Saffron Walden has been described as "the best surviving Market Town in Essex" [Maria Medlycott, Saffron Walden - Historic Towns Assessment Report, Essex County Council,1999 p.10], partly because its medieval street-plan is well-preserved, as is a relatively high proportion of its medieval fabric (notably timber-framed houses). It is also relatively well-documented, despite manorial records prior to 1381 having been destroyed in the Peasants Revolt, and (for a small town) relatively well-investigated by archaeologists. But all this has not prevented interpretation of the development of Walden from being somewhat speculative and debated.

Walden is situated in the far north-west region of Essex, in the upper Cam valley so that it is comparatively distant from London (43 miles away); Cambridge is the nearest town of any significance – though not especially prosperous compared to other large towns – 12 miles to the north. But Walden lay close to a route between London and Cambridge (following a chain of river valleys) which, a few miles north of Walden intersected the Icknield Way, heading to Norwich. Perhaps equally important, it was situated in a border region between rich grain-growing areas, to the north-west, and more wooded, pastoral areas to the south-east, making it well-placed as a point of exchange for the products of each area. However, the growth of a medieval population nucleus beyond the main valley and on a hillside would pose a challenge to its development as a market centre. A relatively large number of market towns emerged in this part of Essex and in closely neighbouring Hertfordshire and Cambridgeshire, though (geographically and chronologically) the most immediate competitor to Walden was Newport, a few miles south, whose market pre-existed that at Walden.. The closest other market settlements were at Great Chesterford just to the north-west, Wendens Ambo a similar distance south-west, and Ashdon somewhat further to the north-east, all emerging after Walden's market had been instituted. Besides Newport, Walden faced little other market competition in the region for some generations.

Walden was one of the manors allocated by the Conqueror to Geoffrey de Mandeville (d.1100), paternal grandfather of the like-named first Earl of Essex (d. 1144); most of those estates, and the most valuable of them, were in Essex. However, Walden, Great Waltham (the most valuable property), and Sawbridgeworth (Herts.) were pledged by Earl Geoffrey's father, William, towards payment of a huge fine for dereliction of duty as constable of the Tower, and, pending payment, were given by the king (ca.1103) to Eudo Dapifer, William's father-in-law, reverting to the king after Eudo's death. Geoffrey was eager to win back the lands of his father (whose widow had remarried and produced a son as an alternate claimant) and maternal grandfather.

At the time of Domesday, Walden was a fairly large village within a manor of rising value, pasturing large numbers of sheep and goats and with enough woodland to feed an even larger numbers of pigs. Its fertile land received water from tributaries of the upper Cam and from springs penetrating the chalk underlying Walden's terrain. It was the hinterland's agricultural wealth that provided the basis for development of a market centre at Walden. This wealth was exploited seemingly continuously from at least the Iron Age. Archaeology has shown that a small Romano-British settlement existed there: possibly an outpost of a fort/town at Great Chesterford where a Cambridge-London road, following the Cam valley, crossed the river. This was succeeded by an initially modest Anglo-Saxon settlement, in and around a tributary valley, associated with a cemetery in use from seventh to at least ninth century and perhaps up to the early thirteenth, judging from pottery finds there; it has been assumed the Christian burials in this cemetery meant the presence of a church and, although neither such a building nor any priest is mentioned in the Domesday entry, an area where burials have not been found might represent the site of a church. Part of the through-road was diverted at some point, possibly as Walden began to take shape in the post-Roman period. [S.R. Bassett, Saffron Walden: excavations and research 1972-80, Council for British Archaeology Research Report 45 (1982), pp. 11-4].

