Harwich attained, and has retained, its importance as a North Sea port. Situated at the north-easternmost point of the Essex coast, it stands at the narrow end of a promontory jutting out into an estuary formed by the combination of the Orwell and Stour rivers; this wide estuary is thought not to have acquired its present extent until around the beginning of the twelfth century, as the rivers shifted course from more ancient points of entry into the sea. The resulting product was a natural harbour, wide but fairly well sheltered, being protected somewhat by a second promontory to the east. The value of its harbour meant that Harwich was, particularly in the fourteenth century, the assembly point for medieval English fleets or embarkment point for expeditions to the continent and supplies for forces already active there (though these supplies were mostly acquired elsewhere in Essex), and becoming useful as a shipbuilding centre by the close of the Middle Ages. But it also made it the location of sea-battles (in the case of resistance to Viking raiders), invasion (in the case of Queen Isabella, returning from Hainault to overthrow Edward II), and assault (in the case of a French raiding fleet in 1339), the last prompting the initiation of construction of defences there. Proximity to the sea assured Harwich an enduring success as a port that eluded Colchester and Maldon, located more inland and plagued by problems of increasingly difficult navigation to reach open sea; on the other hand, Harwich's isolated position meant that it lacked much hinterland of its own, and so its economy relied on its shipping services and its development as a market centre for catering to maritime trade; this role put it in competition with Ipswich, further up the tidal Orwell, a rivalry that could become hostile.

Harwich arose within Dovercourt parish, though it would out-develop Dovercourt village, situated a little further inland on the Tendring peninsula. Roman and earlier settlement is evidenced on the site of Dovercourt manor, and it is likely there was a minor Roman road leading there from inland Essex. There is also archaeological evidence of a Saxon cemetery. Dovercourt was mentioned in Domesday, unlike Harwich, which is generally assumed to have been an outlier of the manor. By 1086 Dovercourt was one of the estates of the de Vere family – there perhaps being an etymological connection between the place-name and family name – and thereby became part of the dowry Juliana de Vere took to her marriage to Hugh Bigod, the first Earl of Norfolk; despite the dissolution of their marriage, the earls remained sub-tenants of Dovercourt, holding of the de Veres. Hugh's son by Juliana, Earl Roger Bigod, founded a chapel at Harwich, but after Hugh's death Dovercourt's church and Harwich's chapel were given to Earls Colne Priory, a de Vere foundation, to support a chantry for the Bigod family. This event marks the first occurrence of the name Herewyche and the gift is sometimes dated to ca.1177, the date of Hugh's death, but Roger did not come into his estates until 1189, as his stepmother was claiming them for her children by Hugh; furthermore, one of the witnesses to the deed [Dugdale et al., Monasticon Anglicanum, rev. ed., vol.4 (1823), p.102] was Roger's son, who was not born until about 1182, and the deed also mentions Roger's wife Ida, whom he did not marry until 1181. Despite the presence of the chapel, the site of Harwich does not appear to have attracted much permanent settlement, other than of fishermen; this was perhaps due to the lack of a freshwater source and the high saline water-table (making wells useless) – many medieval properties subsequently had underground cisterns in their backyards to collect rain-water.

The harbourage received documentary mentions in the context of Saxon/Viking conflict in the ninth and tenth centuries, and the name Harwich, of Saxon derivation though not recorded until later, may point to use of the site as a military camp, an interpretation meagrely supported by a single find of a Viking ring and Morant's observation of an earthwork, since lost to coastal erosion. On the other hand, the suffix 'wich' suggests that Harwich might have been the location of sporadic and informal trading encounters between Scandinavians and Anglo-Saxons; the position of the site encourages such an hypothesis. A recent study has argued that cumulative archaeological evidence from the entire area around Dovercourt favours the idea that foreign goods were being imported there from at least the sixth century – perhaps exchanged for pottery produced elsewhere in East Anglia or for supplies to sustain an army camp – even though that evidence is not yet strong enough to make it clear that Harwich was the landing place for such goods [Alexander Mirrington, Transformations of identity and society in Essex, c.AD 400-1066. PhD thesis, University of Nottingham, 2013, pp.143, 176, 225, 263, 329]. At Colchester too, small finds of imported items are found from the greater part of the Anglo-Saxon period; while these could have come to Colchester up the Colne, it is not inconceivable that Harwich might have served as a landing-place not only for its region of Essex but even for Colchester in at least the early Saxon period.

