The familiar image of Cheltenham, a large and prosperous former spa town, world-famous on account of its Georgian and Regency architecture, its festivals and educational establishments, masks an earlier history. While numerous descriptions of the town have been published over the years, most say little about the many centuries of its existence before the 1740s, when it began to develop as a fashionable resort. This is the fullest account ever attempted to chronicle those centuries, from the late Saxon period until the 18th century. In this period, Cheltenham developed into a successful small town, ranged along a single main street, with the market and trades serving not only its own needs but also those of the surrounding countryside. It draws on a range of documentary sources preserved in local and national archives, many of them never examined in detail before. It therefore helps to explain the foundations upon which present-day Cheltenham was constructed.