It was probably in the early 1140s – though this remains a matter of historical debate – that (again, probably) Earl Geoffrey erected, or at least completed, a motte-and-bailey castle at Walden to the north-east of the Saxon settlement site, atop a chalk promontory known as Bury Hill – a name that makes us wonder if earlier fortifications might have been there, though no archaeological evidence of such has been found, other than worked flints discovered near the foot of the hill. It is even less certain whether the stone keep was the work of Geoffrey or of one of the two sons who, in turn, succeeded him. Adjacent, and at a central position within an ovoid outer bailey that followed the contours of Bury Hill, a church – or perhaps just a chapel dependent on the Saxon church – dedicated to St. Mary was built, and in that vicinity, between the inner and outer bailey fortifications, there could have been some residential tenements; this area is generally considered a planned town [e.g. Carenza Lewis and Catherine Ranson, Archaeological Excavations in Saffron Walden, Essex, 2013, Access Cambridge Archaeology, unpublished report, 2013, p.17; John Schofield and Alan Vince, Medieval Towns, 2nd ed. London: Continuum, 2003, p.53], although evidence for this interpretation is largely circumstantial. If there existed an earlier church associated with the older Anglo-Saxon cemetery, St. Mary's must, at date unknown, either have been a rebuild on a new site or have superseded it as the parochial institution (something similar being seen, in regard to St. Michael's, at Braintree) and as the location of the community's cemetery; the oldest surviving fabric in St. Mary's dates to the later thirteenth century, but there are indications of an older and smaller church on the site. Bury Hill rose between two streams (Kings Slade and Madgate), and enabled the castle to command a valley leading to the River Cam, about a mile to the west.

It was at the confluence of those streams, just west of Bury Hill, as the River Slade (which later joins the Granta/Cam), that the medieval nucleus of Walden – not evidently the same site as the Domesday settlement, which is more likely to have been on the Romano-British site – would develop [Bassett, op.cit., pp.2, 14]. This nucleus is still signified by the parallel Castle Street (north) and Church Street (south), which mark the extent of the ditch-and-rampart inner bailey before, west of the church, connecting to the Bridge Street section of the north-south through-road. Whether Castle and Church Streets developed from trackways around the bailey or were deliberately laid out as part of a castle-town is uncertain, but the latter seems probable, given that they were encompassed within the outer bailey, that other developments (outlined below) suggest intentional development of Walden, and that the orientation of the church hints at a planning relationship with the two streets. Geoffrey's strategy with the castle and its associated civilian elements was to defend his estates and the communications routes between them, make of Walden a market settlement, and see what he could leverage out of the power-struggle between Matilda and Stephen in order to restore the family fortunes.

Geoffrey II had already (ca.1136/43) founded in the western part of his manor, near the confluence of a tributary with the Cam and (after a minor shift in location) where several roads met, a Benedictine priory dedicated to St. James and St. Mary, part of its role being to service travellers; in 1190 it was promoted to an abbey. This too attracted settlers, in a hamlet which acquired the name Brook Walden; by 1400 there were some 51 cottage plots, although only a single shop is heard of. Geoffrey endowed the priory with Walden's church, among others; in approving the foundation and endowments, Stephen also granted the monks a short fair at the festival of St. James, though the date of the grant is uncertain. The monks complaining of having no market close at hand, Edward I granted (1295) the abbey its own market, on Tuesdays, at its manor of Walden St. Mary. The monks' dubious concern, given the proximity of Saffron Walden's market, was perhaps on behalf of their tenants and indicates more a desire for revenues from market activity than for convenient shopping. No objection from Saffron Walden's market is known, but the Mandeville male line was by then extinct and their Essex estates had come, through marriage, to the Bohun earls of Hereford and Essex. Walden Abbey's market seems to have been held in one of the streets flanking the abbey precinct, widened for the purpose and also later known as High Street, with regularized plots laid out along either side, and a Back Street at rear of some of these [Bassett, op.cit., p.22].

Using his military support as coin, Geoffrey II negotiated alternately with Matilda and Stephen, thereby gaining the earldom (from Stephen), the office of sheriff in Essex, Hertfordshire, Middlesex and London (from Matilda), restoration of family lands, and other concessions. One of the these (by Matilda, ca. 1141 – the dating of the charter being disputed) was permission

"to remove the market at Newport, with all tolls, passage, and other customary impositions, in the fullest form they existed, previously belonging to that market, to his castle at Walden, and that the roads serving Newport that follow the river may be redirected from their normal courses towards Walden, upon penalty of forfeiture to me; and the market at Walden shall be on Sundays and/or on Thursdays, and that a fair may be held at Walden beginning on the eve of Whitsunday and lasting the entire week of Pentecost." [Regesta Regum Anglo-Normannorum 1066-1154, ed. H.A. Cronne and R.H.C. Davis, vol.3 (1968), p.99; my translation]

