In this chapter, I examine the connections between regions and cultural representation. My overall aim is to demonstrate the tensions that can exist between more cultural, and more economic or political forms of regionalism. Drawing on ongoing fieldwork conducted within the region of Wales in the UK, I problematise the conception of cultural regionalism and show that it is far from being a unitary or homogeneous thing, with many different cultural regions existing or being promoted. I contend that the relationship between politically or territorially defined regions and more culturally defined regions is complex. They are, undoubtedly, sometimes in conflict with one another but, at certain times, they can complement and reinforce one another. I conclude the chapter by discussing some of the potential challenges facing cultural regions and potential ways of addressing them.