Historic Chestertown, Maryland, is one of the oldest existing communities in the state of Maryland. Strategically situated along the Chester River, this town—like many others on the Delmarva Peninsula—is at risk to external forces of climate change and sea level rise which threaten to inundate and displace the town. Facing an uncertain future due to climate change and other socio-economic factors, Chestertown possesses the opportunity of challenging the status quo and raises the question can the concept of community be reimagined to address the severity of climate change and sea level rise while fostering a positive relationship to the environment? Observations to historic patterns of settlement, resilient design strategies, and building construction methodologies have been analyzed and applied to help protect the historic town while fostering an environmentally conscious community model. This model serves as a critique to previous settlements and current development proposals for the town, challenging the need to prioritize natural ecology over the built environment.