Rural communities in the United States have faced mounting pressure to develop their local economies in ways that threaten their historic agrarian landscapes and cultural practices. However, these communities are often wary of, if not hostile to, top–down approaches to historic preservation and landscape conservation. Community-engaged heritage protection strategies shift the focus from managing cultural and natural heritage as discrete resources to envisioning heritage and its protection as a form of community development. This paper presents a case study from rural New England in which the intergenerational sharing of narratives about heritage landscapes moves beyond simply commemorating the past, to contributing to the present and future welfare of community members. In this case, heritage narratives shed light on residents’ changed relationships toward their land and each other, while also revitalizing a sense of a collective past and, more importantly, a shared future.