This article examines the semiotic operations by which ‘heritage’ is represented and serves as a commodity in a tourism project in southwest Virginia known as The Crooked Road: Virginia’s Heritage Music Trail. I examine the methods and stakes of representing musical ‘heritage’, presenting it for consumption, and relying on it as a regional economic engine. Central to these methods and stakes is a representation of ‘heritage’ as an inalienable possession of a place, of its people and landscape. This representation in turn indexes a paradox of folk authenticity, where a musical form that is supposed to inhabit the last commercialism-free domain of ‘heritage’ is simultaneously called upon, according to the paradigm of ‘asset-based development’, to generate regional revenue. In this process the folk culture that is supposed to dwell in the contoured landscape of ethnomimetic transmission and vernacular expression has to register on the plane of potentially infinite equivalences comprising exchange-value, where, metaphorically at least, the ‘crooked’ road, valued for its use to the tourist as such, is straightened for the sake of exchange.