Space syntax is a theory and set of tools and techniques for the analysis of spatial configurations. It was developed at UCL in the late 1970s, as an approach to understanding human spatial organisation and to help architects and urban designers to simulate the likely social consequences of their projects. The fundamental proposition of space syntax is that a building or place can be broken down into spatial components, so that an analysis of the interrelations of the components will yield information about the pattern of space that is meaningful and functionally relevant. Over the past thirty years, space syntax has been successfully applied to resolve problems as diverse as master planning entire cities or revealing the imprint of culture in domestic settings. With this in mind, this paper will explore opportunities and challenges of taking a syntactic approach to the spatial analysis of landscape. To the extent that people avoid walking through landscapes in which they feel apprehensive, understanding the spatial characteristics of such environments should enable landscape designers to create vital landscapes that support healthy lifestyles and avoid those conditions where people may feel insecure. The paper will focus on how the tools/techniques of space syntax can be adapted to understand the circumstances in which people feel motivated to explore their local landscape and the spatial factors that may deter people from incorporating walking into their everyday routines.