This article examines the relationship between scale of observation and landform features and their representation in map form. The research is premised on the idea that large scale features are defined by the smaller features that comprise them (that mountain ranges are a collection of clustered yet individually identifiable mountains or hills). In preference to subjective selection of the higher order features, we propose a methodology for automatically discerning mountain ranges as well as the smaller hills that constitute them. A mountainous region can be defined by its prominence (relative height among surrounding features) and various morphological characteristics including the variability in morphology. The algorithm presented here uses derivatives of elevation and the density of morphological properties in order to automatically identify individual hills or mountains and ranges together with their extents. Being able to create generalised views of landscape morphology is considered to be part of the model generalisation process and is an essential prerequisite to spatial query and to the cartographic portrayal of these features at a range of scales (levels of detail). For the purposes of evaluation the algorithm was applied to the hills around Edinburgh city and the hills and ranges around Fort William, Scotland. The research reflects on the challenge of defining the subjective nature of what is a ‘hill’ or a ‘mountain’, but reminds us that a map seeks to capture the essence and characteristic form of the landscape – something that is necessarily fuzzy and scale dependent.