However, any such role seems somewhat disconnected from urban development at Harwich, which belongs to a later period. For it was in the early thirteenth century that the earls of Norfolk pursued an economic development venture there to compete with Ipswich; the deep water of Harwich Harbour meant that it could receive ships and provide anchorage during all tidal conditions, giving it an advantage over Ipswich. This venture entailed establishing a planned market town. Harwich received official acknowledgement as one of Essex's ports when Henry III informed its residents, in 1229, of the appointment of a new custodian of Colchester castle, and it was contributory to a royal subsidy in 1238; but neither of these unequivocally evidences urban status. In the context of invasion fears in 1264, the coastal towns of Norfolk and Suffolk were ordered to assemble defensive forces, but Essex residents were ordered to prepare to defend the port of Harwich – it appears the royal bureaucracy was conscious of Harwich's role as a port but less clear on whether it had urban status. As late as 1340 the Ipswich authorities could portray Harwich as merely a hamlet within Dovercourt, itself not even a royal manor; but this belittling was to serve their legal battle to prevent Harwich from usurping Ipswich's jurisdiction in the Orwell.

Harwich had become more than a hamlet. In 1253 another Roger Bigod, 4th Earl of Norfolk, had acquired for it a licence for a Tuesday market and an Easter fair of unusually long duration (10 days); his inquisition post mortem (1270) considered Harwich important enough to explicitly mention it as a member of Dovercourt manor. Since Roger owned a house with quay in Ipswich, we may wonder whether the notion of competing with Ipswich's market had a personal dimension in regard to his personal imports/exports. It seems likely that Harwich's layout was re-planned in conjunction with this market licence. That this licence only formalized an existing market is suggested by a complaint, made before the king's justices at Chelmsford in 1254, that the men of Harwich were prone to committing commercial fraud, by using one measure when buying and another when selling. [Samuel Dale and Silas Taylor, History and Antiquities of Harwich and Dovercourt, London, 1730, p.135].

The next earl (Roger IV) was prepared to take matters even further beyond the bounds of the law to advantage Harwich's commerce, authorizing the officials of his manors on either bank of the Stour/Orwell estuary – that is, Dovercourt and Walton – to prevent any ships that anchored there from proceeding upriver to Ipswich, but instead oblige them to sell their cargoes at Harwich; Ipswich naturally complained to the king. A like indication of Roger's tactics is seen in the case of Dunwich, which complained that the earl had instituted a blockade of its port, by land and sea, for six days and had imprisoned some of its burgesses at his manor of Kelsale (see below) a few miles inland. Roger's strategy at Harwich may have been assisted by the inclination of some wine-importing merchants to evade the king's wine prise by landing their cargoes at Harwich, though the ploy was discovered and in 1275 the king ordered his buyers to apply the prise at Harwich too. In the following century Harwich felt confident enough of its position to mount a legal challenge to Ipswich's claim to jurisdiction over the stretch of the Orwell connecting it to the sea, which included the power to collect tolls at Harwich harbour. Although this challenge ultimately failed, the Ipswich authorities had to remain constantly watchful to protect their control of the Orwell and, in the reign of Henry VI, required owners of commercial vessels to help furnish a fleet of patrol boats to keep an eye of the efforts of Harwich men to divert cargo ships to their own port

The Bigod, or Bigot, family came to hold a number of market centres. It established itself in England through a Roger, member of a somewhat obscure but knightly Norman family already in service to Duke William; it assisted in the Conquest and was rewarded with estates across East Anglia -- mostly in Norfolk and Suffolk, but a few in Essex (north-west of Colchester, none near Harwich). Having assisted Ralph de Guader, Earl of East Anglia, to repulse a Danish invasion attempt, Roger was, after Ralph's fall in 1074, made sheriff of Norfolk and Suffolk and received many of Ralph's estates, to which he subsequently added others. One of his Suffolk manors, Kelsale, had by 1086 a market, said to have been by grant of William I. The caput of Roger's Norfolk estates was, however, at Thetford, where he founded a priory and may have built the castle (although Guader might have been responsible for that). A sizable Domesday borough, location of a mint, and (up to 1095) seat of a bishopric, Thetford must have had an important market prior to the Conquest, its traders serving not only a large region of Norfolk but also other parts of England, and it was the centre of an industry producing pottery that was exported across the North Sea; however, the town underwent a marked decline in the twelfth century – probably due to the commercial growth of Lynn, Norwich, and Bury St. Edmunds, and to loss of its dominance in pottery manufacture – before reviving as a more modest market town. In Suffolk the Bigod base was at Framlingham, whose castle is more confidently attributable to Roger, since Henry I had in 1101 approved its construction.

