In the neighbourhoods and public spaces of York, young people walked out together, congregated in the streets, and paraded up and down Coney Street on the ‘monkey run’. This thesis examines these sites of leisure and courtship; the streets, public and neighbourhood spaces of the city, and questions how the young working class of York engaged with their environment through a detailed study in the forty year period between 1880 and 1920. It considers how young working people met and socialised in different parts of the city, what these spaces meant to the young people of York, and how that meaning was conveyed, contested and controlled. While recent historical work has begun to explore how the meanings, experiences and representations of youth and young people have changed over time, highlighting the importance of both leisure and courtship as distinctive features of youth, the ways in which young people have engaged with their environment has received much less attention. Yet, without an understanding of how young people interacted and engaged with their environment we are left with an incomplete picture of working-class youth culture at a time when young people were experiencing increasing opportunities for leisure and sociability. This thesis fills this gap in the literature by examining how young men and women used, experienced and shaped their environment of late nineteenth and early twentieth century York. Studying the young working class of York through the prism of space provides valuable insights into everyday life, and reveals how spaces were both shaped by, and help shape, the social interactions of the young working class of the city. Exploring the relationship between the young working class and urban space, this thesis argues for a sensitive reappraisal of working-class youth at the turn of the twentieth century.