This paper applies Kevin Lynch's famous thesis of legibility to the main street of Singapore—Orchard Road. It is primarily concerned with three issues. How legible is Orchard Road in the eyes of Singaporeans? Who find Orchard Road legible? If Orchard Road is legible to Singaporeans, why is it so? Based upon a combination of comprehensive questionnaire survey of Singaporeans and personal interviews with residents and businessmen operating in Orchard Road, this paper argues that the landscape of Orchard Road, known as the Orchardscape in this paper, is very legible to most Singaporeans. Its legibility is particularly prominent among those with higher education and higher income levels. There is also a distance-decay effect in the Singaporean cognition of the Orchardscape. The legibility of the Orchardscape is explained in relation to the personal and cultural background of individual Singaporeans and landscape cues. We argue that both sets of factors must be taken into consideration in understanding the image of the city. Some practical implications for future city design and planning are offered in the concluding section of the paper.