After Roger I's eldest son and successor, William, drowned in the White Ship disaster, William's brother Hugh succeeded to the family estates; during the civil war Matilda bribed him to withdraw from support of Stephen by conferring on him the earldom of Norfolk, and Hugh managed to hold onto this, despite continued rebellious tendencies. His son Roger II (ca.1144-1221) succeeded to the earldom in 1189. In 1200 Roger II was granted a market for his Suffolk manor of Walton, where a fair (mentioned 1307) may already have been in existence, since we have no record of a grant of it. Three years later, Roger obtained a licence for a fair at Hanworth (Norf.); in this case we may suspect that a market (mentioned 1274) was already in existence. Roger II also rebuilt the family castle at Framlingham (destroyed by Henry II after Hugh I's rebellion), on a larger scale, which entailed some re-planning of the settlement just outside its walls and already protected by its own ditch/bank defences. Framlingham has something of the look of a Norman town stretching between castle and church, although it may have had some importance as an estate centre in the Anglo-Saxon period [Magnus Alexander, Framlingham Castle, Suffolk: The Landscape Context, English Heritage Research Department Report Series, no.106 (2007) pp.6-8]. Its market, perhaps dating from the time of the original castle, is heard of in 1270 and apparently required no license; neither did its two fairs, the oldest a Michaelmas event (the parish church being dedicated to St. Michael). Yet in 1286/87, under the last Bigod earl, the market – now held on three days a week (suggesting it a flourishing and important institution in the region) and on a site that shows indications of being one outcome of the re-planning – was being farmed out; by that time, but perhaps only just, Framlingham had acquired borough status and in the next century we find it granting foreign burgess status to outsiders who were regular users of the market [Paul Bradley, Framlingham Conservation Area Appraisal: Supplementary Planning Document, Suffolk Coastal District Council, 2013, p.6; Alexander, op. cit., pp.35, 42].

Roger's son, Hugh II Bigod, succeeded to the earldom in 1221 but lived for only four more years. During that time he obtained a provisional market licence for Dovercourt (1222), for a Thursday event. There is no indication his successor sought confirmation of the licence after Henry III came of age (1227), and we hear no more of a market at Dovercourt. Perhaps Hugh's successor had, by the time he came into his own, already decided to develop Harwich instead. The village of Dovercourt would have been a perfectly acceptable location for a market, from the perspective of placement on a through-road connecting coast and Colchester; but in the context of developing Harwich as a port, a market closer to where cargo ships moored made more sense, attracting potential transactions even from ships just passing through, whereas Dovercourt was a mile distant and would not attract such casual traffic. On the other hand, if Harwich were indeed a member of Dovercourt, it is quite conceivable the 1222 market was itself intended for Harwich and that the only reason for the 1253 licence was the addition of the fair. Hugh II had been closely associated with his father in the latter's participation in the baronial opposition to King John, and in management of the family estates. Thus, in 1199, he paid the king 40 marks for a two-day extension to an existing fair at Bungay (Suff.), which was for a while an important family residence.

Situated by a crossing of the River Waveney and with harbour facilities on the river, Bungay had been a Saxon burh, partly protected by the bending river; by the time of the Conquest it was quite a large settlement, with a mint operated by Jews, its population served by five churches, three of which were within the burh area. After acquiring lordship of Bungay in 1103, Hugh I Bigod added (1165) a stone keep to an existing Norman castle, which re-used part of the burh fortifications, and he may have extended the earthworks too. Roger II obtained jurisdiction of that stretch of the river between Bungay and Beccles, with its fisheries, a source of modest income. The castle, wrecked after an assault in 1174, was largely and more sturdily rebuilt by Roger IV, the 5th earl, in the 1290s, though let fall into ruin after the close of the Bigod era. The street-plan of Bungay looks as though it was an adaptation of the layout of burh streets to accommodate the imposition of the castle earthworks, though whether due to the Bigods or their predecessor as tenant, William de Noyers, is not clear. Since the marketplace, at the southern end of Broad Street, was located immediately outside the castle – at the junction of roads to Ipswich, Norwich and other parts of Norfolk, and with direct access to the river crossing – Noyers or Hugh I may have redeveloped Bungay as a castle-town, as suspected Suckling [The History and Antiquities of the County of Suffolk, London, 1846, vol.1, p.120], the settlement being contained within a ditch extending from the castle fortifications; that ditch was backfilled in the late thirteenth or fourteenth century. In 1228 Bungay was treated as a borough for eyre purposes. That same year we have a mention of its market as a possession of Roger III (who had only just succeeded to his estates), though farmed out – likely to the burgesses – for the respectable sum of £15 6s.8d. However, several decades later the inquisition post mortem on Roger valued the market only at £6 13s.4d, though two fairs were said to bring in another £4 13s.4d; this seeming decline in profitability may have been due to growing competition from other markets, such as that at Loddon (see below). One of the fairs took place in May around the festival of the Invention of the Holy Cross and the other in September to coincide with the Exaltation of the Holy Cross, a Benedictine nunnery founded within Bungay in 1160 being dedicated to the Holy Cross.

