ing environmental factors). A gap in the literature is a holistic local or regional approach to food sys­tem sustainability that integrates components across the system at a regional scale. In this reflec­tive essay, we describe our development of a framework to measure and track sustainability in such systems. We use a tiered framework that includes five sustainability dimensions and a system of indices, indicators, and metrics that allows for the measurement of important food system charac­teristics in a feasible and reproducible way. We employ a collaborative, transdisciplinary, facilitated team science process to first propose, and then refine, a sustainability assessment framework, using the U.S. state of Vermont as a case study. This paper details our process and progress, as well as reflections on challenges and recommendations for other team scientists. We further propose a plan to implement the framework, collect data, and engage with community members. The experiences and findings described here serve as a foundation for our own team’s continued work, as well as a springboard for other similar research efforts.