Context: Rural populations experience both a higher prevalence of and risk for premature death from chronic conditions than do their urban counterparts. Yet barriers to implement community-based chronic disease self-management programs persist. Program: The Living Well program, a multi-sector collaboration between a rural health care system and a network of community-based organizations, has offered the 6-week evidence-based Chronic Disease Self-Management and Diabetes Self-Management workshops since 2017. The program was a response to a quality improvement initiative to improve hypertension and diabetes outcomes throughout the health care system. Implementation: Using the rapid cycling quality improvement process, Living Well developed a self-management program recruitment, referral, and coordinating office for a six-county region. Through continuous capacity-building efforts with community partners, as well as leveraging key health care system assets such as the electronic health record and provider detailing, program reach and adoption was increased. Evaluation: The Reach, Effectiveness, Adoption, Implementation, and Maintenance framework was used for the process evaluation. During 3 years, more than 750 individuals engaged with the program, with nearly 600 completing a workshop. The region saw increased engagement by primary care clinicians to refer, and structural changes were embedded into the health care system to facilitate clinic-community partnerships. Discussion: A coordinated, multi-sector approach is necessary to develop solutions to complex, chronic health problems. A regional coordinating hub is an effective strategy for implementing community-based programs in rural areas. However, low health care system engagement and fragmented funding remain as barriers to optimal implementation.