Hugh II's son Roger III Bigod (1209-70), the 4th earl, succeeded to the earldom while underage; he briefly became the ward of William Longespée, Earl of Salisbury, whose family has elsewhere been noted as very active in founding markets. Though Roger (or rather his guardians) obtained management of Hugh II's estates in 1225, he did not personally acquire full control of the earldom until 1233, so it seems doubtful that any further action to develop Harwich would have taken place before the late 1230s. It might be thought that Roger III had more time than his father to be active in developing the commercial potential of his estates, despite part of his career being taken up by his support of the Montfortian party in the war against Henry III. Yet, apart from his initiative at Harwich, the only licence Roger or his guardians obtained (1228) was for a short June fair at the manor of Harleston (Norf.), which evidently already had a market, since such was mentioned in his inquisition post mortem; in 1260 he obtained a second licence for a longer fair in August, probably additional to rather than replacing the original event. By 1369 the settlement of Harleston Market had become a distinctive unit within the manor. Harleston manor was situated where the London to Yarmouth road (via Bungay) crossed the Waveney and may have developed as a market settlement adjunct to Redenhall, which lay across the county border in Suffolk and contained the parish church. Harleston had only a chapel at the apex of the marketplace, a triangular area around which Harleston developed and along one side of which ran the through-road (now The Thoroughfare), while the other side (following later infilling) is now flanked by Old Market Place and Broad Street.

Roger also had a financial interest in the market (licensed 1269, but in existence by 1254) at Loddon – a village on the Norwich-Beccles road and just a few miles off the London-Yarmouth road – though he was no tenant there. Loddon also developed around the nucleus of a marketplace, the highest point on the site, with the church to one side of it, and flanked by the through-road, which led to a ford across the river before continuing to Norwich. Although Roger's post mortem associates his interest in Loddon market with his tenure of Ditchingham manor (part of the first earl's estates), about five miles south of Loddon but adjacent to and now essentially a suburb of Bungay, the financial interest – an annual payment of 20s. – was the result of a settlement between Roger and the owner of Loddon's market, whereby Roger agreed to drop his court challenge to the Loddon licence on grounds of detrimental competition to Bungay. Roger III also had lordship of Great Chesterford (Essex), whose market is mentioned in 1254 when Richard, Earl of Cornwall (husband of Roger's aunt) complained it was damaging his own market at Newport – which suggests that Roger may have been instrumental in fostering a market at Chesterford; perhaps the challenge was successful, for no market is mentioned in the post mortems on Roger III or Roger IV. This was a manor that had come to Roger III from his mother, a daughter of the powerful William Marshal, Earl of Pembroke, from whom Roger also inherited the office of Marshal of England. Part of the manor of Hollesley (Suff.) may have come to Roger from the same source, though part was a long-time possession of the Bigods; Roger's post mortem mentions, as an appurtenance of this manor, an unlicensed market at Margritestowe, but this looks like an error, for the post mortem on Roger IV mentioned only the better-known fair held on the festival of St. Margaret.

Hugh II's younger son, another Hugh Bigod (1211-66) also became involved in market development, consequent to his marriage to heiress Joan de Stuteville. In 1254 Hugh and Joan acquired market licences for two of her Yorkshire manors, one at Hessle, situated on the River Humber (though well inland), and the other at Kirkby Moorside, which Joan held only as dower from a previous husband. In 1258 Hugh was appointed Chief Justiciar of England by the baronial council, of which Roger III was a member, put in place by the ascendant Montfortian party; however, he resigned two years later and subsequently went over to the royalist cause. This assured the family its continued prominence for another generation, since Roger III died childless and was succeeded by his nephew, Roger IV (1245-1306), son of Hugh. The inquisitions post mortem (1307) on Roger IV Bigod were undertaken with greater effort – those on Roger III being consulted and new inquisitions held – and more voluminous result than that on Roger III; this was in part because Roger IV had expanded the Bigod holdings, but also because he died without any children, and his nearest relative, his brother John, was a cleric, so that the earldom and much of its estates escheated to the king, thanks in part to the latter's political manoeuvring to benefit his own family.

Roger IV de Bigod's involvement in commercial development of his estates was, in relation to the number of estates he held, about as measured as that of his predecessors. In 1282 he is seen in possession of a market at Acle (Norf.); though it has been claimed [several Internet sources] that a market licence was obtained in 1253, this licence actually pertains to an Acle in Essex (Great Oakley), owned by Richard de Munfichet – the confusion seems to have arisen from the fact that markets at both Acles were held on Thursdays. The Norfolk Acle's market may have existed from pre-licensing times, for the church there has a Saxon dedication and still preserves its Saxon round tower, and Acle was an estuary port in Roman Britain; Acle is another of those villages by a river-crossing on a route between Norwich and Yarmouth, of which the Bigods held several, and seems to have been one of the Guader estates that eventually came the way of the Bigods [R.H. Mason, The History of Norfolk, London, 1885, pt.5, p.12]; residences clustered around a likely marketplace at the junction of several roads (probably originally a crossroads), one of which passed between the church and manor-house. One of the Bigod earls, probably Hugh II, founded a small Augustinian priory beside the river-crossing; he also obtained from Henry III a grant of toll exemption for his Acle tenants, perhaps only a confirmation of an earlier concession by Henry II. Acle lay a few miles north of Halvergate, another manor acquired with the earldom, and could be referred to as Acle-iuxta-Halvergate. In 1303 Roger IV licensed a market and fair at Halvergate. This, even though Halvergate was a little off the Norwich-Yarmouth road, was perhaps a response to the growing commercial importance of Yarmouth – where Roger IV held a few properties, though one was in disrepair and another not built on – and to the growth of the wool trade, Halvergate Marshes (on the same estuary as Acle) being a major sheep-grazing area as early as the time of Domesday. We may note that Halvergate's fair was not timed to coordinate with the June festival of the saints to whom the parish church was dedicated, but with a festival in late August, closer to the end of sheep-shearing season. It was, however, precisely the increasing dominance of Norwich and Yarmouth over the region's trade that caused such lesser markets – particularly those that, like Halvergate, were somewhat isolated – to decline after the Black Death adversely impacted rural productivity.

