The nurturance of creative capacity and cultural awareness have been identified as important 21st century concerns, given the ways that globalisation has challenged cultural diversity. This thesis explores the share that the art classroom, as a formative place, has in supporting such concerns. It specifically examines artmaking strategies that visual arts teachers may use to help adolescent students to develop and negotiate their senses of self, place and community. Held within this goal is the assumption that both student and teacher perspectives are important to this endeavor. This thesis, accordingly, draws upon empirical work undertaken with lower secondary school level visual art students in Christchurch, New Zealand and teacher-trainees in Kingston, Jamaica to explore this potential in multi-dimensional ways. The research employs a qualitative, arts-based methodology, centred on the transformative capacity of ‘visual knowing’ to render this potential visible. A/r/tography as a particular strand of arts-based methodology, served to also implicate my artist-researcher-teacher roles in the study to facilitate both reflection and reflexivity and to capture the complexity and dynamics of the study. Multiple case studies provided the contexts to furnish these possibilities, and to theorize the intrinsic qualities of each case, as well as the complementary aspects of the inquiry in depth. The conceptual framework that underpins this study draws widely on scholarship relating to contemporary artmaking practices, visual culture, culturally responsive and place-conscious pedagogical practices. The research findings reveal that when the artmaking experience is framed around the personal and cultural experiences of the participants, both students and teachers participate in the enterprise meaningfully as co-constructors of knowledge. In this process, students develop the confidence to bring their unique feelings, experiences and understandings to the artmaking process, and develop a sense of ‘insideness’ that leads to strong senses of self, place and community. This also creates a space where the authentic interpretation of artmaking activities goes beyond the creation of borders around cultural differences, and instead generates multiple entry points for students to engage with information. The findings also indicate that while the nature of artmaking is improvisatory and emergent, structure is an integral element in the facilitation of habits toward perception and meaning making. Accordingly, emphases on structured, open-ended artmaking experiences, framed aesthetically, as well as exposure to both the products and processes of contemporary art serve this endeavor. Artmaking boundaries and enabling structures also help to supplement this process. Though this research is limited in scope (in terms of the community engagement), there exists evidence that collaboration with community resource persons enlarges students’ conceptions of artmaking. It presents the potential to address broad issues of local and global import, which also have relevance for the ways students understand their relationships with the world. For researchers outside of the school and community culture however, this process requires close working relations with school personnel to ensure its effectiveness and to facilitate those school-community bridges. The undertaking is also best realized when participants have their own senses of its value, and, as such, are more inclined to participate. A/r/tography, as an arts-based methodology presents much potential for examining the complexities of the artmaking experience. As a form of active inquiry it helps those who employ its features to be more attuned toward enquiry, their ways of being in the world, the ways the personal may be negotiated in a community of belonging, and the development of practices that address difference. This contributes to evolving and alternative research possibilities that value visual forms of ‘knowing’. Finally, this thesis addresses the paucity of research on visual arts education at the secondary level, especially in the Jamaican context. A significant feature of this research is the evidence of its effectiveness with both lower secondary school students and teachers across geographical contexts. It therefore presents the potential for similar studies to be undertaken internationally. Given that the results are site specific however, it is recommended that the adaptation of the framework of this study for future purposes also respond to the specific realities of those contexts.