There is a growing need to adapt a geostrategic perspective to assess the mutual benefits of linking India?s northeast and Southeast Asia. It is a fact that the Northeast India is a resource rich, strategically positioned area which also shares an extensive international boundary of about 5500 km with India?s neighbours. The region holds great significance in terms of India?s connectivity and infrastructural ventures with Southeast and East Asian nations. Reopening and developing the historical Stilwell, originally known Ledo road, in the Northeast is of strategic importance. This essay is an effort to unravel the rationale, opportunities and challenges and the future of reopening of the Stilwell Road for being a potential gateway to Southeast Asia and East Asia.