Roger IV had also, on 29 July 1302, acquired licences for a market and fair at each of Earl Soham (Suff.) and Watlington (Oxon.). A few miles west of Framlingham, Earl Soham was situated on an east-west Roman road that ran through central Suffolk. It probably came to Roger through his first wife Aline, daughter and heiress of Philip Basset (d.1271) of Soham (Cambs.), whose father Alan Basset had granted market town High Wycombe (Bucks.) to its burgesses to hold at fee-farm (1226). The date of Earl Soham's fair, in early September around the Nativity of the Virgin Mary – to whom the parish church, possibly only built ca.1300, was dedicated – may point again to wool as one of the local crops, though Domesday records only a small flock of sheep present. An alternative partial motivation for establishing a market at Earl Soham was that the later Bigod earls had a hunting lodge and deer park there, on the opposite side of the through-road from the church. As at Acle and Halvergate, settlement at Earl Soham focused on a single street, and none of those villages developed more occupational diversity than would be expected in what were primarily farming communities.

Watlington already had a market, which Richard, Earl of Cornwall, had furnished with a licence in 1252; Richard held it from 1231 as part of the Honour of Wallingford, of which Watlington was an administrative centre, but it had changed hands several times prior to his lordship. After the death of Richard's son and heir (1300), Watlington was one of several estates granted by Edward I to Roger Bigod, who took advantage of the need to purchase a new licence to alter the market day and add the fair. There is some indication of the introduction of a planned street layout in an area of Watlington away from the original village nucleus around the church, and this may represent an attempt to found a new town, but when that occurred is unknown, and there is no evidence that residents acquired the liberties of burgesses. Nonetheless, Watlington is generally considered to have been a market town by the close of the Middle Ages, though never a very prosperous one: its market, probably trading mostly wool and grain, was unable to compete in the long-term with those of Henley and High Wycombe, and lacked any prominent industry to bolster commerce.

The Pembroke inheritance had brought to Roger IV a share of the Marcher lordship of Striguil (once of the Clare family), after other children of William Marshal had perished without heirs; Roger IV's post mortem shows the lordship's properties in Gloucestershire and Monmouthshire, along with even more extensive lands in Ireland, presumably also from the Marshal inheritance, although Roger spent no time there. A Marcher lordship would explain why Roger was able, in 1294, himself to grant, to his feoffee and lieutenant John ap Adam de Sebury, a licence for a Wednesday market and three-day fair around the festival of St. Margaret in the manor of Beachley (Gloucs). Situated on a bank of the Severn, at its main crossing-point (by ferry), on the route between southern England and southern Wales, Beachley was essentially a suburb of the borough of Chepstow (Monmouth.), a planned Norman castle-town and port at a strategic crossing-point of the Wye. The Beachley licence seems to have been intended for implementation in the borough, which was also under Roger's lordship. Roger had already expanded the castle, built a defensive wall around the port (the main Welsh base for import/export), and installed in that wall a toll-gate to control access into the town and ensure outsiders paid tolls before bringing their wares to its marketplace; the market doubtless pre-dated Roger's time and the fair may also have come into existence before Roger confirmed it through his licence. Though originally known as Striguil, the town had by the time of Roger's death acquired the alias Chepstow, derived from the same Saxon term for commerce that produced numerous Chippings. In Roger's post mortem the description of the borough and its revenue sources included: the tenements in Beachley; rents from shops in the marketplace; a seigneurial prise of ale due from every brew made by each taverner; a similar prise from each boat bringing fresh fish into the port; tolls – estimated worth £20 annually – from the market and from merchandize just being taken through the town; and perquisites of the fortnightly hundred courts and thrice-yearly lawhundreds.

