The First Land Utilisation Survey of Great Britain (LUSGB), coordinated in the 1930s and 1940s by Professor L. Dudley Stamp, is regarded as one of the most pre-eminent surveys of land utilisation in Britain. This paper considers techniques and methodological challenges in converting the wealth of information within the survey into digital vector format. The first steps of this process involve high resolution scanning of the map types of the LUSGB, followed by georeferencing. Supervised classification image processing techniques are then used in order to create a set of signatures from which, following clean up processes, subsequent vectorisation can take place. The paper then explores the resulting digital data from this semi-automated procedure for consistency in order to assess both the proposed method’s accuracy for digitalisation of historic land change, as well as the respective accuracy of each map type of the original LUSGB. In particular, this paper examines the data produced from the one and ten-inch map series and also examines individual colour layer maps produced as part of the printing process. The paper concludes by reflecting on the potential of the semi-automated approach experimented with as well, as the avenues for future research in this area.