Community Days, an innovative initiative to foster community service and civic engagement at the City University of New York’s new Guttman Community College, encourages students to perform volunteer work around the city. What makes the program unique are opportunities for students to take self-directed excursions and enjoy free resources in the city—activities not usually associated with service-learning. Including a component that the students identify as “Fun Day” in a program dedicated to volunteer service strengthens the program and increases the enthusiasm of the participants. This essay examines reflections completed by the students after participating in Community Days, considering their initial expectations and apprehensions, their experiences in unfamiliar environments, and the connections they draw between community service and “fun.” These reflections suggest that the two program components reinforce one another in building social capital. Independently navigating unfamiliar areas of the city challenges them and builds their sense of autonomy and control. Successfully completing new challenges, however simple—whether serving meals in a soup kitchen or riding the Staten Island Ferry—gives them an experience of earned success. Because Guttman allows the students agency to decide how (and ultimately if) they will participate, they take full possession of their accomplishments.