What are the boundaries of art education? And what can we stand to subtract from it, while still allowing it to remain recognizable? These questions guided the authors', who are an assistant professor and a doctoral candidate in the field of art education-- developed a community art program in Tallahassee, Florida. The program, Artcation, took place during June and July 2016, offering three-hour sessions twice a week to a total of 15 youth, ranging in age from 6 to 13 years old. The program was free of charge to the public. Both expansive and limiting, they had find a way through with this term while building the program. This article explores, therefore, the word free as a paradox at the heart of this art education program. They review this paradox by moving through three theories that help them organize and orient their thoughts as they ponder the implementation and impact of this program: (1) a curriculum in abundance (Jardine, Friesen, & Clifford, 2006); (2) Kalin's (2014) critical examination of pedagogical paradoxes; (3) and Manning and Massumi's (2014) notion of enabling constraints. The authors' aim with this reflection is to develop a more nuanced awareness of the possibilities and challenges of free art education, which will inform future practices.