This chapter interrogates the historical trajectories of the Himalayan subjects named as Lepchas, Bhutias, Gurkhas, and Sherpas, who played a crucial role in producing Darjeeling as a vibrant mountain space for circulation, enterprise, and culture. The establishment of an imperial hill station resort led to numerous and novel—often unanticipated—labouring and service openings that the indigenous peoples of the Eastern Himalayan borderlands parleyed into new possibilities for livelihood and mobility, albeit with varying degrees of success. The chapter examines how the complicated negotiations of indigenous groups with the racially determined practices of tea plantations, botanical and mountaineering expeditions, mission stations, and military recruitment shaped new modernistic identities and were constitutive of Darjeeling as a trans-Himalayan space defined by mobile lives and cross-cultural encounters which in turn it helped constitute.