This article focuses on the historical trajectories of women's empowerment in Sierra Leone, taking three entry‐points as a means of exploring the dynamics of change over the pre‐conflict, conflict and post‐conflict periods: voice and political participation; work and economic participation; and bodily integrity. Looking at pathways of empowerment in pre‐conflict Sierra Leone, at experiences of women during the time of conflict over the course of a long and brutal civil war from 1991–2002, and at post‐conflict possibilities, the article highlights some of the changes that have taken place in women's lives and the avenues that are opening up in Sierra Leone in a time of peace. It suggests that understanding women's pathways of empowerment in Sierra Leone calls for closer attention to be paid to the dynamics of conflict and post‐conflict reconstruction, and to the significance of context in shaping constraints and opportunities.