Maldon was the only place in Essex besides Colchester to be described by Domesday as a borough. As at Colchester the historical core of the town is on an elevated site. It could in fact be described as a hill-top site – something uncommon in relatively flat Essex; though more of an elongated east-west ridge than a mount, the site is prominent in the landscape. It was this character that contributed 'don' to the Saxon place-name, while the first element indicates a cross or some other kind of monument or marker atop the hill, perhaps even a church. This site overlooked, immediately east, the narrowing inland end of a wide estuary, fed by the confluence of the Blackwater and Chelmer rivers, and eventually emptying out into the North Sea; it also would have provided a good overview of the flat and often marshy lands to north-east and south-east. To the west were woodland and heath. Maldon sits on the south bank of the Blackwater, at its lowest bridgeable point. The ridge along whose top the medieval town developed descended steeply to the river, though its southern slope was a more gradual descent. Across the spine of the ridge ran the axial road around which the town developed – incorporating what is now the High Street – along a slightly undulating route; though this route would eventually connect Maldon with Chelmsford, some ten miles to the east, and London beyond, it is not certain when it took on importance.

This was an area likely to attract farmers, who could pasture sheep – the most numerous livestock evidenced in Domesday – and cattle in the grassy marshlands, graze pigs in the woods, take fish and oysters from the tidal waters, and harvest sea-salt along the marshy shores of the estuary (salt remaining a notable local product today). The earliest prehistoric settlers are evidenced on low, damp ground on the north bank of the river, and to a lesser degree the area south of Maldon. The hill-top itself saw some occupation in the Early Iron Age, becoming large enough to warrant a protective palisade enclosure; but this was subsequently abandoned, with some residents apparently moving north of the river to expand the population in the vicinity of what is today known as Heybridge, which rose above the marshy ground between the rivers. When the Romans arrived, they showed interest in the existing modest settlement and converted it to their own habitation, establishing a quayside settlement between the Chelmer and Blackwater, with a through-road from Colchester connecting to a presumed river crossing. Side-roads were laid out and gravel was spread over the damp ground between the roads, for the erection of dwellings and other buildings, though it was never very densely populated, except perhaps at the very core. The principal north-south road through this small town – which included a temple and possibly a marketplace – was at some point extended to Colchester; any market function there was probably primarily for trading agricultural produce from nearby farms and, to lesser extent, the products of local, but small-scale, industrial activity (notably pottery and metalwork); much was for local/regional consumption, though some perhaps for export. Though the port facilities must have helped with importing goods from elsewhere in the Empire, there is insufficient evidence to indicate it played any great role in maritime trade.

This town appears to have been already in decline well before the collapse of imperial authority, the problem perhaps having been partly periodic flooding and the spread of marshy land, due to tidal influx. Early Saxons settled on slightly higher ground just east of the Roman town, though not in such numbers as to suggest an urban settlement. Saxons also established themselves in the wooded area to the south of Maldon, their tribe later giving rise to the name of the hundred of Dengie, which surrounds Maldon on all sides except for that of the estuary.

The earliest documentary reference to Maldon is from 912 when Edward the Elder was in the initial stages of his effort to extend the reconquest of England into East Anglia and create a line of defences to hold off future invasions. Having built burh fortifications at Hertford, Edward moved into Essex, establishing himself and part of his force at Maldon while another part constructed a burh at Witham; in 916 he returned to provide Maldon itself with such fortifications. These facts give further support to the belief that occupation at or around Maldon was continuous through the Saxon period, and they suggest that Maldon may have been a royal estate. The several Domesday entries for different manors at Maldon show the king as the lord of the core urban component, for he had his own manor-house there and pastureland for a good-sized flock of sheep, and was landlord of 180 burgage tenements, along with 18 derelict properties; of this moderately large burgess population, 15 also held some agricultural land, but the remainder had only their houses, so that they must have been traders, artisans, labourers, or providers of other services. Maldon not only had the formal status of a borough but had also been designated a half-hundred, which would have given it a measure of self-government through its own court. Tait believed that the half-hundred had been cut out of Dengie Hundred at the time that borough status was given to Maldon [The Medieval English Borough, Manchester: University Press, 1936, p.49]

Other estates within that half-hundred, or in Little Maldon, which was left within Dengie, had been given, pre- or post-Conquest, to Eustace II of Boulogne, Robert Fitz-Wimarc (by 1086 in the hands of his son Suein of Essex), and Ranulph Peverel; Peverel and Eudo Dapifer had some small interests in the borough itself. While Maldon is not known to have been subject to the kind of revenue-sharing arrangement between king and earl seen in a number of more important boroughs, Domesday does give the impression of something slightly similar at Maldon; for Robert Fitz-Wimarc was sheriff of Essex under Edward the Confessor and William I allowed Suein to succeed his father in that office (not inherently hereditary) for a brief term, while in the years closer to the Domesday survey the borough farm had been assigned to Peter de Valognes – a major landholder in East Anglia, and sheriff of Essex and Hertfordshire for a lengthy term. The burgesses resident on the manor of Robert and Suein shared with the king's burgesses in an obligation, beyond customary monetary dues, to furnish the king with a war-horse and a ship for military campaigns. The Peverel holding corresponded to Little Maldon, which lay in St. Peter's parish. We also hear of the manor of Great Maldon, which seems to have been largely in St. Mary's parish, but may also have included the borough, or at least part of it.

The various Maldon estates, all lying within the later borough boundary, had probably all been a single royal estate at one time until, perhaps around the end of Alfred's reign, parcelled out into separate manors. That retained by the king lay around the ridge-top and across its northern slope, incorporating both the burgages and agricultural land. The burgess community may have been first served by the church of St. Peter – which some feel to have been the elder of the two hill-top parishes (no churches being mentioned in Domesday) – a dedication possibly reflective of commercial activity; the church sat beside the High Street, at the top of what became known as Market Hill, descending northwards from the High Street to the bridge across the Chelmer (Fullbridge). It is more doubtful whether the king's manor stretched as far east as a quayside, known as the Hythe, where there was a small hamlet – a relationship much like Colchester and its Old Hythe. This community had its own church, dedicated to St. Mary, built ca. 1130 on the gentle slope rising westwards towards the hill-top, but evidently replacing something earlier, perhaps of wooden construction, which was given to the collegiate church of St. Martin-le-Grand, London, in 1056 by Ingelric, dean of St. Martin's and an official of Edward the Confessor, along with considerable property, including Ingelric's Maldon holding. Upon Ingelric's death, Edward granted Count Eustace of Boulogne (his one-time brother-in-law) the church of St. Martin and all its property. These facts would associate the Hythe with the Maldon manor within Dengie Hundred held by Eustace in 1086.

