With this paper, I will attempt to shift the focus of the Counterculture of the 1960s and1970s from the Global North and examine how it affected cultural norms and perceptions in theGlobal South. My presentation will look at the ‘Hippie Trail’, a colloquial way to refer to a travelroute taken by many European and North-American youths to the East at the height of thecounterculture movement. The East served as an allegory of varying meanings but travelers oftencame by land from a European center like London and Amsterdam to anywhere relatively east,often ending in South and Southeast Asia. In this presentation, I try to understand the perceptionsof the trail in the Bengali cultural milieu through the literary representation in Satyajit Ray’sdetective Novel, Gangtok-e-Gondogol.