This article is an attempt to analyse the link between the condition of city environment and availability of water in Darjeeling city. Darjeeling, located in the Eastern Himalayan Region of India, is such a city which faces acute water scarcity in most part of the year, except during monsoon. The city cannot use ground water directly, and there is no river as source of water as well. It only uses spring water and rain water. The climatic condition and local environmental conditions have higher control over the availability of daily water. This article analyses the city’s 100-year climatic conditions as well as the condition of vegetation cover and built-up areas using NDVI and BUI methods, respectively. The present study explores that the deterioration of natural environmental conditions and increasing demand from both the permanent population and transitory population accelerate the intensity of water scarcity. Measuring the fluctuation of discharge (during pre-monsoon and post-monsoon period), the paper discusses how except in monsoon, most of the spring’s discharge gets reduced and increases the level of water stress in the city. Using quantitative methods, this empirical study explores that the loss of vegetation and haphazard constructions have enormous impact on the fragile hill ecosystem and reduce the rate of infiltration of water in the sub-surface zones, thus reducing the discharge ultimately. Therefore, the study recommends immediate actions to protect the city environment and to revive those springs for the city’s water security.