Eustace's manor descended to a grand-daughter who took it into her marriage with Stephen de Blois; he, after becoming king, granted it to his brother Theobald, largely an absentee landlord. It was not long, however, before the canons of St. Martin's were complaining that Theobald's bailiff had disseised them of a burgage at Maldon and, through the 1140s, Stephen made successive efforts to instruct his justiciars in Essex – first Geoffrey de Mandeville, then Richard de Lucy – the sheriff, and his own bailiffs of Maldon to investigate the matter, without any evident result. Whether the burgage in question was a ridge-top tenement or part of the Hythe community is not specified. Nor is it clear whether that community included burgesses or was one of men earning their living off the water; a crude plan of the Hythe ca. 1595 shows only a few residences, and most space was given over to port-related functions. Some of the community, however, probably lived along the eastern stretch (Church Street) of the High Street, approaching the Hythe. Archaeology at one site on that stretch revealed some occupation in the Middle Saxon period; though this was partly of an artisanal character, there may also have been fishermen living on the river-bank, close to where they would have beached their boats [Trevor Ennis, Former Croxley Works Site, Church Street, Maldon: Archaeological Evaluation and Excavation, Essex County Council Field Archaeology Unit, Rep. 1763 (2009), p.26].

Edward the Elder's burh was built at the higher, west end of the ridge, re-using at least part of the older, posited Iron Age, fortification; giving a good view of the river, it lay around part of the ridge-top road, and thus protected the route towards London. This was not one of the larger burhs built during the reconquest, but doubtless considered adequate to offer safety to the area's population and contribute to the overall defensive strategy to counter future Viking incursions that might target East Anglia as the entryway into England. The size of any community already established east of that site is unknown, but the meaning of 'Maldon' allows us to at least speculate the presence of a village large enough to have its own church. Furthermore Maldon was important enough to be selected as the target of a Viking counter-attack in 917, though the burh defenders held out long enough for a relieving force to arrive and oblige the besiegers to withdraw. Things did not go so well at the famous Battle of Maldon in 991, when a Viking fleet came up the Blackwater estuary and disembarked; yet, despite defeating the opposing force of the king's ealdorman in Essex, there is no indication the victors went on to plunder the town.

Whether there were residential buildings within the burh enclosure is not known. It may simply have been a refuge for the residents of the region and their livestock. Or perhaps the king's hall was inside and maybe a mint – for coin finds (silver pennies) testify to minting activity at Maldon from the reign of Athelstan (924-39) to that of William II, and Maldon was identified as one of three Essex mints in 925. Despite its early existence, the Maldon mint was only a modest operation – fewer than two hundred specimens of its output have been found; it was, in the Domesday entry for Colchester, grouped with the mint there in regard to the farm paid by the burgesses of both towns for minting rights. Topographical evidence – notably the course of some streets and the name Gate Street preserved for one of them – has been used to argue for the existence of a second, smaller ditch/bank enclosure – built between one side of the burh enclosure and Silver Street. This might have been a more credible alternative location for the royal hall, if we assume it to have predated the burh enclosure; but the hypothesis remains untested, archaeologically. We might also conjecture that the name Silver Street could preserve the memory of the presence of the mint there, in the vicinity of the marketplace – the existence of a mint being additional evidence for existence of a market; a rival market-owner later claimed essentially that Maldon had no market prior to the institution of a mint [see below], but modern historians would not accept such an argument. Though this connection of mint with Silver Street is purely speculative, the presence of like-named streets in some other Saxon towns, such as Warminster and Wilton is associated with marketplace and perhaps mint.

The main focus for civil settlement at Maldon seems to have remained beyond the east gate of the burh, around the High Street from which two streets led down to Fullbridge, a vicinity that also attracted some settlement, and beyond which lay the older and more continuously settled area of Heybridge. The High Street settlement, however, did not continue along the High Street as far as the Hythe.

At the west end of the High Street was a junction (now known, incongruously, as West Square) formed by the convergence between it, the road heading off through the burh and two others entering the site from the west; it is suspected that here may have been the earliest location of the market, contemporary with the creation of the burh and just outside one of its entrances – such being a common location of burh-related markets. Market activity may have gradually extended along, or beside, that westernmost part of the High Street, as far as another junction, from which a street (Silver Street/Cromwell Hill) ran down to Fullbridge. This second junction was flanked by a church dedicated to All Saints, which would have been immediately outside the gateway into the posited second enclosure; the oldest fabric of the church is twelfth century and there is documentary reference to the church in 1189, when Richard I endorsed the endowments of Beeleigh Abbey (founded 1180), which included the churches of All Saints' and St. Peter's; but a Saxon church on the site is quite possible, and the dedication would have been an appropriate one both for a burh-related church (invoking the protection of multiple saints) and for a market visited by travelling traders, whose home communities would have favoured different saints. It was at this point, around All Saints, that market activity seems to have re-focused during the later Middle Ages. Within this space the borough's earliest documented moothall was erected, with the usual design of an enclosed upper floor for meetings of the borough administrators and an open ground floor to accommodate traders; a bell was later installed at one end to supersede the role of All Saints' bell in signalling the time of opening and closing of market sessions. The area around and between the two junctions was one of the residential foci of the medieval town and may have been fully built up by 1292, when a Carmelite friary was founded to the rear of properties lining the south side of the High Street. It is conceivable therefore that All Saints represents the earlier of the two central churches and that it is St. Peter's which – perhaps prior to the time of Domesday – had been built to accommodate population growth further east along the High Street, as well as a spread in the marketplace, rather than the reverse. It is only past St. Peter's that the street's downhill incline becomes noticeable.

