In the narrow valley below the Long Mynd stretch of the Shropshire Hills, Stretton-en-le-Dale was a manor comprising what were originally Saxon settlements of All Stretton, Church Stretton, and Little Stretton; Church Stretton was the central and largest, its qualifier 'Church' being first documented in 1327, although a church there is indicated by Domesday. The Strettons are believed named for their proximity to that part of Watling Street built by the Romans between Chester and Caerleon, although the Stretton stretch of Watling Street itself did not attract post-Roman settlement; in the Middle Ages this route facilitated communication with Hereford and Bristol. Of more immediate value was a road forking off Watling Street (along which the Stretton settlements were strung) and headed towards Shrewsbury, passing directly through Church Stretton, where it was crossed by another road leading east to Much Wenlock and west (after ascending the Long Mynd) to Bishop's Castle. These routes would have given the village's commercial potential a competitive advantage, and an informal market may have come into existence beside the church. The site of Church Stretton may also have been influenced by the need to place the church which served several communities in the vicinity on raised ground, less vulnerable to flooding, while a nearby brook provided a water supply.
Forfeiture of the estates of the rebellious Earl Robert de Bellesme led to Stretton being a royal manor at the time the first market (Wednesday) and fair (a single day in August) were licensed in 1214; although the sheriff was ordered to proclaim the grant and see that the market was held, there is no documentation that indicates whether it proved successful or a failure. Church Stretton's location on a major route between Shrewsbury and Hereford ought to have brought some business the way of its market. To guard the valley, Stretton, (also known as Brockhurst) Castle had been erected, probably by the king, just under a mile south of the settlement ca. 1154, and the revenues from Stretton manor were usually assigned to the castle's keeper, until the majority of Henry III, after which the manor was farmed out up to the reign of Edward II and thereafter granted to a series of lords, but most of these holders showed no inclination to develop it. A church was built, or rebuilt, at some point in the twelfth century. By mid-thirteenth century the castle had lost its strategic value and been allowed to fall to ruin, so that it is unlikely to have affected the development of a market-based settlement; but the church was enlarged around the early thirteenth century and the new size of the churchyard (about 10 x 11 perches) has given rise to speculation that it was allocated in the context of a plan for laying out burgage plots.
The churchyard was situated close, if not adjacent, to the present-day High Street stretch of the north-south through-road leading to Shrewsbury and Ludlow. The market site was probably a larger version of the present marketplace, at the north end of the High Street, where it joined the east-west through-road; the medieval marketplace may essentially have been a widened stretch of the north-south road extending from the crossroads down past the east side of the churchyard, but with parts later lost to encroachment. The initial wider stretch of the western arm of the crossroads might also have been expansion space for the fair, as it was in later centuries. Running past the west side of the churchyard, what is now Church Street was earlier known as Back Lane, a name typically given to the rear access to a series of burgages laid out in a planned fashion. Most of the settlement was on the south side of this crossroads, along the east-west arms of which ran the town's brook. Although difficult to be certain from surviving evidence, tenement plots along the east side of the High Street/marketplace and on its west side south of the church have, on the earliest maps, that long and thin look of burgages, and might represent the posited planned town, whereas the plots of less regular shape on the north and west sides of the church could represent parts of the earlier village that survived the superimposition of a planned town. Until modern times, Church Stretton underwent little expansion from its medieval form, the only pressure on land use being in the marketplace.
An urban expansion to the village settlement may have been planned and laid out when the first market was licensed, but the evidence of it is mostly topographical and it cannot be said with confidence when Church Stretton attained urban status. After having been farmed out for some years, Stretton manor returned into royal hands 1245-67 and it was in this period that a new licence was issued, for a Tuesday market, and a second fair (four days in May), in 1253, but once more the fate of the market is unknown, although the fair is evidenced in later periods and may have survived thanks to trade in livestock. That Church Stretton was being treated as a manor in its own right by 1255 and that the men of Church Stretton were organized and prosperous enough to try to hold the manor at farm themselves for three years (1258-60) may point to the existence of an urban community attempting to assert itself, but the arrangement did not continue longer. Perhaps the initial efforts, in 1214 and 1253, to develop local commerce were abortive, or perhaps the market(s) survived just on local consumption plus a portion of the business from merchants passing along its through-roads. It may be significant that we hear of ale-sellers there in 1393, and travellers were likely served by one or two taverns and inns, yet no significant medieval industry is evidenced.
The king granted the manor of Stretton to Richard Fitz-Alan, Earl of Arundel and of Surrey, in 1336 and the following year issued him with a new licence for market (Thursday) and fair (three days in September), but both remain without further mention until the post-medieval period, when Stretton's fairs are heard of again. This was the only market licence known to have been sought by that Richard Fitz-Alan, although his predecessors in the earldom had a history of such initiatives. The family's involvement with England began after the rebellion of Robert de Bellesme, when Henry I sought men he could rely on for support in the Welsh Marches and he made a Breton ally, Alan Fitz-Flaad, sheriff of Shropshire.
Alan's son William became lord of Oswestry and married the heiress of the lord of Clun. William's son, William Fitz-Alan II, issued a charter in the 1190s that founded a borough at Oswestry, for purposes of improving an existing market there, and he obtained (1204) grant of fairs for Clun and Chipping Norton (Oxfordshire). William Fitz-Alan III was succeeded by his brother, John, who married the daughter of the Aubigny earl of Arundel; John obtained grant of a fair for Oswestry (1228), but only weeks later had to defend his market at Oswestry against challenges from Shrewsbury and Montgomery, a problem resolved by altering the weekday on which Oswestry's market was held. His son and successor, John, Earl of Arundel from 1243, instituted (1253) a second fair at both Clun and Chipping Norton, having already (1250) challenged the market and fair at Knockin, six miles distant, as detrimental to his own at Oswestry, and perhaps succeeded in disabling them. John III's grandson, Edmund Fitz-Alan, who entered into the earldom only after emerging from his minority in 1306, obtained in 1311 licence for a market and fair at Ruyton-XI-towns; he married the heiress of the Earl of Surrey. It was his son Richard who, as indicated above, obtained the manor of Church Stretton and in 1337 tried to breathe new life into its commercial institutions. His like-named son would seek to develop estates acquired through the Surrey earldom, obtaining market licences for East Angmering (Sussex) in 1382 and Castle Acre (Norfolk) in 1391.
This Fitz-Alan practice of commercial development of estates was continued by later generations, although of the many commercial centres established by the Fitz-Alans, only Oswestry ever amounted to more than a small market town. Despite its advantageous position on travel routes, Church Stretton was, in the Middle Ages and afterwards, only a small market town in fact, Shropshire's smallest. This should not be taken as disparagement; such small markets were as vital to the overall network as the major provincial centres and coastal ports were, for all played complementary roles.