In 2019, the New York Olympic Region received the first Leadership in Energy and Environmental Design (LEED) for Communities Certification (gold) for a rural multi-jurisdictional region comprised of Lake Placid Village, North Elba Town, the Olympic Regional Development Authority, and the Lake Placid School System. Much of the work involved in this initiative was executed by 14 undergraduate students and two faculty members from Clarkson University working in partnership with the U.S. Green Building Council, and four local jurisdictions. The endeavor was successful and unique in several facets. First, it provided an experiential project-based education in the application of a sustainable holistic planning system, LEED for Communities/Cities. Second, it demonstrates the value of a university collaboration with a rural region and its communities. Third, it developed the first rural regional model for smart community planning that integrated multiple jurisdictions and stakeholders. Finally, it provides a replicable template for implementation and operation by other communities with institutions of higher learning. A variety of challenges remain, however, for emerging sustainable holistic planning systems in metrics development, civic and stakeholder engagement, determination of efficacy, and implementation optimization. Readers will emerge with an improved understanding of sustainable holistic planning systems, knowledge of multi-jurisdictional planning concerns in sustainability metrics, and insight into implementation of these systems as a pedagogical tool and partnership mechanism.