It remains possible that St. Peter's might have been the pre-burh focus of settlement; that All Saints parish is surrounded by the parish of St. Peter's has suggested to some historians that the former was carved out of the latter. In that scenario we might be tempted to imagine All Saints originating as a marketside chapel and only later being promoted to parochial status; the restricted size of its churchyard would favour such an hypothesis. Archaeology has shown Late Saxon occupation on the south side of the High Street, opposite St. Peter's, the oldest structural remains dating to the tenth century – the north side of the street, around St. Peter's, not yet having been investigated; structures built in the mid-eleventh century have also been identified on another site along the same stretch of the High Street.

Tait seems to have considered Maldon a planted town of traders and artisans, because it had relatively little by way of surrounding fields, the vast majority of its Domesday burgesses owning no real estate other than their burgage tenements [op. cit., .pp.71, 77, 96]; despite Henry II's charter of liberties, with its highly standardized terminology, not lending any real support to Tait's interpretation – the limits of the borough banlieu being described in terms of natural features, including a field – this urban character of the community appears to have persisted somewhat into later centuries, for of the two dozen Essex towns for which Britnell identified evidence of landless messuages, Maldon had one of the highest numbers (exceeded only by Chelmsford and Barking); though some of these were in Great Maldon, this does not preclude them from having been on the High Street. The large numbers of cattle, pigs, and especially sheep (336, plus 140 in Little Maldon – a reflection of the good grazing available on marshy land) owned in total by the Domesday burgesses are unlikely to have belonged solely to those fifteen said to have held land other than their residential plots; rather, they may have been pastured on common land, such as the Portmansmarsh mentioned in 1403, and the Burgess Mead and Town Downs heard of later. But farming was probably mainly the occupation of residents in areas surrounding Maldon, and the only mill mentioned by Domesday was in Little Maldon. It has been argued that burgage plots were laid out in consistent widths of 4 perches all along the High Street, from burh to Hythe [Maria Medlycott, Maldon - Historic Towns Assessment Report, Essex County Council,1999, p.22; David Stenning and David Andrews, Maldon Conservation Area Review and Management Plan, Maldon District Council, 2006, p.10], but this is principally based on the evidence from three plots at different locations along the street, and on other suspect evidence; it requires far more investigation before we can envisage a planned layout and allocation of plots at any point in time. Certainly the street layout of medieval Maldon gives no clear indication of planning.

On the other hand, the odd parochial configuration might derive from the distinction between the borough proper and banlieu of Maldon. We could entertain an alternative interpretation that the original Anglo-Saxon focus of settlement, – around All Saints, royal manor-house, and marketplace – gradually extended along the through-road leading down to the portside hamlet; this would be a growth pattern consistent with some other small towns. Further, that this development, whether organic or planned, might have been fostered by sheriff Peter de Valognes – intent on extracting more revenue from Maldon – in the neighbourhood east of St. Peter's church. Even that St. Peter's was Valognes' own foundation to attract more settlers to the expanding neighbourhood – an initiative comparable to that at Colchester undertaken by Eudo Dapifer, Valognes' brother-in-law. If so, Valognes' demands on new settlers may have proven extortionate for, he having almost doubled the farm of revenues from the burgesses from the pre-Conquest amount of £13 2s. to £24, the king had found it necessary, by 1086, to reduce it to a perhaps more reasonable £16. Valognes also farmed from the king the borough of Hertford which, like Maldon, came to prominence first as one of Edward the Elder's burhs, had by 1086 a population of similar size and again featuring traders, and had churches dedicated to All Saints, St. Nicholas, and St. Mary – at least two of which existed by 1086.

Nor can we discount the possibility that settlement around the Hythe was similarly extending, in a piecemeal fashion, up the hill in the direction of the market; peculiarities of the boundary between St. Mary's and St. Peter's parish suggest there might have been a spread of settlement in both directions along the High Street. Although much of the eastern stretch of the street, in St. Mary's parish, remained only sparsely occupied throughout the Middle Ages, archaeological evidence suggests that some sites east of St. Peter's were occupied by the tenth or eleventh century [H. Brooks and A. Wightman, Archaeological evaluation and excavation at 143-147 High Street, Maldon, Essex, Colchester Archaeological Trust Report 496 (2010)]. By the late twelfth century there was also some settlement around Fullbridge, likely engaged in industrial occupations such as tanning, dyeing, and fulling, while a riverside lime-kiln, in Portmanmarsh, is mentioned in 1431. The bridge there gave onto a causeway (to keep its route above the marshy ground) connecting to the bridge at Heybridge – that name also emerging around the late twelfth century – although it is not certain when the causeway was built.

Maldon's site was relatively isolated from the rest of Essex, thanks to wetlands to the east and forest to the west; yet its road connection with Colchester was an avenue for trade, and at times Maldon served as a port for Colchester's merchants. Maldon was a natural magnet for maritime commerce, the estuary being deep enough to accommodate large sea-going vessels and provide them with a sheltered anchorage or a choice of beaching-places. Furthermore, its port remained more accessible than the inland quayside at Colchester, which faced problems of silting and of man-made obstacles to navigation. Finds at Maldon of Saxon pottery (Ipswich and Thetford ware) may point to frequentation of its market by regional traders, and perhaps even export of such products through Maldon, while some of the imported pottery of the later Saxon period, found elsewhere in Essex, might well have entered England at Maldon, after the popularity of coastal trading spots declined in favour of urban markets [on this see Alexander Mirrington, Transformations of identity and society in Essex, c.AD 400-1066, PhD thesis, University of Nottingham, 2013, ch.10] The existence of three churches, probably prior to the Conquest, is a reflection of a local prosperity driven by trade, and the likely existence of quayside facilities during the Late Saxon period is supported by the obligation of the burgesses to build a ship for the king upon demand.

