The Access to Care (A2C) is a multi-site initiative that seeks to increase the access to and retention in effective HIV healthcare and support services by people living with HIV across the United States. As the initiative implemented evidence-based programs in new settings with diverse populations, it was important to document these innovative efforts to contribute to the evidence base for best practices. In a partnership between Johns Hopkins University, AIDS United, and the A2C sites, a national evaluation strategy was developed and implemented to build knowledge about how linkage to care interventions could be most effectively implemented within the context of local, real-world settings. This article provides an overview of the efforts to develop and implement a national monitoring and evaluation strategy for a multi-site initiative. The findings may be of utility for other HIV interventions that are seeking to incorporate a monitoring and evaluation component into their efforts.