This dissertation takes up landscape theory, community-engaged art education, and research-creation methodologies to ask how the creation of artworks can reveal insights into the social, political, and economic foundations of place, and how community artmaking can be used as inductive research to document experienced changes in place over time. This thesis conducts two concurrent projects that focused on Montréal’s Sud Ouest borough, the site of substantial re-development over the past 50 years. The first is a personal research-creation project using plein air landscape painting to theorize painting as fieldwork and research creation. The second was an eight-week community art class called Landscaping the City, which used community-based research creation methodology to conjoin participant artmaking with longform interviews. 17 participant-students engaged in a curriculum focused on the neighborhood’s past, present, and future, balancing skill building with conceptual concerns. To carry out these projects, I embedded in a small community art school and a grassroots anarchist development project which gave insight to how community members have self-organized to meet citizen needs. By thinking these projects together, this thesis theorizes how multimodal engagement with the built environment can help to democratize forms of engagement, make visible contradictory demands and desires for space, and foster civic interest and participation in processes of placemaking.