The first industrial heritage site in Asia to be recognised as a World Heritage Site (WHS), the Darjeeling Himalayan Railway (DHR), (now part of the serial nomination of Mountain Railways of India), finds itself at the intersection of the past and the future. The OUV of the site describes it as an engineering marvel, the DHR is not just the narrow-gauge railway but also the experience of the journey through the myriad landscapes it traverses over its 88 km length. Since its construction in 1881, the DHR has been the lifeline for the region, serving as the primary freight corridor for the tea gardens, chugging the children from the boarding schools up and down as well as sustaining several local communities employed in running the railway. Until the 1930s, the DHR had the monopoly of transporting goods and passengers, however the loss of commercial activity on the line as well as the relegation of the line as a purely tourist Railway has had a severe impact on the socio-economic activities within the region. The threat of loss and nostalgia of the toy train, led to a community campaign leading to the inscription of the site on World Heritage List in 1999. The last 20 years, post inscription have highlighted the major gaps between the understanding of the experts and stakeholders endangering the site itself. The DHR isn’t derelict, it is home to about 2,200,000 people with a thriving tourism and tea industry. With no formal legislation to protect cultural landscapes or industrial heritage sites in India, the primary challenge is the definition and management of the world heritage site and its buffer zone. The absence of a clear management plan between the stakeholders as well as overlapping jurisdiction and mandates between the various levels of governments have further complicated the issue. This grey area has been exploited by the local people for constructing unauthorised housing and tourism related development in what should have been earmarked as the buffer zone, severely compromising the key views and vistas. The State-owned Indian Railways, the primary custodians of the site have been driven by the nostalgia of the toy train in attracting more high paying tourists. This has encouraged policies for its commodification while excluding the local community. The dwindling number of trained and skills workers in repair and maintenance of steam engines, due to retirement of the old staff and no new recruitment has led to a lacuna in human resources for properly running the railway. A change in the federal policy with respect to local recruitment within the Railway has left many youths unemployed in the region. The functional and frugal buildings of the DHR are not considered to be of any heritage value by the Railways, there has been a colossal loss of artefacts and machinery on the premise of it being “too ordinary”. Negligible funding or expertise for heritage conservation have led to misguided conservation efforts of many of the stations being stripped and converted into museums. Who then is responsible for articulating the heritage values of a site the experts or the local community? Is world heritage protection contrary to the continuity and evolution of the site? How can industrial heritage be used to serve the local community? With the State being cash trapped who can then take responsibility for sustainable development of industrial landscapes? This paper questions the purpose of industrial heritage and identifies the bottlenecks for community led development in the Indian context.