This chapter looks into the changing dynamics of adolescent girls’ migration in the Horn of Africa, with a particular focus on movement of adolescent girls and young women from Ethiopia and Eritrea. It is based on ethnographic research in Ethiopia and Sudan, and focuses on the increased independent mobility both internal and across borders of adolescent girls and young women. While for some of the young women internal or international migration is motivated by the need to secure economic security for their families, or escape war or authoritarian regimes, there are also other factors that inspire their decisions to migrate. Aspirations and desires of moving elsewhere shape the experiences of and the different transitions associated with one’s life course. This chapter extends the debate about the reasons for girls’ migration beyond poverty and human rights abuses. It feeds into wider discussions about gender, migration and generation within the region and contributes to the debates on children and young people’s mobility by showing the footprints of agency and their space for self-assertion.