Church Stretton began as an Anglo-Saxon settlement owned by the Saxon Earls of Mercia, who founded the Church of St. Lawrence which not only still stands at its original location but contains many of its early features including a Norman nave and a rare carved fertility symbol. The settlement was first established near Watling Street, a road built by the Romans that ran from Uriconium via the Stretton Gap to Gloucester.
Following the Norman conquest, Church Stretton was given to the Norman Earl of Shrewsbury, Roger de Montgomery. The king retook control of the manor, however, in 1102, after the death of Montgomery and the rebellion of Earl Robert de Belesme. At the beginning of the 14th century, King Edward III granted the manor to Earl of Arundel, Richard Fitzalan, and Church Stretton stayed with his family until 1579. Another family that held the manor for a substantial period of time was the Tynnes of Longleat who had it from 1635 to 1802.
For the majority of its history, Church Stretton was a rural market town with its first market initiated in 1214 by King John and later established by a charter granted by Edward III who changed the day the market was held from a Wednesday to a Thursday. In addition to the weekly market that is still held in Church Stretton, there were 6 annual fairs for the sale of sheep and ponies and the hire of domestic servants and farm laborers.
Two historical events changed the face of Church Stretton. The first was a fire in 1593 that burnt down a great deal of the town. Many of the surviving half-timbered town center buildings are from this period. The second was the arrival of the railway in 1852 which brought the town’s first real visitors who dubbed the area ‘Little Switzerland’ for its landscape and helped shape its reputation as an area beneficial to health.