This article focuses on the stigmatization of place and resultant effects on redevelopment in a community once dependent on the pulp and paper industry, yet located in a high-amenity, recreation-dependent region. On the basis of historical environmental conditions, the community became known regionally as a polluted and undesirable place and this negative image has posed a number of challenges to redevelopment efforts. Today, tourism-based development appears constrained, symbolically and materially tied to the local ecohistorical context. I employ an ethnographic approach to first elaborate a key element of local place character—environmental stigma—and then show how it has shaped the course of redevelopment there. Though originally centered on environmental conditions, the community’s place stigma has become more complex, incorporating a set of negative community effects common to deindustrialization. I analyze the effects of long-term and diffuse processes of environmental harm and decay, and show how such stigma can present subtle yet real obstacles to redevelopment. I demonstrate how place matters for the course of community change, emphasizing how dynamics of place can run counter to what is expected when a community fits the description of a high-amenity community ostensibly positioned to undergo a new phase of amenity-based growth.