In the post-Conquest period, transhipment of goods to and from London must have played an increasingly prominent role in Maldon's commerce; it was probably cheaper for the merchants of landlocked towns close to Maldon, such as Chelmsford and Billericay, to transport bulky wares around the coast to London rather than via the often poor roads of the interior. From the late thirteenth century into the fourteenth we find the occasional Chelmsford man with property interests in Maldon, although some were perhaps acquired through marriage to Maldon widows. Some of the wealthier residents owned sea-going ships, such as William le Palmer, whose vessel is seen engaged in the wine-carrying trade in 1230. That archaeologists have found only modest amounts of imported ceramics, from any period in the Middle Ages, in Maldon itself – most locals apparently making do with locally manufactured pottery – supports the picture of Maldon's port and market as a point of through-put of commercial goods more than a point of local consumption of luxury goods. Although the market doubtless served the farmers of the hinterland, both as sellers and buyers, the few references to fairs at Maldon, until the royal charter of liberties of 1554, likewise suggests the town's commerce was initially limited in scope; the fairs do not seem to have acquired a national reputation, though there is one mention of Colchester cordwainers who attended. The charter indicates that Maldon's fairs then took place around two festivals dedicated to the Virgin Mary – there is a stray reference to that at the Annunciation in a Colchester court record of 1425 – and one to St. Giles; that last also likely predating the Dissolution, which brought an end to the local hospital of St. Giles in Little Maldon. Cases dealing with disputes arising out of the other fairs are recorded as piepowder proceedings in Maldon court rolls of mid-fifteenth century. The oldest extant borough records (from the 1380s) show a pair of fair wardens among the minor officials chosen each year, but a change in their title suggests they were actually market supervisors; from 1438 they were referred to as supervisors of the market and the water, perhaps pointing to the difficulty in confining commercial activity to official locations, although the older and shorter title was reverted to in 1443. We have no specification of their duties, but a complaint by the wardemen in 1417 indicates these included ensuring the market street was washed clean, particularly in front of the moothall, to prevent it becoming dangerous – probably meaning slippery from blood and entrails of slaughtered animals; two years earlier the wardemen had petitioned that butchers be obliged to clean up their own mess, but this would not become a by-law until over a century later. The market wardens do not seem to have played any role in the 'market court' – that is, special sessions of the borough court held by piepowder process – over which the bailiffs presided.

No market is mentioned in Henry II's charter granted ca. 1171 to his burgess tenants of Maldon, and known though a later confirmation by Henry III. This assured to Maldon residents that they: held by burgage tenure; were independent of the judicial administration of the county and the royal forests; were exempt from various ancient impositions or services, including military service outside the borough – except for continuation of the ancient requirement of providing, for forty days at their own expense, a ship when the king had need; and were quit of various tolls at markets and fairs throughout the kingdom, as well as those imposed on commercial goods in transit. While the charter included a phrase referring to this having been the state of affairs in the time of Henry I, it is not clear if this refers to all the privileges or just the obligation of ship service; that obligation had by now extended beyond military needs to whenever the king's entourage made a sea-crossing and, as a letter of Henry II to the townsmen made clear in 1229, was expected to be a vessel properly equipped and furnished with a capable crew. There is no compelling reason to assume that Henry I had issued a charter embodying these grants; such references to the past were often simply recognitions that charters authorized as privileges pre-existing conditions.

Henry II was not over-generous with the liberties he granted his towns, and his charter does little more than recognize Maldon's status as a liber burgus, a half-hundred, a port, and a community of traders. The charter affirmed some importance of Maldon as an urban entity within Essex, which is also seen in that the charter was advocated by the Earl of Essex, William de Mandeville, and witnessed by other leading Essex landlords Richard de Clare, styling himself Earl of Clare, and Roger Bigod the future Earl of Norfolk. William Fitz-Geoffrey de Mandeville's predecessor as head of the family, Geoffrey II de Mandeville, had in 1141 negotiated away from Henry II's mother control of royal interests in Maldon borough; this concession may not have outlived his fall in 1143, for although Geoffrey III was a few years later restored to some of his father's lands, when Henry II confirmed Geoffrey as earl of Essex, he made it clear that lands wrung from the Crown during the civil war were not re-granted. There was no need for Henry's charter to Maldon to mention a market which had long been operational and was a right that could be taken for granted in an ancient borough; the burgesses claimed (1338) that formal market-days were Wednesday and Saturday, although the borough custumal shows that some trading took place on other days of the week, even Sunday.

With this borough charter of liberties the Maldon burgesses had to make do throughout the Middle Ages; yet it was more than most small towns had. Interestingly, it was not registered at London – for purposes of the city authorities having a record of the toll exemption claim – until Edward III's confirmation of 1330, and even then not until twenty-seven years later, when a note of the fact was made on the dorse of Maldon's copy of the charter; charter confirmations by each new monarch were important, for the privileges they conferred might otherwise be deemed expired by external authorities, as Maldon's wardemen complained in 1416, when they urged that a confirmation be obtained from Henry V (a matter accomplished later that year). The privileges granted by charter were supplemented by local customs, some of which gave the burgess members of the community commercial advantages and responsibilities of the sort documented in other boroughs, as well as protectionist measures for the town market.

Part of the reason the burgesses made no further constitutional gains was that the king granted away his lordship of the borough. Maldon was of relatively little consequence to the king as a borough, though it came to acquire – particularly as English foreign policy became more activist in regard to France and Flanders – increasing administrative importance as a coastal port. A half-share of the royal lordship was confirmed in 1284 as belonging to the Bishop of London; the bishop's tenancy of a Maldon manor, held of the king, is recorded in 1259, when it was far from a new situation. The other half-share passed through a confusing series of secular hands, coming by 1315 to the Fitz-Walter family – descended from the Richard Fitz-Gilbert who founded the Clares, and gaining additional lands through marriage to a Valognes heiress – which already held markets in Norfolk at Diss (prescriptive) and Hempnall (licensed 1226), and in Essex at Burnham-on-Crouch (licensed 1253) and Roydon (licensed 1257). Such mesne lords were less inclined to commute, for a fixed farm, the revenues brought them by their seigneurial rights. This change of hands may also explain why the borough would not be instructed to send representatives to parliament before the reign of Edward III. It is almost as if, with Maldon no longer under royal lordship, its status of borough had been suppressed or played down by its new lords. Even after the 1403 agreement between bishop and community, the borough administration did not become much more sophisticated: the wardemen retained more the character of a leet jury than a town council, and most minor officials were still of the kind found in manorial jurisdictions (e.g. bread-weighers, ale-tasters, supervisors of the leather trades, and affeerors of court fines), although the market wardens represent an important differentiation and Maldon's records have a distinctively urban, rather than manorial, character. Alternatively, we might partly blame royal bureaucrats of the thirteenth century, who were often poorly informed or indifferent to the precise status of urban communities; in the hundredal enquiries at the beginning of Edward I's reign, Maldon, though treated separately from any other hundred, was classed under the heading of a villata, while Colchester followed under the heading of burgus; the same classifications are seen in a list of Essex debts owed the king in 1229. But we should not read too much into such instances of imprecision.

