This article focuses on the implementation and evaluation of "Art in the Moment," a collaborative program between the Art Institute of Chicago and CJE SeniorLife, a non-profit eldercare organization and service provider for the Chicago area. We joined together to develop and offer "Art in the Moment" as an arts-based therapeutic and wellness program for older adults living with Alzheimer's disease and related dementias. Anecdotal evidence led us to believe that the program was effectively serving participants, including caregivers, in ways that were positive and self-affirming. However, we also realized that more formal evaluation could help us better assess the efficacy and impact of our efforts. We discovered that the evaluation process presented various opportunities as well as challenges, which we will explore in this article.