This thesis explores the intersection of community planning and historic preservation in Baltimore City’s Oldtown historic district. While the historic district has preserved important architectural and social histories, it has thus far only functioned as a zoning boundary that restricts urban growth and has negatively impacted the neighborhood’s long-term prosperity. This study finds that the Oldtown historic district has also played critical roles in communicating Oldtown’s enduring racial inequality and traditions of local civil rights activism, as a physical record of failed urban renewal. Community groups are reclaiming the historic district as a space to understand and transform established urban planning practices that normalize racialized poverty and craft new political identities in the present. Oldtown highlights the need for critical analysis of historic districts' influence on social and economic development, and in turn, this study draws upon the assets of historic districts to position the urban zones as sites for innovative urban policies for cooperative enterprises that address structural and racial inequality.