Wellington is situated just north of the Roman extension of Watling Street, which headed down to London, via Towcester and St. Albans; a branch off it connected to Shifnal. To the north of Wellington a medieval route known as the Portway connected Newport and Shrewsbury. A road running south off Watling Street led to Worcester. None of these ran through the village itself, which was served instead by roads with more local connections. The main route into Wellington was via the present Park Street/Church Street, from the north. South-west of Wellington rises the Wrekin, a prominent hill topped by an Iron Age fort.
A manor whose church, evidenced in Domesday, was probably the focal point of the village, Wellington was in 1210 granted at farm to Thomas de Erdington (d.1218), who was sheriff of Shropshire and Staffordshire 1205-14; by 1212 he held it on a more secure basis, by knight's service. As one high in King John's favour, he had some years before received the Shropshire manor of Shawbury by royal gift. A licence for a Thursday market and June fair of three days at Wellington was issued in 1244 to his son Giles, who had succeeded Thomas after emerging from his minority around 1221, though he had to sue another claimant and the case was not settled much before 1229, while in the years that followed he was preoccupied with a lawsuit to recover Shawbury from a lessee, not resolved until 1239. He seems to be the same Giles de Erdington who, described as Dean of Wolverhampton, acquired a market licence in 1258 for the town of Wolverhampton (Staffs.) and in 1263 granted the burgesses a charter of liberties modelled on those of Stafford; the town may have existed for some decades, however, for in 1204 King John took exception to an unlicensed market (first heard of 1179) being held there. Giles was evidently in holy orders (he not having been his father's original heir, but a younger son), for he served as a royal clerk, much employed as a justice of assize from 1245. He was unmarried and succeeded (1268) in his estates by a nephew who died in 1282 leaving an underage son.
The population of the Domesday village was small, but must have grown quite a bit to generate enough commerce to warrant the pursuit of a market licence. The market may originally have taken place in or beside the churchyard; early routes within Wellington seem to have been aligned on the church. A green immediately north of the churchyard, taking the form of a funnel-shaped widening of that part of Church Street, has been interpreted as a more likely site for the village market, perhaps in existence prior to the Conquest, but almost certainly afterwards For those not heading for market or church, a fork off Church Street, known as Back Lane, bypassed the centre of Wellington and took travellers through to Watling Street.
The 1244 licence was doubtless preceded or followed by the establishment of what looks like a planned town south of the churchyard, and it was probably in this context given growing official disapproval of marketing in churchyards that a new, rectangular marketplace was established, which is certainly where the market was held in later times. Church Street was extended south, around the churchyard, to connect to this marketplace, and the new stretch of Church Street seems also have been used for market activity, for it was included under the name Market Place up to the early nineteenth century. The town was probably laid out around this part of the street and the new marketplace (the current Market Square, now much shrunken consequent to encroachment), with the green perhaps continuing in use for the fairs and/or as a livestock market. What was known as New Street suggesting it a slightly later expansion of settlement, albeit along what might have been an existing lane ran off the north-east corner of the marketplace and swung south-eastwards (as what is the present High Street, the product of build-up in the eighteenth century) to a junction with Back Lane, and thereby to Watling Street. From the south-west corner of the marketplace the later-named Walkers Street headed west to connect to the Shrewsbury road. Off the street connecting the new and old marketplaces ran westwards what became known as Butchers Lane and later Market Street. Further south, Newhall Street ran parallel to Walkers Street; it may represent part of the original layout or a later extension of settlement. In addition to fronting the market street and marketplace, burgage plots are discenible along Walkers Street, the opening stretch of New Street, and to east and west of The Green. We cannot be certain if these were all components of an initial plan or represent piecemeal development over the course of decades; New Street, for instance, may have come into existence soon after 1300 as a planned extension of the town.
It was in the context of the laying out of New Street that we first have documentation of burgages (1301) and burgesses were mentioned in 1346. The right to trade was restricted to burgesses, a status initially limited to burgage-holders, although others could buy annual trading licences (giving the status of tensers), and by 1346 tenser status could be purchased for life. No charter of liberties was ever issued to Wellington, but community concerns and desires were expressed, through the manorial court, by a jury of residents, whose membership changed from year to year, although leading townsmen predominated; bailiffs an office in existence by 1315 were chosen by, and perhaps from, the jury.
By 1283 lordship of Wellington had been acquired by Hugh Burnell, and would remain with that family which already had a history of developing market towns through the rest of the Middle Ages. Hugh's renewal in June 1283 of the market and fair grants, which he supplemented with an August fair, was a necessary step since he was not an Erdington heir, and so does not point to any need to reinvigorate local commerce. Hugh had also, the previous month, obtained licence for a market and fair at his manor of Rushbury, also in Shropshire. His son Philip furnished the borough of Malpas (Ches.) with a market licence in 1281, and it was perhaps he who established a new town on that manor, for burgages are first heard of there in the 1280s.
The growth of Wellington's commerce, at least prior to the Black Death, is likely to have been steady, if unremarkable. As was typically the case with small market towns, the primary purpose of market and fair was to facilitate and stimulate redistribution of surplus produce and stock from the surrounding rural lands, some of it repurposed by local craftsmen into secondary products; but, as usual, it was the wool trade and ancillary cloth industry that increasingly made up a large share of business. Cloth finishing and manufacture of cloth products is evidenced in the town in the fourteenth century, through surnames: Chaloner, Mercer. Shearman, Tailor, Teyntour (dyer), and Walker. Other surnames point to leather-workers, although (in the absence of a sizable local watercourse) tanning may not have played a large part in the local economy, and by the fifteenth century tanners from Shrewsbury were selling hides in Wellington's market. Walker Street also points to the presence of fullers in the town, while an alley named Ten Tree Croft, running from the marketplace out to an open area, recalls the presence of tenters on which fulled cloths were dried in a manner that avoided shrinkage. In 1514 Wellington was granted to Christopher Garneys, the prize for beating Henry VIII in a game of cards; Sir Christopher was prompt in renewing the licence for the existing market and original fair, but substituted a November fair in place of the August one.
Wellington has left us little medieval documentation, there has been no significant archaeology undertaken, and it has relatively little by way of architectural heritage. As far as we can tell, its population grew but slowly over the Late Middle Ages, while those of the various neighbouring hamlets seem to have shrunk. The 1327 lay subsidy suggests that Wellington was comparable in size to Market Drayton, Newport, or Much Wenlock; its growth rate over the next century was also similar to those other towns. In size and wealth it could not rival that of the leading towns of the county until the eighteenth century, when a period of rapid growth led it to become the second most important town in the county. Yet just to survive in Shropshire as a small market town through the Late Middle Ages, weathering the competition from the markets of Shrewsbury and Newport, while besting potential challengers the new-comer markets of Madeley and High Ercall was an achievement.