The hundredal enquiries of late thirteenth century give no indication Maldon's burgesses were unhappy with their altered circumstances. The only complaint to surface in those proceedings was that the bailiff of Dengie had, in Maldon's marketplace, seized a quarter of oats from two visitors, on the grounds that it was for the use of the king; it is not clear whether the complainants felt the rationale suspect or were just venting the common dislike of the royal right of prise, too often abused. But dissatisfaction found expression a few years later, and in 1287 the townsmen found themselves answerable to the king's court, accused by the bishop and the king (acting as guardian of the heirs of William de la Launde) of setting a fire in the lord's park at Maldon and of resisting the collection of various customary fees claimed by their seigneur, including a toll on bulk sales of salt, and stallage – the last being defined for purposes of the legal proceedings as "that merchants who display their goods for sale upon stalls should pay 4d" [Record Commission. Placitorum in Domo Capitulari Westmonasteriensi Asservatorum Abbreviatio, 1811, vol.1, p.212]. A jury found against the burgesses, except in regard to stallage, they submitting a royal charter in support of that – presumably invoking the exemption from stallage in the 1171 charter. However, shortly afterwards the burgesses' communal seal was put to an agreement with the bishop which acknowledged the above obligations, including stallage. Burgess resentment erupted on future occasions, sometimes involving forceful resistance. In 1403 the bishop conceded various powers of self-administration and sources of revenue to the burgesses in return for an annual farm.

The secular share of the lordship is documented in part by inquisitions post mortem. One in 1302 shows that Hamo le Parker and his wife had had been jointly seised, by feoffment of John de la Launde, of revenues from a moiety of the town, including court profits, stallage, and a toll on ships and boats that landed goods at Maldon. The Fitz-Walter seigneuralty is glimpsed in the post mortems on Robert Fitz-Walter (1328), and his son John (1361) referring to the market toll and court perquisites, and on John's son Walter (1387) in which we also have mention of fairs – these too being held as a moiety, which would suggest that fairs were in existence prior to the partitioning of the king's lordship. It is possible that at least part of the Fitz-Walter jurisdiction in Maldon had been ceded to the burgesses, through a fee farm arrangement, at some point in the 1380s, though there is no direct evidence of this; certainly by 1500 such an arrangement had been put in place by the Darcy lords.

The market remained focused at the junction near All Saints, with some spread, by the close of the Middle Ages, along the adjacent stretch of the High Street (which still retains a bulge attributable to market use), in the form of rows of stalls allocated to butchers and mercers – the former along the middle of the street, anchored at its west end by the moothall, the latter either backing onto the churchyard or along the north side of the High Street facing the butchery. [a clearer picture of the changing market layout and facilities, in the Late Middle Ages and beyond, has recently been given by J.R. Smith, "Maldon’s Old Moot Hall and Market Place: a reinterpretation," Transactions of the Essex Society for Archaeology and History, ser.4, vol.8 (2017) pp.104-13]] Fishmongers are, rather later, seen congregating in the lane running northwards off the marketplace. Butchers were permitted to sell only from the assigned stalls on market days, although could sell from their residential shops on other days. By the sixteenth century, and perhaps earlier, sellers of dairy products were congregating near St. Peter's; in 1416 the wardemen had asked the bailiffs to have public proclamation made, in the four parts of the town (these presumably being the neighbourhoods around the churches and Fullbridge), that anyone selling butter should do so only at official market sessions – likely a measure against hucksters – though this was never issued as a by-law.

Market spread, although not pronounced until the post-medieval period, also involved the growth of shop-based commerce. The now-concealed frames of four fifteenth-century Wealden houses discovered within High Street buildings each incorporated a shop in their end bays, while those of two late fourteenth-century buildings – now the Swan Hotel on the High Street (slightly east of St. Peter's) and the Blue Boar on Silver Street – similarly still include remains of shop-fronts. A shop was part of a property transaction in 1309 and several such transactions registered in the county court involved the transfer of multiple shops during the reign of Edward III, one including a seld. The 1412/13 account of the borough's rent-collector [ERO D/B 3/1/3, f.251v] mentions several selds: one in the second year of a seven-year lease, at 18s. a year; another said to be newly built in the marketplace, rented for 8s.; and three more in the marketplace – two of them, at the east corner of All Saints churchyard, held by a butcher paying 14s. annually. When Essex gentleman Richard Walton died ca.1400 his holdings included in Maldon seven shops and a plot of land on which were seven stalls, property that his sister Joan took to her marriage with Sir Thomas Erpingham. The ballival accounts for 1422 [ERO D/B 3/1/1, f.19r] record two shops under the moothall being rented out, each for 6s.8d annually, one of them to a kinsman of bailiff William Aylewyn, himself a chandler. The accounts for 1446 [ERO D/B 3/1/1, f.33r] show five shops, rented for amounts varying between 3s.4d and 7s. each; by this date market tolls were only generating 2s.8d., royal grants of exemption and the borough's own sale of trading licences having progressively undermined the value of tolls. The right to hold shop was a privilege of burgesses, although other residents came to be allowed it for an annual fee. By mid-sixteenth century the moothall was falling into disrepair; a market house was built neighbouring it to serve corn traders, and later in the century a second market building constructed, beside St. Peter's churchyard, with cubicles for traders offering dairy produce and other foodstuffs sold in small quantities, while borough administration transferred to new accommodations, and the interior of the old moothall would for a time be given over to storage, prior to demolition. By this period market activity was taking place along all of the High Street between the two market houses, an effort in 1562 to restrict the spread of the messy butchers proving untenable.

