In the nineteenth century the word “leisure” came to represent not just free time but a social sphere of human activity shaped by work, religion, gender and social class. As the welfare economist John Hobson observed, leisure evolved as part of the organic life of society. This chapter explores the progressive historical association of leisure with welfare. The origins of modern debate on leisure lie in Jeremy Bentham’s association of happiness with hedonic pleasure. John Stuart Mill, however, saw leisure as a field of self-realisation and mental cultivation. The organisation of leisure was distributed across differing contexts. While Bentham’s hedonic leisure reflected the laws of political economy and commerce, eudaimonic uses of leisure found in mutual societies, co-operation and voluntary action focused on the enhancement of working-class welfare.