People have lived in the Stretton Gap (or Dale) for thousands of years; an Iron Age hillfort on Caer Caradoc overlooks the town.
The name "Stretton" is derived from the Old English words stræt meaning "Roman road" and tun meaning "settlement"; a Roman road, Watling Street runs through the Stretton Gap, though the town (and adjacent settlements) were not historically located on this road – during the "Dark Ages" the settlements grew a short distance away from the old thoroughfare, for defensive purposes.
Today the modern A49 road, which was constructed on its current alignment through the Stretton Gap in the late 1930s, runs along a similar course to the Roman Road.
The Roman road was historically known as Botte Street.

The settlements of Little Stretton, Church Stretton and All Stretton (until the late 19th century regarded as separate townships) formed the manor of Stretton or Stretton-en-le-Dale.
The Domesday Book of 1086 recorded 35 households and a mill in the manor.
Church Stretton became the largest of the settlements, with the manor's parish church and market located there, and being where Bristol Road had a junction with the road to Much Wenlock and the Burway – a route over the Long Mynd.
At the time of the Domesday Book, the manor came under the hundred of Culvestan, a Saxon hundred that was amalgamated during the reign of Henry I — the Strettons then came within the upper division of the hundred of Munslow.

The town was first granted a market charter by King John in 1214, for a weekly market on Wednesdays, but by 1253 the market day had changed to Tuesdays.
In 1337 a new charter was granted by Edward III and it authorised a weekly market to be held on Thursdays.
The market is still held every Thursday, in the square on the High Street, which has been the town's market place since the 13th century.
Much of the town was destroyed by fire in 1593 and many of the present half timbered buildings in the town centre date from the time of the rebuilding.

The High Street was for many centuries known instead as the Bristol Road, being the road from Shrewsbury to Bristol.
It was once a much wider street within the town, with the churchyard of St Laurence bordering directly onto the street.
Over time buildings were erected on the street, in a similar fashion to other English market towns, such as in Ludlow.
The High Street, which is a narrow street, is effectively only the eastern side of the original Bristol Road thoroughfare through the town.
It was made more open when the old market hall was demolished to form the present town square.
People have lived in the Stretton Gap (or Dale) for thousands of years; an Iron Age hillfort on Caer Caradoc overlooks the town. The name "Stretton" is derived from the Old English words stræt meaning "Roman road" and tun meaning "settlement"; a Roman road, Watling Street runs through the Stretton Gap, though the town (and adjacent settlements) were not historically located on this road – during the "Dark Ages" the settlements grew a short distance away from the old thoroughfare, for defensive purposes. Today the modern A49 road, which was constructed on its current alignment through the Stretton Gap in the late 1930s, runs along a similar course to the Roman Road. The Roman road was historically known as Botte Street.
The settlements of Little Stretton, Church Stretton and All Stretton (until the late 19th century regarded as separate townships) formed the manor of Stretton or Stretton-en-le-Dale. The Domesday Book of 1086 recorded 35 households and a mill in the manor. Church Stretton became the largest of the settlements, with the manor's parish church and market located there, and being where Bristol Road had a junction with the road to Much Wenlock and the Burway – a route over the Long Mynd. At the time of the Domesday Book, the manor came under the hundred of Culvestan, a Saxon hundred that was amalgamated during the reign of Henry I — the Strettons then came within the upper division of the hundred of Munslow.
The town was first granted a market charter by King John in 1214, for a weekly market on Wednesdays, but by 1253 the market day had changed to Tuesdays. In 1337 a new charter was granted by Edward III and it authorised a weekly market to be held on Thursdays. The market is still held every Thursday, in the square on the High Street, which has been the town's market place since the 13th century. Much of the town was destroyed by fire in 1593 and many of the present half timbered buildings in the town centre date from the time of the rebuilding.
The High Street was for many centuries known instead as the Bristol Road, being the road from Shrewsbury to Bristol. It was once a much wider street within the town, with the churchyard of St Laurence bordering directly onto the street. Over time buildings were erected on the street, in a similar fashion to other English market towns, such as in Ludlow. The High Street, which is a narrow street, is effectively only the eastern side of the original Bristol Road thoroughfare through the town. It was made more open when the old market hall was demolished to form the present town square.
Church Stretton