The reversion of the Bigod estates to the king had been engineered by Edward I, who used the same ploy on Roger IV that he had on Gilbert IV de Clare (another beneficiary of the Pembroke inheritance), requiring him in 1302 to surrender the earldom to the king, then re-granting it to Roger and heirs of his body, knowing this limitation on the childless Roger stood to benefit the Crown, and in search of lands with which to endow his own younger sons. In 1310 Edward II divided up the Bigod estates, with large shares going to his half-brothers, Edmund and Thomas. Thomas, known as de Brotherton (1300-38), was in 1312 given the title Earl of Norfolk and post of Marshal of England but, since he was not an heir of his predecessors, he was supposed to relicense any markets for which the Bigods had procured grants. We see this happening only in the cases of Earl Soham (1314) and Harwich (September 1319). In the case of Soham, the fair date was changed from September to Whitsun, but the market left on its original weekday. In the case of Harwich there is no mention of the fair and no change was made to the market day; the most notable feature of the renewal is its reference to Harwich as a borough.

Thomas de Brotherton would go on to license (1327) a market and fair at Earl Stonham, another of the Bigods' manors in Suffolk, almost twenty miles north-west of Harwich; it may have been he who commissioned in the parish church of St. Mary – his fair being held at the Purification of the Virgin – a wall-painting depicting the martyrdom of St. Thomas Becket, after whom Thomas de Brotherton was reputedly named. Stonham was an acquisition of Roger IV and he may not have considered it for development because it was not on a major road, though close to Stowmarket. Through Brotherton's daughter, Harwich descended to the Mowbrays, another family with some history of market development, although mostly before they became Dukes of Norfolk.

The renewal of the Tuesday market licence in 1319 must be seen as part of a larger process of developing Harwich, for in July 1319 Thomas had obtained from his brother a grant of free borough status for his town of Harwich, and for its residents the kinds of liberties customarily associated with burgess status; Brotherton presumably issued a less generic document specifying the privileges of his burgesses, unless he intended to let them choose whatever they wished from any exemplar, which seems improbable. The 1319 renewal lacked the normal licence proviso, raising the question of whether it was strictly a licence or simply royal confirmation of that particular right of a borough; an inspeximus and confirmation by Edward III in 1342, on behalf of one of Brotherton's daughters and co-heiresses and her husband John de Segrave, who received Harwich as part of her share of the inheritance, was charged a fee of two marks, but this was not necessarily a licence fee (the same fee had been charged, a week earlier, for confirmation of the liber burgus grant). Why the market licence confirmation was necessary is not clear, since Brotherton's was granted to him and his heirs, but it may have been to associate Segrave in ownership and ensure the market could descend to his heirs – a shrewd move, since the couple would later divorce and Margaret bear children by a second husband.

Even Harwich's liber burgus charter may have been a confirmation, or enhancement, of an existing situation, for there is reference in 1274/75 to William Fraunc – the surname probably indicative of his status (or that of an ancestor) as a freeman – "a certain burgess of Harwich" [Rotuli Hundredorum, vol.1, p.140] who held the manor of Bradfield, neighbouring Manningtree and about six miles west of Harwich. This does not necessarily indicate any more than that burgage tenure had been put in place by Roger III at some point, presumably a little before he had acquired the licence for a market already in existence; but the number of letters Edward I addressed to the bailiffs of Harwich suggests his administration viewed that port as a town on a par with others – such as Maldon, Yarmouth, or Ipswich – having its own administration, even if answerable to the earl. Furthermore, the earliest surviving court roll for Harwich (1297) shows that it was being separately administered from Dovercourt. Although the calendared final concords for Essex reveal only one instance of a property transaction involving a landless messuage in Harwich, this represents almost the only such transaction related to Harwich, and it may be that property transfers were normally dealt with by the borough court. Yet the marked absence of Harwich from the calendar strengthens the impression that it came into existence as a trading settlement, perhaps in conjunction with, or preceded by, a small fishing community, incorporating little if any agricultural land of significance. Dovercourt as a whole seems not to have attracted the mercantile Londoners who are seen investing elsewhere in Essex real estate, and there are other indications that this part of Essex was not good for grain-growing, although the coastal marshland supported some sheep-farming.

We catch glimpses of William Fraunk of Harwich – or just possibly two successive generations of men of that name – on several later occasions: in 1283 royal commissioners were appointed to investigate his complaint that a chest of his at Dovercourt had been broken into and contractual documents stolen therefrom; in 1285 he and his wife Gunnora acquired a quitclaim to property in Bradfield; in 1286, referred to as a merchant, he was issued a three-year safe-conduct for purposes of trading; in 1294, while in London (where he may have had kin in the wine trade), he witnessed alongside several knights a deed concerning the transfer of the manor of Lawford, Essex; and in 1313, perhaps planning for retirement or death, he was securing his hold on Bradfield for the benefit of his like-named son and acquiring additional properties in Dovercourt with (second?) wife Margaret. According to Wright [The History and Topography of the County of Essex, vol.2, London, 183, p.812] a tenement known as Frankes, incorporating a shop, was at later date donated to Dovercourt's church. Although William must be considered exceptional rather than typical, that Harwich could produce a merchant trading overseas, accumulating enough wealth to invest in large properties, and rubbing shoulders with the Essex gentry, surely reflects well on its economy.

