Planning and development activities in peripheral or non-urban spaces have undergone profound changes under the influence of geographic information systems (GIS) and spatial data analysis in the last two decades. This chapter investigates the challenges (methodological and practical) in the implementation of GIS to economic and planning applications in the peripheral regions (the developing and the developed world) in the context of society’s transition from paper maps to digital geographic information. This research is significant since it is premised that implementation of GIS itself is ‘contextual’ and involves an appreciation of the human conditions(s) experienced in different places. The findings of this chapter’s investigations as a result of review of literature is that much of the challenges lie not as much in how to introduce the technology to recalcitrant institutions in the peripheral regions of the world but in managing the availability of a mature technology and empowering the people while embedding the technology through participatory GIS in the context of different places. In other words the challenges are not simply technical but they are also political in the broadest sense of the word.