The concept of 'imaginative geography', first used by Edward Said in 1978, has been widely recognized by human geographers. This chapter discusses how regions and regionality were approached by the literary geographers of the 1960s and how imagining regions is ultimately a matter of someone's power to imagine something on behalf of someone else. It also discusses how this has been utilized by critical literary geographers, and finally how regions and narrativity are connected. From the viewpoint of literary geography, Edward Said's approach is particularly interesting since he considers literature as one of the key practices through which the imaginative geography of Orientalism has been constructed. The history of socially critical approaches in literary geography goes back to the 1980s, starting as criticism of humanistic geography. Through imagination and writing regions attain their territorial shape, and turn into administrative units or units around which human history and heritage become narrativized and storied.