This dissertation addresses the critical need for youth inclusion in the evaluation of outdoor community spaces (OCS) through the development of pilot youth-engaged workshops. Grounded in strengths-based theoretical frameworks, the workshops emphasize identifying and leveraging individual and community assets to foster positive development. The workshops use participatory action research principles, positioning youth as active researchers and equipping them with the skills and knowledge to assess their local environments; encouraging youth to recognize and build upon existing resources and empower them to shape their OCS. The study is motivated by the understanding that adolescents' engagement with their surroundings significantly influences their well-being, sense of belonging, and overall development.The research employs a mixed-methods approach to comprehensively evaluate the pilot workshops. Quantitative data include pre- and post-workshop surveys measuring changes in developmental outcomes and youth participants' perceptions of their communities, as well as youth assessments of individual activities. Qualitative data was collected through arts-based activities and transcripts of activity discussions, and analyzed thematically to identify recurring patterns, themes, and narratives related to youth experiences. Quantitative and qualitative findings were integrated to gain in-depth insights into the experiences of youth participants, their perceptions of the workshop activities, and the perceived impact of the workshops on their personal and community development. The expected outcomes of this dissertation include developing a replicable and scalable model for youth-engaged workshops focused on evaluating OCS, as well as a youth-engaged audit tool reflecting their needs and preferences. The workshops and audit tool will be parts of a multifaceted toolkit, developed with youth input, for young people anywhere to use to evaluate their OCS. The research considers the need for a range of culturally responsive methodologies that allow youth to apply their contextual understanding when generating and analyzing data. The findings will offer valuable insights into the factors contributing to the success of such workshops in promoting positive developmental outcomes, such as increased competence, civic engagement, and a sense of belonging. This contributes to the fields of youth development and participatory action research by providing evidence for the effectiveness of strengths-based, youth-engaged approaches to evaluating and reimagining OCS.