Drayton is situated near the Shropshire/Staffordshire border, on the lightly settled slope of the Tern Valley, just north of a large loop in that river; the Tern flows south-west to meet with the Severn but was not itself navigable for large vessels, yet the site of Drayton may have been a crossing-point of the Tern. The manor's holder at the time of Domesday, William Pantulf, subsequently gave it and its church as a gift to the monks of Noron, whose house he had founded as a cell of the Norman abbey of St. Evreuil. What would become Market Drayton was then only a modest settlement, on the edge of the manor, and was sometimes referred to as Drayton in Hales; yet Domesday identifies a priest there, implying a church, and some growth during the twelfth century is suggested by the fact that in the thirteenth it would be distinguished as Magna Drayton from another part of the manor, Little Drayton. The name 'Market Drayton' is not documented before the sixteenth century. Noron Abbey's proctor in England made, probably in the early thirteenth century, a perpetual lease of it to the Cistercian Abbey of Combermere (founded in the 1130s), whose community had accumulated experience of developing an isolated site in Cheshire; this abbey had already acquired some lands in the neighbourhood of Drayton and later acquired full ownership of Drayton itself. The size of the settlement of Great Drayton at this time is hard to judge; it is difficult to take seriously a statement by a jury in 1292 that there were only only half a dozen cottages in the settlement, but perhaps this referred only to the non-urban component.
It was to Abbot Simon and his monks, then, that the king issued a licence, in 1245, for a Wednesday market (still held today) and September fair (at the festival of the Nativity of the Virgin Mary) at Great Drayton; the abbot had taken advantage of a royal visit to Combermere to make the request of his guest. Presumably that abbot, or a successor, purposed to develop a market town there, for we hear of burgages and a market stall there being granted by the abbot in the late thirteenth century, and in 1292 Drayton is referred to as a 'new borough' under lordship of the abbot. The latter reference was in the context of a quo warranto proceeding requiring the abbot to prove his right to fair, market, and other privileges at Drayton; the market had been mentioned at the hundredal enquiries of 1255, but it was still fresh in memory then that the abbot had royal licence for it. The abbot now submitted this licence in evidence and the challenge to fair and market was dismissed; but a jury stated that the other privileges (including a court exercising hundredal jurisdiction) had been usurped from the king about a decade after the market grant, so that it was adjudged the abbey might keep those privileges for an annual farm, plus arrears. It was perhaps to address this issue, as well as bring additional benefits to the new town, that in 1331 the abbot presented, for Edward III's inspection and confirmation, an enlarged and presumably spurious version of the 1245 grant, which also purported to grant the abbey, among other things, independence of any other hundred or county court, and exemption of tolls throughout the realm. The town seems to represent an extension northwards from the older village, and was one of the earliest initiatives of the Cistercians in England to found a market town.
It was in large part the burgesses' subjection to the abbot, stifling self-determination and the ambitious initiatives that tend to arise from the same, which prevented the town from growing much. Nonetheless, by the 1380s we hear of the hall of a socio-religious gild and of shops there, as well as a 'bulkhouse' in the marketplace (perhaps a storehouse or the precursor of a market hall), and leather-workers seem to represent the principal local industry one lane was known as Glovers Lane in the fourteenth century although cloth-workers and food services are also evidenced. But there is no sign of a borough court, and it seems the abbey kept local administration carefully under its thumb and in its own hall, heard of in the late fourteenth century. Even in the post-medieval period Drayton remained only a small market town.
But perhaps this was all the abbey wanted: a source of modest annual income; an untroublesome community of burgesses; a market able to supply many of the material goods the monks needed, less than ten miles distant from the abbey, so that a return trip might be made within a day, without the expense of employing mercantile agents or sending monks out on overnight journeys; and a market and fair through which some of the raw materials produced on abbey lands might be sold without incurring tolls. Those materials perhaps included salt from Nantwich, in which the abbey held a share, while Combermere was also one of the first monastic houses in Cheshire to take up sheep-farming (before the mid-thirteenth century); by 1300 some of its wool was being marketed through Boston's fair. The abbey is known to have had one of its granges in Drayton. Michael Fradley ["Monastic enterprise in town and countryside: two case studies from north-east Shropshire," Landscape History, vol.28 (2006), p.10] has noted that during the same period that the market town was founded, Combermere was establishing on its lands in the vicinity a number grange farms operated directly by the abbey, and he sees the two initiatives as part of a single strategy to boost abbey revenues by, on the one hand, having a market through which its produce could be sold and, on the other, by growing a local population that would, as consumers and manufacturers, purchase some of that produce.
However, such a commercial resource at Drayton was no shield against poor abbatial administration, which slowly mired the abbey prosperous in its first century of existence in debt, first signalled in the 1250s, to the point that by 1275 the Lord Chancellor, Bishop Robert Burnell, had to step in and take over abbey management, placing it under royal protection from its creditors, and providing it with an influx of cash by buying some of its lands himself. Its impoverished state persisted through the Late Middle Ages and there would be other periods when royal custodians took over. Poor fiscal management and contentious policies of the abbots were partly to blame for the problems; one of several feuds or conflicts was with the Abbey of St. Evreuil (mother-house of Noron) over the church at Drayton, and resulted (1281) in the abbot and six monks being excommunicated when they stood guard at the church to prevent the Archbishop of Canterbury from entering. After the Black Death the abbey gained a reputation for indiscipline and even criminous behaviour on the part of some abbots and monks.
The market established at Great Drayton must have benefited at first from the lack of competitive institutions, both in its part of Shropshire and in the western part of neighbouring Staffordshire Eccleshall, the nearest, being ten miles off, though Shrewsbury was only fifteen miles to the south-west. Drayton's were the only market and fair known to belong to tCombemere abbey, although its daughter house of Dieulacres Abbey originally established at Poulton, after it moved to Leek (Staffs.) attracted settlement for which the Earl of Chester obtained a market licence in 1207, then by charter founded a borough there at the same time or within a few years though the abbot later claimed the earl had granted the whole to the abbey. As the abbey sought, in the early fourteenth century, to overcome its financial difficulties, it obtained licence for a Friday market and a second fair; yet at the same time it was leasing out to Drayton residents, on terms more favourable to the lessees than to the abbey, the grange farms in the vicinity of the town, and so losing the synergistic advantages of its original strategy.
The church of St. Mary, which has some fabric dating back to the twelfth century, although much was rebuilt in the fourteenth, is assumed to have been the focus of settlement at Drayton in the eleventh century. It faced onto the (future) High Street section of an east-west through-road, flanked by two lesser streets one being Church Street running south off the through-road. The market was likely held in a funnel-shaped stretch of the High Street a little further west than the church; the length of this marketplace may perhaps have been extended when the new town was laid out. It was probably along either side of the marketplace where the first burgage plots were laid out, with subsequent expansion (continuing into the post-medieval period) further along the through-road in both directions and perhaps not until the Late Middle Ages into secondary streets leading off the marketplace. At some period, perhaps beginning in the Late Middle Ages but mostly post-medieval, encroachment covered much of the central area of the marketplace, leaving streets on either side. The leather industry continued to be a mainstay of the local economy in the post-medieval period and Market Drayton has maintained urban status to the present-day, though most medieval architecture has been lost to post-medieval redevelopment and fires.