The new port at Harwich was quickly integrated into the coastal administration system, in regard to customs collection, border policing, naval service, and management of foreign relations. The late thirteenth and early fourteenth centuries in particular saw the bailiffs of Harwich often being instructed, or sometimes reprimanded, by the king regarding seizure of ships, goods of foreign merchants, or unauthorized exports. Edward I used Harwich not only as a transit point to the continent but also as the location of a town-planning conference, while Edward II had supplies and troops shipped from there to the Scottish war. As regards commerce, Harwich seems to have been frequented mainly (and unsurprisingly) by ships coming from Holland, Zeeland, Friesland, Flanders, Hainault, and Normandy, while by mid-fourteenth century Hanseatic League vessels are also in evidence; documentary evidence to this effect is supplemented by ceramics finds at Harwich, which show a high proportion of imported pottery, mainly from France and the Low Countries.

In the late thirteenth century Harwich's port was attracting about as much traffic as Yarmouth, although the latter's residents were much more involved in ship-owning than those of Harwich, to judge from royal demands for naval service. One customs controller's account [statistics tabulated in Nicholas Amor, The Trade and Industry of Late Medieval Ipswich, PhD thesis, University of East Anglia, 2009, p.92] shows that between February 1397 and September 1398 there were 45 arrivals and 37 departures of cargo-bearing ships at Harwich, a figure exceeding the numbers at Colchester and Maldon and exceeded (though not greatly) by the number at Ipswich. At those dates cloth was the predominant export – wool being largely restricted to Ipswich – its quantity being roughly at par with that exported from Ipswich and Colchester, though more fish was exported through Harwich than through the others. Imports were a mixed bag, with wine (the dominant item at the other ports) surprisingly absent – despite other evidence showing that customs on foreigners' wine imports were collectable at Harwich and that wine fleets sometimes assembled in that port for their safety-in-numbers ventures to Gascony – but with dyes, salt, grain, fish and furs being the most notable in terms of quantity or value; again, other evidence suggests that Flemish cloth must have been, at times when England and Flanders were at peace, landed at Harwich.[J. Richardson, ed. The Annalls of Ipswche, Ipswich, 1884, p.68].

In addition to the overseas trade, coastal shipping between north-eastern ports and London, even if mainly using Harwich as a stop-over point or safe haven, is evidenced by archaeological finds there of pottery produced at London and Scarborough, and exemplified by complaints, in 1273 and 1294, by merchants of Newcastle-upon-Tyne and Berwick about unwarranted seizures of their cargoes at Harwich. In 1265 a complaint by John de Gisors, a leading London victualler and vintner who owned a waterside manor in Essex to facilitate his coastal trade, implies that Harwich men might also indulge in a little piracy or privateering, a problem still evidenced in the fifteenth century; foreign ships anchored at Harwich were also considered fair game by the Cinque Ports seamen, who regularly sailed coastal waters on the lookout for prizes. It was Harwich's vulnerability to attack that enabled it to obtain a murage grant in 1338, providing a lever for Harwich to challenge Ipswich's claim to a monopoly over toll collection in the Orwell; though Edward III revoked the grant following Ipswich's initial complaint, a renewed complaint in 1340 alleged that Harwich's bailiff had continued to collect customs that ought to belong to Ipswich. Despite Ipswich's jurisdictional claims, the king found it advisable to issue murage grants again in 1352 (along with licence to crenellate), 1378 in the context of an invasion scare, and finally in 1451, just a year before Harwich, its defences still incomplete, actually fell victim to a night attack by French forces. Other sources of income for some local residents must have been the business of provisioning ships using the port, including those pressed into naval service, and ship-building activities, although the latter are not in evidence until the fifteenth century.

Such was the opportunistic environment that assisted men such as William Fraunk to rise in socio-economic status. William's fellow-burgesses are less in evidence, although we hear of a Ralph Stace of Harwich who in 1301 sold a pipe of wine to a Colchester taverner and in 1321 lost £50 worth of goods when his ship, captained by Richard Stace, was boarded by foreign pirates while anchored off the Yarmouth coast. In 1364 Harwich merchant Robert Gatman was authorized to ship ten tuns of ale from Ipswich to Flanders. Harwich does not seem to have produced many standout burgesses – nor is 'Harwich' much in evidence as a surname – in part because its population was relatively small, while those who did prosper sometimes moved on to the richer clime of Ipswich. Such a one was Richard Felawe (d.1483), first mentioned in 1422 as a Harwich merchant, associated in some fashion with Ipswich merchant John Caldwell. He evidently rose to the top of local society before moving to Ipswich and selling up his Harwich property in the early 1440s; there he was quickly adopted into the town council and served multiple terms as bailiff between 1448 and 1475, as well as holding the royal posts of customs collector or controller for much of the 1450s and '60s. But he retained ties to his original hometown, and in 1452 he became involved with a small group aiming to push through the project to erect Harwich's walls, obtaining royal licence to export 2,000 woollen cloths from Ipswich and apply to that project the customs due therefrom. A Yorkist, Felawe was a servant of Sir John Howard, who would become Duke of Norfolk, though this affiliation necessitated royal pardons at several points in his career. Richard committed some unscrupulous acts during his life, and it may have been due to heavy conscience, genuine social concern, or a mix of both, that in his will he provided for establishment in Ipswich of a school, where children of poor families were to receive free education, and an almshouse for the sick. Either he or, perhaps, a like-named nephew was bailiff of Harwich ca. 1483; Richard's only known offspring was a daughter, who married into the Ipswich branch of the Fastolf family.

