The Out of School Learning landscape continues to be an emerging ecosystem of learning, particularly for the adolescent population. While the focus for elementary school-aged youth has often been on after-school programming offering safety, supervision, and homework help, research has indicated that this approach is not equally successful for the middle- and high school populations (Mahoney, Parente, & Zigler, 2009). This dissertation builds on an examination of Peer-reviewed literature pertaining to advances in the understanding of adolescent development, and theories of self-determination and career discernment are discussed in relation to adolescent engagement in programming. Results of a landscape study on Out-of-School and After-School programs for adolescents (aged 13-19), conducted within the geographic boundaries of a capital city school district in South Carolina, is summarized. Together these data provide a snapshot of opportunities available to adolescent youth, as well as identify content and geographic gaps that make the Out-of-School Learning landscape less accessible to this demographic at a time when it could be most beneficial. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]