Populaces are prominent indicators of livability in creating ‘street life’ for cities and public spaces. Evaluating people’s experiences is significant in creating a city liveliness and urban heritage trail. The exploration of design strategies that could allow them to integrated and connected with other spaces in the context of city and heritage as well as creating a social life among them. The measuring variables are people’s experience on the spaces; thus, create the pattern of behavior, which cause spaces liveliness, using Kuala Lumpur Heritage Trail as an example of pedestrian priority streets, city environment and heritage value. The aim of this research is to evaluate people’s experiences and analyze their behavior towards the urban street design within cities environment and Malaysia heritage values. The analyzed review comprising on the livability of the street in the context of interrelation between behavioral patter of people and the preferences of urban heritage. Hence, this paper will give an understanding of how people experiences the presence of urban streets and heritage values, thus, bringing liveliness to the streets.