Cartographic reason is ocular centric, is expansive in nature, and tries to create an integrated one world view which is a forerunner to today’s globalisation. Likewise, it often functions with a high-altitude aerial panopticon-like point of view integrating it with finer in situ minutiae leading to stereotypical essentialisations. A colonial gaze is primarily a cartographic gaze. This line of argument is fruitful to pursue because it helps us understand and critique spatial matrices constituted by the forces of colonialism, namely imperialism and nationalism. This chapter goes on to elaborate imaginations and machinations involved in cartographic surveys undertaken in the British Isles before its final evolution as a nation. Important among these projects, were General Roy’s Military Survey of Scotland and the mapping of estates in Ireland. The same were seamlessly integrated with the popular cultural production in the metropolis so that not only a map literacy was generated, but there was a general euphoria about new scientific methods of map making.