Coggeshall is situated in the valley of the River Blackwater, close to where the river was reached, at a crossing point, by minor routes heading north into the Colne Valley and south to Kelvedon. The Roman Stane Street – an east-west road from St. Albans – ran through Braintree and then through the centre of Coggeshall, just north of the river, before continuing to Colchester. Near to where those two routes crossed are indications of some Roman occupation, throughout the period of Roman presence in Britain, and later Saxon settlement. Domesday suggests a Late Saxon village that was moderately large and served by a church and a mill; the former was probably the focus of the settlement at that time, on the north side of the river, but removed from its bank, up on higher ground for protection from flooding. The manor of Coggeshall was then held by Count Eustace of Boulogne; it is later seen as comprising two parishes – Great Coggeshall north of the river, and Little Coggeshall south of it – though Canterbury Cathedral also held a small manor, made up of a collection of properties within those parishes, in private hands by the thirteenth century. The reduction, between 1066 and 1086, in the amount of forage for pigs suggests that some clearing of forest was taking place at Coggeshall.

It may have been the progress of clearing that made it practicable for King Stephen and his queen Maud, heiress of the Boulogne estates and the prime mover in the project, to found an abbey on the manor, around 1140 or slightly later; this was not on the same side of the river as the settlement, but to the south, although the Blackwater swung south to skirt the east side of the abbey site. The abbey was of the order of Savigny, which was in Mortain, of which Stephen was count, but in 1147 the order joined the industrious Cistercians. Its founders endowed the abbey with the manor of Coggeshall; despite later additions to its property, in Essex and Hertfordshire, Coggeshall remained the principal source of income for the abbey, and so needed to be exploited as far as possible. Construction of the abbey buildings over the decades that followed, along with later expansion and rebuilding into the fifteenth century, must have given some stimulus to the local economy, stone being ferried up the Blackwater and a kiln for making tiles and bricks being established (ca.1160) north of the settlement – this being one of the earliest uses in medieval England of locally manufactured brick, an activity with which the Cistercians were familiar, although tile-making was already an established if small industry in that part of Essex; the kiln would continue in use throughout the Middle Ages and its products would also enable a bridge to be constructed in the thirteenth century, replacing an older timber structure. In addition, like many monasteries, but particularly those of the Cistercian order, Coggeshall Abbey was involved in sheep-farming. Richard I's grant to the abbey of exemption, for itself and its men, from toll at any fair or seaport within the realm, on abbey goods to be sold or those purchased for abbey use, must have been a further stimulant to a local economy based partly on commerce.

M.R. Petchey observed that

"The true organic town, where commercial pressures produced a town with little semblance of planning, is rare in Essex; Great Dunmow and Coggeshall are the principal examples. In both cases, the original village lay away from the Roman Stane Street and migrated towards it to profit from the increase in trade in the early 13th century."
["The archaeology of medieval Essex towns," in Archaeology in Essex to AD 1500, Council for British Archaeology Research Report no.34 (1980) p.113]

This increase in trade was harnessed by the abbey's acquisition of licences first for a fair and then a market at Coggeshall – the only such commercial events the abbey is known to have instituted anywhere on its lands. Although the original grants have not survived, they are recorded in the context of a confirmation in 1325 of grants of various royal privileges to the abbey, and again in a 1389 confirmation. The right to an eight-day fair in August was obtained in 1250, and the charter for a Saturday market in 1256 (a Fine Roll confirming the abbot's payment of 5 marks for the market licence a few months later); this atypical acquisition order – grants of fairs more usually following or being contemporary with those of markets – suggests both a growth in local commerce and that there may have been no market previously existing at the village. The identity of the abbot at that period is uncertain, but it was probably Thomas Quintyn, who is named as abbot in 1256 and is probably the Abbot Thomas mentioned in Feet of Fines from 1251 to 1258, but who had been superseded by 1262; if so, then he may have had the favour of Henry III, who entrusted him with an ambassadorial mission abroad in 1260. It may or may not be significant that this abbot, in 1253, acquired for the abbey a tenement in Colchester, along with the advowson of one of its parish churches; this might have been purely an investment, part of Thomas' wider efforts to expand abbey real estate holdings outside of Coggeshall itself, but having a foothold in such an important market town could have benefited the abbey in other ways. One of Colchester's medieval registers records a list of complaints made in 1317 by a local jury including that several other Essex localities, among them Coggeshall, were holding markets on Monday and Saturday, which were market days at Colchester. Notwithstanding local historian George Beaumont's attempt to use this to explain why the Coggeshall market of his day was held on Thursdays [A History of Coggeshall, in Essex, London: 1890, p.91], there is no reason to think these complaints had any adverse impact on the markets alleged to be damaging to Colchester's; Coggeshall's had, after all, been operating under licence for over sixty years.

