This dissertation explores the local, material, and affective processes of Settler (non-Indigenous) attachment to land on southern Vancouver Island, British Columbia. I describe these feelings for land as Settler belonging and my research is guided by a reflexive and interdisciplinary approach that seeks to "explain Settlers to ourselves." Through original archival research and personal reflection, I argue that "(dis)possession," a term that encompasses Settler efforts to take the land and belong to the land, is a generational process, one that is worked at over time in an effort to link the past with the present and serve future Settler belonging. Through a study of plants, forest resource extraction, roads and railways, park creation, and real estate development in the Cowichan Valley and Sooke - Juan de Fuca regions, I argue that Settler feelings for land manifest in locally specific and contradictory ways. I contribute to the study of Settler colonialism and political economy in Canada by adapting the staples approach, as developed by Harold A. Innis, Mel Watkins, and others, to trace the intersection of belonging with the resource economy and the characteristics of Settler colonialism. This dissertation links historical and ongoing transformations in the relations of production, such as the conversion of private forestry lands into real estate, to reveal the ways in which belonging adjusts to political and economic changes that both assist and threaten its future. I argue that studying the locality of belonging contributes insight and nuance to our understanding of materiality and affect, class relations, the staple economy, and Settler colonialism's broader processes. In doing so, I demonstrate that Settler attachment to land is entrenched and expanded through a series of recurring events that are shared, personal, and conflictual.