This thesis explores colonial geographies of Stradbally, Co. Laois, from the mid-seventeenth to the mid-nineteenth centuries, a period of profound social and physical transformation through Anglicisation. Using a tripartite methodological framework involving postcolonial theory, comparative case-studies, and geographic information systems technologies, the thesis examines colonial experiences at Stradbally within the defined historic and geographic settings of two unique landed estates. The history of the Cosby and Walsh-Kemmis estates differs in respect of family origins, modes of acquisition, and longevity of connection with Stradbally, yet are similar in having retained ownership of some of their original estates and archives to the present day. This is highly unusual in the Irish context and makes Stradbally a unique place to examine the effects of colonialism. Postcolonial theory guides this interpretation of colonial relations on past landscapes and societies at Stradbally by considering the notion of Self and Other (differences) through imaginative geographies, and the ‘civilising mission’ or ideologies of reform through improvement. The central approach uses the landed estates as the unit of analysis, enabling within them patterns of land occupation and ownership to be examined at farm and town plot level believed to be representative of the social, economic, and political relationships of landlordism. In recognition that hegemonic power is exercised to varying degrees of influence within any one region, the thesis uses two case studies within one locality to compare estate management practices and their resultant colonial experiences at a local level, thus highlighting in acute ways, the similarities, variances, and anomalies of each estate, which contributes to both the historiography of landed estates, and their role in the colonial history of Ireland.