That the fair was to be held around the festival of St. Peter ad Vincula ties it to the parish church, which had that dedication – an uncommon one – rather than to the abbey, whose church was dedicated to the Virgin Mary. However, the determinant was probably a chronological one – August being a good time to sell off the surplus wool that been harvested between May and July – rather than institutional or geographical, for Coggeshall's marketplace was not situated close to the church, but on lower ground on the north side of Stane Street, and within easy reach of the riverside. The stretches of Stane Street on either side of the marketplace were known by the Early Modern period as East Street and West Street, thus reflecting the focal role of the marketplace; this thoroughfare appears to be what was referred to as the High Street in 1341, when we hear of the abbot having erected a seld facing onto the marketplace. It must have been the intersection of the two main routes through the manor that influenced this placement of the market, along with the broadened space that was created from the convergence of routes. Whether a secondary settlement had already begun to emerge around this location we do not know, but certainly any settlement around the church was not well-placed to take best advantage of commercial through-traffic. As the market area was vulnerable to flooding and probably marshy for much of the year, any establishment of settlement there must have required reclamation work: draining the marshy water through ditches, and consolidating and raising the drained terrain. The formalization in 1256 of any existing trade activity at this location would have been further incentive for the focus of settlement to shift south-westwards down the street (Church Street) linking the church to the intersection. A deed [E.R.O. D/DU 564/1] datable to the latter half of the thirteenth century records the transfer of a messuage – at later date described as in the Market End of Coggeshall – adjacent to a road leading from Coggeshall's market to the parish church.

All this implies some deliberation and even a measure of planning on the part of the abbey, but whether the acquisition of a market licence was accompanied by laying out plots for a market settlement, or whether any of those plots were held by burgage tenure, is harder to say. The loss of almost all medieval records generated by the abbey – for which we can probably blame the Peasants' Revolt and/or the Dissolution – has deprived us of documentation that might have registered or reflected some town planning initiative. Those surviving deeds that concern tenements facing onto the marketplace suggest them freehold or copyhold rather than burgages, although there are some hints of rents at ancient levels typically associated with burgages; but this evidence is from the later fifteenth century and cannot be taken as representative of thirteenth century tenurial conditions. That in the second half of the fourteenth century the abbey was acquiring tenements within Coggeshall itself might possibly point to an effort to recover properties earlier granted in burgage, in order to re-grant them on more lucrative terms.

Evidence from a manorial survey of 1575, along with property boundaries shown on eighteenth-century maps, hint at the possibility of blocks of properties, of the narrow-and-deep burgage type, laid out along either side of the market end of Church Street. On the northern side of Church Street these tenements backed onto a rear service route once known as Back Lane, though its curving route meant that property depths varied quite a bit; south side properties terminated at East Street. Other blocks of less deep lots can be distinguished along Stoneham Street, running north-westwards from the marketplace, though perhaps no further north than the end of Back Lane. Immediately south-east of the marketplace is another block of the narrow-and-deep properties whose rear terminates at what is variously described as a branch off the river, an earlier course of the Blackwater, or a man-made mill leat; this block was bounded on the west by the street (Bridge Street) running south to the river crossing and on on the east by another block of properties that do not appear to have extended as far as that watercourse. Along the more northerly stretch of Church Street, properties show far less consistency in size. The overall impression is of a settlement that developed in phases, one or more of which might have entailed laying out plots in advance; but this spread of settlement along, primarily, Church Street though also the other streets leading out of the marketplace, quite likely also involved piecemeal and unplanned growth over the course of the later medieval centuries. There is no technical terminology in the surviving post-medieval court records to indicate that Coggeshall, or any part of it, had been accorded borough status by the abbey; but certainly by that period it was being referred to as a town.

Coggeshall's posited urban status and its economic success are attributable more to its growing role as one of Essex's leading cloth-making centres than to its market function. Of the nine named witnesses to deed D/DU 564/1, one was a weaver, another a fuller, and a third probably a draper; we hear of a fulling mill there in 1305, though it was not new then. Indeed, some decline in its market in the Late Middle Ages is indicated by the actions that had to be taken to revive it in 1561. Yet when the cloth trade itself later declined, Coggeshall was able to fall back on its role as a market town dealing mainly in agricultural produce and livestock.

It may be that Coggeshall's fair was intended, at least in part, to furnish the cloth-makers at Colchester and Halstead with wool produced on abbey lands. This local role as a point of collection and distribution of wool would have been a factor in drawing Coggeshall residents into aspects of cloth production and finishing. The industrial and commercial dominance of Colchester (including its magnetism for immigrants of artisanal skill or commercial talent) seems to have inhibited the growth of cloth-making in those rural areas of north-eastern Essex that could be considered Colchester's hinterland; many of the cloth-making centres that emerged – Sudbury, Halstead, Braintree, Coggeshall, Kelvedon, Witham, Maldon – were ranged north-to-south about an equal distance beyond Colchester, less susceptible to its influence, though close enough to take advantage of its market. Yet cloth-making in Colchester itself, as too at Halstead, was an industry faltering in the late thirteenth century, and this left an opening for growth elsewhere. That Coggeshall was already noted for that industry by the close of the thirteenth century is indicated by it being one of a small number of named places whose cloths were exported via Ipswich, while a "Coggeshall cloak" referred to during legal proceedings in the early fourteenth century shows that it was known, as far afield as the Midlands, not simply for the cloth it produced but for at least one specialized article of clothing created from that cloth. Its road connections gave Coggeshall adequate access to Colchester and London markets or merchants, while the River Blackwater would have enabled cloth to be taken to the estuary port at Maldon (although Coggeshall residents' use of Maldon for export is not mentioned in surviving documentation). During the fourteenth cand fifteenth century it maintained its role, although joined by a number of other Essex centres.

