Opportunity and learning gaps between upper-middle-class students and lower SES students that impact academic performance and social development are widening. The purpose of this Action Research study was to understand the interests of students, as well as the academic support most needed, to cultivate the development of 21st century skills and civic understandings. Participants in Cycle 1 included students, teachers, and the principal of Blue Valley School. Primary Cycle 1 themes from students centered on them sharing an openness toward pursuing wide ranging interests, including becoming more involved in the community, as well as an understanding of the benefits of hands-on learning and needs for more support in learning during the school day. These themes were echoed in teacher interviews where students' needs for supportive learning relationships were highlighted, as well needs for enrichment and clubs that reflected student interests. The Cycle 2 action step initiated interdisciplinary, curricular programming in ELA and religion classes through a PBL design aimed at cultivating 21st century skills and civic understandings. Students were engaged in reading novels about adversity and leadership and learning about UN sustainable development goals and Catholic social teachings, as well as understanding local needs from a wide variety of community speakers. Students applied new understandings in designing community-based projects that were meaningful to them. This study found that: (1) creating authentic opportunities to investigate and potentially impact civic issues greatly increases students' engagement and can be a vehicle for supporting the development of their 21st century skills, and (2) the design of activities and teacher scaffolding greatly contributed to students' exploration and understanding of civil issues and facilitated the development of their 21st century skills. It is hoped that interdisciplinary learning opportunities that promote student engagement in the community and the development of 21st century skills will be expanded through programming and relationship building that seek to bring Blue Valley School into the community and the community into Blue Valley School. [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/en-US/products/dissertations/individuals.shtml.]