Walkability provides a foundation for a sustainable city. The effectiveness of walkability is linked with socio- economic, environmental and psychological issues. Walkability provides safety, security and comfort for the city dwellers while traveling as well as cleanliness and transparence in mobility by reducing street congestion, street pollutions, vehicle fuel cost and road fatalities. Present motorization and urbanization in Indian cities, resulting in reduced mobility and increasing hazards, has thrown a challenge to the planners and decision makers in favor of conversion of motorized cities to walkable cities. In this paper, the prospects for walkability and related issues has been analyzed and discussed for Siliguri city. Siliguri, a medium sized city of West Bengal, India has emerged as a major urban center and acts as Gateway to the entire north-eastern states of India. Planners fear that the population of Siliguri may reach up to 2 million by 2025. As Siliguri is not a planned city, it has been experiencing problems in meeting present demand with its social and physical infrastructure. The streets of Siliguri is almost choked by mixed traffic, usually paratransits and personalized two/four wheelers, slow moving vans, dense urban corridors and existence of busy commercial set ups along major roads. The rapid motorization and increasing level of economic status of the city dwellers has put immense pressure on transportation system of the town resulting in high level of congestion and fatalities. Thus, keeping many aspects as constraints, there is an urgent need to identify the prospects of walkability in the city for sustenance. In this paper, an effort has been made to identify possibilities of transforming Siliguri into a walkable city where more people will opt for walking as their first choice for short trips and to make longer distance trips using a combination of walking and public transport instead of using personal automated vehicles. The research finally reveals that there are ample opportunities to make Siliguri walkable, however, detail investigations and quantification of walkability indices are required for implementation.