The type of Coggeshall cloth referred to in the Ipswich Domesday Book is thought to have been of the chalon (blanket) type; it was able to find a market niche at a time when more traditional products of Colchester and Halstead were being out-competed by Flemish product. But in the sixteenth century Coggeshall's reputation was primarily for a good-quality woollen baize – a variety of worsted – known as Coggeshall White, which referred to the fact it was not dyed; it was colloquially known just as 'coxsall', although the term 'cogwares' was applied in Suffolk to a larger category that included not just whites but also the lighter fabrics of kerseys, and straits. Changes in the strategic emphasis of local manufacture was a gradual process that may have owed something to the influx of Flemings who settled in East Anglia from the reign of Edward III onwards, but also to the proliferation of fulling mills in the region; the same factors help explain the increase in output of the industry in Essex and Suffolk, whereas in Norfolk, with fewer rivers to power mills, the industry stuck with traditional worsteds that were not fulled.

The fifteenth century saw further growth of the role of small towns as cloth-making centres, as craftsmen sought to escape the increasingly restrictive working conditions of the large towns, dominated by mercantile interests. This growth at Coggeshall also owed something to local clothiers who adopted a production system that entailed them supplying the wool, outsourcing the preparation, weaving and finishing processes, then using regional markets to sell the cloth to drapers. One well-known such family was the Paycockes, who can be traced back to a family of Suffolk butchers, a trade that tended to draw wealthier practitioners into owning livestock and acquiring grazing lands, while those who built flocks of sheep were then drawn into the wool trade. In the mid-fifteenth century a branch of the family moved to Coggeshall, where John Paycocke (d.1505) used part of his wealth to build a fine house on West Street, still standing, and his successors expanded that wealth through their cloth-manufacturing enterprise. By the close of the century Coggeshall would be second only to Colchester as the largest producer of cloth in Essex.

The local wealth generated by the industry is evidenced at Coggeshall in Late Medieval and Early Modern fabric surviving within mostly residential buildings – around fifty are known from the fourteenth or fifteenth centuries – as well as the parish church, rebuilt on a grander scale in the early fifteenth century. Several other buildings also reflect Coggeshall's prosperity: a couple of halls that may have served occupational associations – one being a guildhall mentioned in 1463 – of uncertain location but possibly on Back Lane; a two-storey building put up in the late fourteenth century facing the opening stretch of West Street, which served as a market hall on its ground floor and manorial court in the upper storey; and a chapel built in the centre of the marketplace, thanks to a bequest from one of the more prosperous townsmen (1499), though converted into housing for the corn and wool markets in mid-sixteenth century.

Coggeshall could produce men of influence and wealth, derived partly from commerce, in the fourteenth century, as John Sewale illustrates. But at that earlier period fewer Coggeshall residents, other than manorial lords, are conspicuous in the records. One of a previous generation of the Sewale family was a merchant, and even a little earlier than that we hear of a Richard Leschetour as a resident (1321), his name perhaps suggesting a purchasing agent (achatour) for the abbey, just conceivably an ancestor of the fifteenth-century Coggeshall family of the surname Chapman.

The cloth-making industry is also evidenced: as early as around 1225 we have mention of a fuller and a weaver, while by 1286 William le Fulur of Coggeshall had become prosperous enough to be purchasing property there, and the fulling mill of 1305 has already been noted. Others of the same occupation are referenced in 1366 (when selling a tenement to a draper and a carpenter) and in 1389 (when obtaining a quitclaim to a property in Coggeshall – perhaps that in Church Street of which he was recorded as tenant in 1393). A local dyer is glimpsed in 1432, due to his debt to a London grocer, and four years later two immigrant weavers – one from Maastrict – along with a third man of unspecified occupation, who came from Dordrecht, were the Coggeshall residents among a long list of aliens granted denization. In contrast to the wealthy clothiers of the Early Modern period, it is largely the manufacturing end of the industry that is in evidence in the Middle Ages; perhaps this left open at the marketing or customizing end opportunities perceived by some Londoners, for we find a draper and an armourer of that city acquiring property in Coggeshall in 1357 and 1365 respectively; this could have just been investment of profits from their businesses, but their choice of where to invest could also have been based on the availability of a supply of cloth they might use in their work, or buy up to sell in London.

Were it not for the cloth industry, the surviving records would not show much occupational diversity at medieval Coggeshall. Overall the evidence does not paint a clear picture of Coggeshall as an urban entity prior to the close of the Middle Ages, but there is enough to tantalize, and more thorough research may clarify our view in the future.