In addition to the marketplace proper, commerce also took place at the Hythe, where there were warehouses for temporary storage of inbound or outbound cargoes, and a quayside building owned, in the 1360s, by Sir John Bourchier was described as incorporating solar, shops, and cellars. As with the situation at Colchester's port, market activity at the Hythe may have been frowned on initially by the borough authorities, but gradually became accepted. By the fifteenth century quayside stalls were being rented to townsmen. It would be tempting to explain the two market wardens, elected annually as borough officials, as officiating at two market locations: near All Saints and at the Hythe, but the reason for a pair was more likely to ensure at least one would be available for duty at any given point during market hours.

More problematic for the borough authorities was that some cargo vessels attempted to evade either the tolls or the regulations of the borough by landing goods at Heybridge, so that an illicit market had sprung up on the manor of Heybridge, owned by the dean and chapter of St. Paul's, London following a bequest by a mid-tenth century ealdorman of Essex. In 1338 the burgesses complained that this was a violation of their chartered liberties, applicable across a banlieu that (they alleged) incorporated Heybridge; Domesday seems to treat Heybridge, then under the name of Tidwoldington – its subsequent name probably dating from the time when the bridge was built over the Blackwater, around 1200 – as part of the borough territory, though acknowledging the lordship of the canons. The king issued a writ ordering the sheriff to proclaim a prohibition of the sale of commercial goods outside the borough proper [Calendar of Close Rolls 1337-1339, p.448]. But he rescinded that order when the dean counter-claimed that St. Paul's had been granted the manor by Athelstan, long before there existed a market at Maldon, that the manor owned the northern bank of the creek and half the bridge at Heybridge, and that certain tolls had customarily been collected for wares loaded or unloaded on the manorial bank. The burgesses must have pushed back against this reverse, for in 1354 the dean found it advisable to obtain a licence for a Thursday market at Heybridge, as well as for a June fair there, something the burgesses apparently felt unable to challenge on grounds of harmful competition – perhaps their episcopal overlord's influence came into play here – although they subsequently documented, in the borough custumal, their monopolistic claims and asserted the right to impose a toll on commercial traffic crossing Fullbridge. A lighter, carrying sea coal and other goods, was arrested at Heybridge by the borough bailiffs in 1401. A further measure to combat this problem was taken in 1423, when the wardemen ordained that no ship be allowed to pass through the borough liberty without paying a fee, and required the bailiffs not to licence any mariner to pilot ships to Heybridge unless he too paid a fee; in 1448 it was reiterated that the bailiffs should not permit outsiders to transport goods through the liberty to Heybridge – whether by ship along the river or in carts across the bridge – without payment of a fee, nor any burgess without prior licence. Although Heybridge's market thus remained a thorn in its side, Maldon was at least fortunate in having no other market rivals closer than Chelmsford to the west, Witham to the north, and Woodham Ferrers (licensed 1234) to the south; furthermore, its bridges gave Maldon a competitive advantage, in terms of channelling commercial land traffic between Colchester and south-eastern Essex.

Efforts were made, however, to discourage the emergence of rival markets within Maldon's hinterland, both by prohibiting townspeople from selling foodstuffs in that area (i.e. other than in the borough market) and permitting hinterland residents to buy trading licences that freed them from market tolls. At the same time, Maldon men were not above poaching trade from Colchester: a complaint of the latter, mentioned in the context of regulations issued in 1382 to try to control commercial traffic on the Colne, was that boats were being stationed in the Colne to intercept ships and persuade them to take their cargoes to Maldon's port.

Furthermore, in the fifteenth and sixteenth centuries the borough authorities were trying to bring market activities at the Hythe under closer control. Price-setting was attempted: the bailiffs recommended a maximum price to outsider victuallers and, if the latter rejected the recommendation, burgesses were required not to offer anything higher. Burgesses who purchased fish, coal, or other goods at the Hythe were not permitted to retail it on the quayside, but only from their shops within the town, while outsiders who bought goods at the quayside had to have the transactions registered by the town clerk, and were not to re-sell those goods at the marketplace within the town unless they purchased a local trading licence. In 1423 it was ordered that outsiders bringing goods to the Hythe (presumably by water), before displaying their goods for sale there, go to the moothall to declare under oath what they had to sell – information then recorded in an authorized bill of goods – so that burgesses could be kept informed as to what was being offered for sale at the quayside, in order that they might exercise their customary right to a share.

Some prosperity at Maldon during the Late Middle Ages is indicated from private financing of renovation, expansion and beautification of the parish churches, though this mostly seems to have taken place in the early fourteenth and fifteenth centuries. To have a territory encompassing three parishes was uncommon in Essex towns, though population remained focused mainly in the ribbon development along the through-road, from the posited site of the burh to the Hythe; beyond the burh the through-road seems to have received settlement only in the post-medieval period. The crises of the fourteenth century doubtless took a toll on the town's economy, but concerning the impact of plague we have only some tangential indications: in the post mortem on Robert Bourchier (1349), whose extensive Essex holdings included in Maldon borough a mere six cottages, all of them tenantless; and in the wardenship of the leper hospital changing hands several times between 1349 and 1351.

There are other indications that, in the century or so following the Black Death, Maldon experienced some economic contraction, perhaps prompting a reduction in the number of formal market days. Yet some of these are ambiguous, such as the exemption from sending representatives to parliament, obtained in 1388 (renewed 1393 and 1407); for the first followed the drawn-out political proceedings of the Merciless Parliament, which imposed an extraordinarily high cost in parliamentary wages on a borough that had few revenue sources of its own (so that paying those wages sometimes necessitated imposing a special, and probably unpopular, tax on the community), and was struggling to win control of seigneurial jurisdictional rights and associated revenues while at the same time facing repair costs to the deteriorating causeway between Fullbridge and Heybridge. The above-mentioned protectionist proclamation of 1382, evidencing attempts to divert commerce from Colchester to Maldon, may have been a reissue of a document over a century older, and so not indicative of a problem consequent to the bouts of plague. The analysis by Nicholas Amor [The Trade and Industry of Late Medieval Ipswich, PhD thesis, University of East Anglia, 2009, p.92] of data from a customs controller's account indicates that between May 1397 and April 1398 10 arrivals and 18 departures of ships from Maldon's port went on record – considerably fewer than at Ipswich, Harwich, or even Colchester; no wool was among the exports, and the amount of cloth within the cargoes was worth only a quarter of that exported from the other three ports, but butter and cheese were exported in far greater quantity than was the case at the other ports and formed 70‰ of the value of goods exported from Maldon, while imports of wine were relatively modest and only in regard to the volume of iron imports did Maldon outclass Colchester and Harwich. But this source does not cover the coastal business, particularly shipping to London, that was valuable to Maldon, nor does it address goods smuggled out uncustomed, which was only occasionally detected and registered in royal records.

