Based on a case study of a particular countryside and town in southern England—namely, the county of Wiltshire and the city of Salisbury—this record seeks to explore the changing nature of English society during the period from 1380 to 1520. It examines the influence of landscape and population on the agriculture of Wiltshire, the regional patterns of arable and pastoral farming, and the growing contrast between the large-scale mixed farming of the chalklands and the family farms of the claylands. Discussing how economic growth generated problems of its own, this study is the first to fully investigate Wiltshire’s agriculture history during the late Middle Ages, a period recognized as one of considerable change.