Through time, Hospitalfield in Arbroath, Scotland, served as a pilgrim hospice, private home, art school, and artist residency centre. In the 20th century, its art school and residency programme enabled hundreds of artists to live, work, and learn within a unique educational environment. Despite its wide-reaching impact, Hospitalfield has remained an ethereal presence within scholarship. This thesis presents the first investigation of its significance to the development of 20th-century Scottish art. Part 1 examines Hospitalfield's importance as a place where artists, throughout the 20 th century, encountered new influences, formed communities, responded to the landscape, and developed their own practices. Its analyses provide new insight into the work and careers of well-known Scottish artists and introduce significant works by their lesser known contemporaries. It also explores the impact of Hospitalfield's institutional change upon the student experience and its relationship to broader trends in art and education. Part 2 focuses on the art and influence of Hospitalfield's resident 'Warden', James Cowie , (Warden from 1935-1948) and Ian Fleming (Warden from 1948-1954), arguing that Hospitalfield contributed to the development of Scottish art by enabling the evolution of Cowie's and Fleming's artwork and the dissemination of their influences. It presents new analyses of Cowie's and Fleming's work and contextualises their bodies of work within the painting culture of Scotland and beyond and traces how aspects of the Wardens' practices influenced multiple generations of artists. Both parts were informed by archival material, secondary sources, and oral history interviews conducted during the research process and archived in the Elphinstone Institute, University of Aberdeen for future educational use. In accordance with the research's funding arrangement between the Hospitalfield Alumni Association and the University of Aberdeen, Part 1 was written to be accessible to a generalist audience, while Part 2 is in an academic style.