Recent scholarship on historical welfare development in Sub‐Saharan Africa has uncovered long‐term trends in standards of living. How the majority of rural dwellers fared, however, remains largely elusive. This study develops a new approach to reconstruct rural living standards in a historical context. It builds upon a well‐established real wage literature, but moves beyond it to capture rural realities, employing sub‐national rural survey, census, and price data. The approach is applied to a case study of colonial and early post‐colonial Uganda (1915–70). The case study yields a number of findings. While the expanding smallholder‐based cash crop sector established itself as the backbone of Uganda's colonial economy, farm characteristics remained largely stagnant after the initial adoption of cash crops. Smallholders maintained living standards well above subsistence level, and while the profitability of cash crops was low, their cultivation provided a reliable source of cash income. Around the time of decolonization, unskilled wages rose rapidly while farm incomes lagged behind. As a result, an urban–rural income reversal took place. The study also reveals considerable differences within Uganda. Smallholders in Uganda's banana regions required fewer labour inputs to maintain a farm income than their grain‐farming counterparts, creating opportunities for additional income generation and livelihood diversification.