Hospitals and health systems, including those serving rural communities, are increasingly embracing population health strategies as they move toward accountable care models of health care delivery and financing and seek to re-focus their community benefit activities to improve the overall health of their communities, demonstrating their accountability to local stakeholders. This paper looks at the population health strategies of a geographically diverse set of Critical Access Hospitals (CAHs) to identify key challenges, opportunities, and lessons that could inform the efforts of other CAHs and state Flex Programs. This paper provides examples of eight CAHs and communities that have made substantial commitments to population health and community health improvement. Key themes that emerged from the qualitative interviews of the selected CAHs highlight the collaborative nature and the high level of community involvement of the various initiatives.