Walking is a mode of perceiving the city which also contributes to health and social benefits. This paper studies the influence of the socio-cultural aspects on the practice of walking and the meaning of walkscapes in Riyadh, one of the most auto-dependent and gender-segregated cities on the Arab Peninsula, where socio-cultural values and restrictions regulate men and women’s use and access to public spaces. The methodology used is a combination of movement tracking data using GPS technology and map-based workshops where participants can reflect on their walking behaviour and spatial preferences. The results of mapping where the respondents walk show a city consisting of gender-specific walkscapes. Indoor environments, such as shopping malls, function as ‘urban shelters’ for women, so they use such spaces for walking. On the other hand, young men mainly walk in urban streets, which provide greater opportunities for gender interaction. However, streets are socially conceived as men’s walkscapes, which limits women’s presence, especially at certain times of the day. This paper reveals how walking experience, tempo-rhythm, sense of place and range of walkscapes are not only determined by ‘universal’ spatial qualities but also influenced by socio-cultural settings.