The “crossroads” is a recurring trope in popular and academic writing on the South Caucasus. This trope can conjure simplistic explanatory frameworks of timeless “silk road” connectivity, or of the region as a meeting point of East and West, democracy and authoritarianism, or Christianity and Islam. However, it also is evocative of the powerful ways that the movement of people, goods, and ideas across the region have shaped its past and present. In this contribution I explore how histories of migration and refugees connect the South Caucasus and the Middle East, and what these histories may tell us about the Nagorno-Karabakh conflict.