This paper outlines and analyses efforts to critically engage with "heritage" through the development and responses to a series of undergraduate residential fieldwork trips held in the North Coast of Jamaica. The ways in which we read heritage through varied "texts"--specifically, material landscapes, guided heritage tours, visual imagery and creative writing--and how these readings are couched within changing emotional geographies are analysed in relation to specific field-based sites. The study highlights the dynamic nature of heritage landscapes and the creative ways in which they can be understood and represented through diverse forms of engagement and assessment.