In contrast to evidence suggesting a period of economic hardship, other information points to Maldon striving to weather its difficulties, not least by seeking greater self-determination, free from seigneurial constraints. If recurrent plague had shrunk Maldon's population, its role as a port offered opportunities that encouraged numbers to bounce back. While it is possible the growth in size of merchant vessels during the Late Middle Ages may have gradually limited the number of ships that could reach the Hythe, Wright [The History and Topography of the County of Essex, vol.2, London, 1835, p.638] maintained that in his time ships of two hundred tuns burden could, in favourable tides, reach the quayside. Maldon never became so depopulated that it was reduced to being a village. The poll tax of 1377 listed 542 tax-payers there; although this source is not ideal for estimating population, comparison with the Colchester figure of almost 3,000 at least gives a sense of scale. The populace of the last quarter of the fourteenth century continued to include fullers and dyers, as well as men engaged in selling cloth; the oldest extant record (1384) of an entrance to the borough franchise is of a tailor. But Maldon was not over-dependent on the cloth trade. As already mentioned, local dairy products were a moderately important trade item; in 1357, for example, a Zeeland merchant arrived by sea at Maldon with a cargo of salt, sold it there, and used his proceeds to purchase cheese and butter to take home and sell, while in 1404 Maldon was being considered by a London fishmonger as the export route for a hundred weys of cheese and butter. We also have references, from the 1360s and '70s, to royal licences permitting individuals (one a Writtle resident) to purchase at Maldon large quantities of grain, beans and peas for export overseas or for supplying London's needs, and in 1344 to grain and flour being shipped from Maldon to supply English forces in Flanders and Berwick.

The growing intensity, in the late fourteenth century, of the burgesses' struggle to shake off the chains of seigneurial dominance is another ambiguous element in Maldon's history. On the one hand it might be interpreted as an act of desperation, with economic conditions becoming more difficult and the leading townsmen seeking to bring local revenue sources within their grasp. On the other it could be seen as an expression of self-confidence of a borough elite, or even a clique, building wealth from the growing value of Maldon as a port.

The concessions made in 1403 by the ageing and perhaps world-weary Bishop Robert Braybrooke (he died the following year) were addressed to a named list of burgesses and then to all residents and the community of the town. The first name on the list was that of lawyer Robert Darcy, who was likely either the ringleader or spokesperson of the named group, followed by three men who had been very prominent in the borough administration since the time from which its self-produced records survive: John Welles, John Burgeys, and John Glover.

Between 1384 and his death in 1418 John Welles served nine terms as borough bailiff – perhaps others as the bishop's bailiff – and was twice sent to represent his borough in parliaments. It was perhaps an evident capability or force of character that enabled him to enter the ranks of borough administration very quickly after arriving in Maldon, a newcomer, and he soon took up its cause, being one of those who supported the borough constable in 1386 in an act of rebellion against Walter Fitz-Walter, while the latter was absent abroad, by blockading his servants in one of the town's houses. He is evidenced engaged in mercantile ventures, one being to Zeeland, but may have earned some of his livelihood from administrative roles; in 1388 he was farmer of the mensurage at the Hythe and of the burgesses' common hall in the marketplace, as well as being warden of the bridge at Heybridge (which gave him responsibility for its maintenance).

John Burgeys likewise served nine ballival terms and was eight times the borough's parliamentary representative between 1400 and 1433, being bailiff at the time the 1403 agreement was negotiated. On one occasion Welles was his ballival colleague, the pair having worked together before as farmers of the common marsh (administration of pasturage) in 1402 and perhaps the following few years, Burgeys continuing alone in that role from 1405 to 1408. Both men also acted as collectors of royal taxes, though on separate commissions. Burgeys was explicitly described in both local and national records as a merchant. Some of the pleas of debt to which he was party suggest that fish, shellfish, and cloth were among the goods in which he traded. By 1429 he was being sued for 15 outstanding debts – his creditors including two fishmongers, two drapers, and two ironmongers, all of London, a Writtle man, and the sons of John Glover and John Welles – amounting to £139 6s.8d. in total. Yet he was able to surmount this financial embarrassment and the outlawry that had come with failing to show up in the king's court to answer his complainants. The last context in which he is seen (1436) is alongside Robert Darcy as a witness to a property transaction by which Thomas Welles, a London grocer and probably a son of John Welles, turned over all his Essex properties to a group of other Londoners. We may note that both Darcy and Burgeys evidence some connection with the Bourchier family, though how close an affiliation is difficult to say.

In contrast to Welles and Burgeys, John Glover may represent a longer-established family in the borough; the surname le Glovere is evidenced in Maldon from the very beginning of the fourteenth century, although it is unclear whether all bearers were related. The John Glover who concerns us here served, between 1385 and 1417, nine terms as bailiff (partnering with Welles on four of those occasions) and attended three parliaments on behalf of his borough; in 1388 he was warden of Heybridge. That for decades he rented from the bishop part of a tenement in Fullbridge Street suggests that he did engage in glove-making, an industrial activity that would likely have taken place close to the riverside – one of the bishop's concessions in 1403 was another tenement in that street, of which a Thomas Glover was part-tenant; in 1381 John had sued Laurence Glover of London for having poached his assistant or apprentice. However, there is better evidence for his main source of income being from the cloth trade in general, for he is seen paying aulnage duties on cloth he sold at Maldon in 1394/95 and in that same year sued Colchester dyer John Pod for a debt of £8. He also held a stall at the Hythe, and the 1403 agreement saw him explicitly described as a merchant, perhaps to differentiate him from his like-named son. The son does not seem to have taken over his father's Maldon business, for in 1421 he sold his rights in all his late father's Maldon properties to Robert Darcy, a transaction witnessed by John Burgeys, whose numerous debts in 1429 included £10 to Glover. These three individuals illustrate that, whatever the overall state of Maldon's economy in the early fifteenth century, some of its residents were able to exploit Maldon's commercial assets to build personal prosperity.

