The number of older adults residing in assisted living facilities (ALF) and utilizing adult day care services is expanding with the increasing population of older adults. Currently, there are no standardized requirements for continuing education for assisted living and adult day care service staff at a national level. Given that 62% of states within the United States require continuing education for ALF staff and/or administrators, a more formalized system is needed that provides evidence-based gerontological training to enhance the quality of care and services provided to older adults. This article describes the challenges and lessons learned from conducting a program evaluation of a Statewide Training and Continuing Education Program for Assisted Living Facility and Adult Day Care Service staff in Virginia. Survey evaluation data from a 6-year period was examined and a formative program evaluation was conducted. The findings from the survey evaluation and formative evaluation are discussed as are the lessons learned.