Some of the author's most valuable experiences as a library media specialist (LMS) were not in a school library. Rather, they were on the streets of Chicago, in community gardens, and on the rooftops of buildings in Humboldt Park, where she was hired by the University of Illinois Community Informatics Initiative as a graduate assistant and LMS in training to work with Pedro Albizu Campos High School (PACHS), an alternative high school on Chicago's west side. In this article, the author shares her experience in working with PACHS as a library media specialist and in assisting students of the Urban Agriculture Initiative at PACHS. The author describes a community-based approach to teaching 21st century skills outside of the school library through the practice of urban agriculture. While working outside of a large school system lends itself to this type of grass-roots work, it is possible to perform in a similar capacity within the formal framework of a K-12 library media center program. Defining the role of an LMS in a similar community-based learning initiative within a school library might include: (1) Identifying Critical Resources; (2) Engaging Disconnected Youth through Community-Based Learning; (3) Designing Opportunities for Inquiry-Based Learning; (4) Teaching 21st Century Skills; and (5) Developing Opportunities for Authentic Assessment.