The sixteenth century saw further effort at revitalization, through: the acquisition by borough authorities of Admiralty jurisdiction over the rivers, estuary, adjacent coastline, and their landing-places; grant of a royal charter of incorporation (1554, with additions 1555), which played catch-up with three centuries of administrative development in the town, recognizing existing institutions including the Saturday market and three fairs; purchase of a new home for borough administration; reorganization of the marketplace (notably by creating new structures to house dealers in fish, grain, dairy and poultry, along with the hawkers of vegetables, and larger and more permanent structures for the butchery and mercery) – it was now the name Market Hill came to be applied to what was previously St. Peter's Lane; and further industrial development in the Fullbridge neighbourhood. Yet for all that, the medieval street layout and extent of Maldon altered little in the Early Modern period, any population growth being accommodated via sub-division of existing properties and other densification, as well as on land that became available after the Dissolution; little of the few fields or pastures within the borough boundaries, which remained of importance to local victuallers, was given up for building purposes.

Maldon thus continued as a small to medium-size town of a little under a thousand residents, its market mainly of value as a regional distribution point, augmented by its port facilities, a second set of these developing around Fullbridge in the post-medieval period. Unsurprisingly, its port had earlier been well-used for shipping wool abroad, both by Maldon merchants, such as Philip le Draper, (1271) and Benedict de Bradewell (1272), and by outsiders, such as the Colchester ship-masters who in 1339 carried wool on behalf of the Florentine trading companies, the Bardi and Peruzzi, acting for Edward III. When, upon taking the throne, Edward wished to consult with urban experts on economic matters, Colchester and Maldon were the two Essex towns instructed to send a pair of their soundest wool merchants as representatives. Similarly, Edward's reign saw Maldon as a port regularly used for exporting cloth. The town had become known as one of the Essex centres of the cloth industry, its role being perhaps less the manufacture of cloth (i.e. weaving), than cloth finishing and sale of finished products – though possibly the weavers were based in the surrounding rural areas and consequently less visible in borough records. The existence of this industry is not evidenced at Maldon until the second half of the thirteenth century, when we hear of burgesses such as Walter le Draper, the aforementioned Philip le Draper, and Edmund le Tayllur; Philip was sufficiently wealthy to be able to purchase from the king a life exemption from burdens such as tallages, service on juries or in royal posts up to the level of sheriff, and from being distrainable for any debt of which he was not the debtor or the debtor's guarantor. Some Maldon cloths – probably chalons blankets – were exported through Ipswich; the surname Chaloner is found in Maldon in mid-fourteenth century. The open area known as Tenterfield, just south of the High Street and still remembered in a street name, bears witness to that aspect of the cloth industry; in 1413 we hear of six tenter plots rented from the borough by two men (one surnamed Fuller), though their location is not specified.

Maldon seems to have been an exception to the concentration of most of the cloth industry in northern Essex. It lay far enough away from Colchester to be able to develop an independent industry; indeed, it likely benefited from the decline in demand, as the thirteenth century progressed and imported Flemish cloths out-competed burels produced at Colchester and Halstead, by helping develop a chalons product that could sell even in the international market. The needs of the Premonstratensian canons populating the abbey within Little Maldon may have helped stimulate the local industry. There is no evidence of a fulling-mill at Maldon, though the Fitz-Walters had one at their manor of Woodham Walter, just east of Maldon and connected by road to its market; on the other hand, we hear of areas of land set up for tenter operations. Richard Britnell's analysis of cloth subsidy and aulnage accounts suggests that by 1394/95 the markets at Braintree, Coggeshall, and Dedham were doing a better business in cloth – Colchester hanging on to its position as the leading cloth market of the county – and Maldon's market was comparable to that of Chelmsford; by 1467/68 the leaders remained much the same, but Maldon business in cloth had lost ground and even, Britnell felt, "dwindled to insignificance" [Growth and Decline in Colchester, 1300-1525, Cambridge University Press, 1986, pp. 80, 189]. That may be going too far; a list of Maldon men accused in 1401 by the Bishop of London and Walter Fitz-Walter of challenging their seigneurial rights included two (perhaps four) tailors, one or perhaps two dyers, one or perhaps two fullers, and cloth merchant John Floure (whose like-named kinsman, a London draper, was one of the group's mainpernors. Nor should we think that this represented the personnel of the entire local cloth industry, for the inclusion of butchers, shoemakers and a smith suggest the group was selected largely from men familiar with the use of heavy or sharp-bladed instruments suitable for intimidation.

Maldon did not develop any other prominent industrial specialization, though a certain amount of glove-making may have gone on there, to judge from the bearers of the surname le Glovere, and the admission of glover Thomas Estwode to the franchise in 1447; there are also indications of a leather-working sector, though this was common in most towns. We should think of Maldon's economy relying more on its role as a port than as an industrial centre. But it shows a degree of occupational heterogeneity commensurate with a town of its size and its role in the coastal trade, in which coal, salt, timber and agricultural produce seem to have played the largest part. The occupations of new burgess entrants were seldom specified during the late fourteenth and early fifteenth centuries, but we hear of bakers, a skinner, sherman, cordwainer, weaver, fuller, carpenter, smiths, chandlers, mercer, merchant, mariner, and a goldsmith; Maldon participants in Cade's rebellion (1450) included a cook, hackneyman, coverlet-weaver, and tallow-chandler. A goldsmith had been mentioned as a resident as early as 1267, although local needs – even allowing for Beeleigh Abbey – are unlikely to have supported the continuous presence of such elite artisans. Nonetheless, Maldon's importance as an east coast port attracted the interest and influence, though not usually the residence, of some of the major families of the county: the de Veres, the Bourchiers (whose involvement began in the 1320s with Robert de Bousser marrying the heiress of a holder of a moiety of Great Maldon, then in the 1340s acquiring custody of Little Maldon during an heir's minority, Robert's son dying in possession of both manors), and the Darcys (who succeeded the Fitz-Walters as part-lords, and held the Bourchier share while that family was out of favour).