Yet despite a scarcity of merchants prominent on a national scale, by 1343 the Harwich community had enough wealthy residents that the king could name nine Harwich ships capable of crossing the Channel, their masters including a William Stace and Richard Stace; later that year one of those ships, carrying 56 tuns of wine and other goods from Aquitaine to Normandy was captured by Spanish pirates, while in 1342 a tenth Harwich ship, carrying 170 tuns of wine and other goods from Bordeaux to England, had fallen prey to the Spaniards. After the French assault of 1451, Harwich's capacity to accommodate sea-going vessels may have been reduced for a while [Amor, op.cit. p.204]. But in the post-medieval period its role as one of the most important of England's North Sea ports, with both naval and civil functions, would be recognized by investment in strong fortifications, partly replacing and partly reinforcing whatever had been put up in the Late Middle Ages; these fortifications were again superseded by new defences after Harwich became a naval shipyard. As a borough, however, Harwich's constricted site kept it relatively small in size; consequently, the medieval street-plan has survived well, even though the town's buildings were largely replaced in the post-medieval period, though a very few retain medieval timber-framing, now hidden behind later facades.

The street layout was inserted into the spit at the end of the promontory and its only land access was the road from Dovercourt, approaching from its south side – here was built the main gate through the medieval walls; to the east, west, and north of Harwich lay the sea. The main stretches of the defensive stone wall protected the east and south-east sides of the town, with wooden palisade on the northern side and bank/ditch to west and south-west. One consequence of the confined site was that houses were tightly packed and plots incorporated only small backyards; however, there were a few large properties, including the earl's townhouse and a merchant's house with wings around a central courtyard and masonry cellars beneath. The grid-pattern street plan incorporated three main streets oriented roughly north-south and named East Street (now King's Head Street), Middle Street (now Church Street), and West Street. These were crossed, at right angles, by several east-west lanes, thus dividing the site into blocks. To the west of West Street was mostly land where residents grazed their livestock, although archaeology has shown that parts were built on as early as the thirteenth century. At the north end of the main streets was the stone-built quayside, lined with stone warehouses, which were incorporated into the defences. At the north-east corner of the town a 'castle' (a large tower) was incorporated into the wall, built on a plot donated by the earl in the early fifteenth century. Flooding and coastal erosion created problems for the residents, with some reclamation evidenced as well as fourteenth-century demolition of some Middle Street buildings, followed by dumping of sand on top to raise the ground level.

No provision was made within this town plan for a dedicated marketplace. The market was probably held in one or more of the streets, though it remains uncertain which. West Street was the widest of the three main streets, with a slight bulge around the mid-point of its length. Middle Street has a slight curvature, possibly dictated by the chapel (assuming the later parish church to have been built on the same site); the street widened after it had passed the chapel. The chapel likely had the same dedication as the later church, to St. Nicholas, patron saint of traders, which would lend support to the characterization of Harwich as a trading community. The likelihood of the dedication being to St. Nicholas is bolstered by the selection of the date of the fair licensed in 1253, even though the earl sensibly avoided the main festival of that saint, occurring in the commercial off-period of December; for he also avoided an overt connection of the fair with any other saint, preferring to associate it with the Ascension. This timing placed it close to the lesser festival of the Translation of St. Nicholas (May 9) and in fact, in 1252 – when, we might posit, the earl formulated his plans for the market/fair licence – that date fell on the same day as the Ascension; the unusual length of the fair (ten days) may have been to increase the number of years when that saint's day would fall within the scope of the fair. East Street, which only began north of the chapel site, had more the narrowness of a lane until crossed by Market Street, after which it widened along the stretch leading to the quayside; this was what became known as the High Street.

Another candidate for the location of the medieval market is the cross-lane known as Market Street (the site of the post-medieval market), which ran from Middle Street to the eastern and largely undeveloped area of shoreline, where there was a gateway incorporated into the town wall; Market Street was originally wider before fronting buildings encroached on it. In the block flanked by High Street and Market Street, was the earl's townhouse; the chapel was a little further south. The character of the medieval market, in terms of goods principally traded, is unknown and there is no indication of occupational diversity at Harwich greater than any small market town. Harwich's fortunes depended on its access to the sea.