This shrewd move by Geoffrey thereby increased the value of Walden and hobbled (at least temporarily) a nearby competitor, not only by depriving Newport's market, which belonged to the Crown, of much of its profitability, but also by requiring traders to take the road to Walden instead – Bury Hill being a little distant from the main road through the Cam valley, so that some intervention was necessary – or face confiscation of their merchandize. Both the abbey and castle markets are likely to have drawn some residents away from the older Saxo-Norman settlement. The inquisition post mortem on earl John de Bohun in 1336 refers to a Saturday market at Walden – perhaps a shift from a Sunday event, unpopular with the Church – and to a fair on the Nativity of St. Mary (September), a shift perhaps better suited to availability of produce; Elizabeth Allan [Chepyng Walden/Saffron Walden, 1438-90: A Small Town, Ph.D. thesis, University of Leicester, 2010, p.43] has suggested that a Pentecost week fair licensed in 1189 for Royston (Herts.), some dozen miles west of Walden, might have influenced the change, but there is no sign of a legal challenge from the last Mandeville earl, who died that same year, or his successors (but then, nor is there record of a required royal approval for the fair's change in date).

Once settled on the throne, Stephen, distrusting the ambitious and now-powerful Earl of Essex, had him arrested in 1143 and forced him to surrender Walden castle, not yet completed; but Geoffrey responded by going into open rebellion in Cambridgeshire, during which he attempted to control the road south to Walden. His death in 1144 brought that episode to an end, but the only partially successful efforts of his son (by a de Vere mother) and successor, Geoffrey III, to preserve his father's gains led to the castle being partly demolished in 1157, although later evidence points to some continued usability, if not complete restoration.

At this period, Walden's fair was presumably held in the open area known later as the Feyrecroft, and the market may, Bassett conjectured, have been held in and around Bridge Street, which later continued as the High Street. These streets were components of the through-road diverted towards Walden (as per the 1141 grant) about a mile north of Newport and again on the other side of Walden, so that it would swing through the outer bailey, rather than the Anglo-Saxon settlement; this provided for a comparatively gentle ascent up Bury Hill, rather than the daunting climb (for a burdened pedlar or cart) that a closer and sharper deviation of route would have necessitated. The posited market area extended between Bridge Street's junctions with Castle and Church Streets and continued eastwards as far as the church, as well as westwards a rather shorter distance – the topography hinting at a narrow lane connecting Bridge Street and church, midway between and parallel to Castle and Church Streets; numerous metal artifacts found in the area between Castle and Church streets would be consistent with market trading.

This location would have placed the market within the protection, or control, that the outer bailey provided, while the church was positioned to serve both the castle and the market settlement. Remains of a stone cross, suspected as being one designating the market, were embedded in the church wall during a rebuild following later relocation of the marketplace. Castle, church, High Street and market thus can be imagined as elements of an intentional and coherent plan to steer London-Cambridge traffic – even though the road connection to London was no longer a major route – through Walden, where it could make use of the market and be taxed by the earl's officials. Furthermore, it has been observed that tenement frontages facing onto that postulated marketplace – that is, along the north side of Castle Street, south side of Church Street, and the intra-mural High Street – suggest use of a consistent measure (30 feet, or multiples thereof), so that Saffron Walden appears to have begun as a planned castle-town [Bassett, op.cit., p.18-20], or was at least proto-urban. Pleshey would be similarly developed by the Mandevilles, and its castle also slighted in 1157, but later refortified. Which of the two centres, if either, was considered the caput of the family holdings in Essex and Suffolk is unclear; the strategic position of Walden near the Cam valley route, and acquisition of market rights for Walden at the expense of Newport, must have made Walden particularly valued for some decades, but the restoration of Pleshey's castle in the 1180s probably saw the family transfer its main residence there, despite that the site was less advantageous as regards commerce.

Other than at Pleshey and Walden, the Mandeville earls are not associated with many market foundations. By the same charter allowing him to transfer Newport's market rights to Walden, Geoffrey II de Mandeville was granted a Thursday market and a fair around the festival of St. James at Bushey (Herts.); a moated manor-house was built there around the same time, but no castle was felt necessary. Bushey was another of the manors that came into Mandeville hands following the Conquest, and was well-situated on the London to Watford road, possibly Roman in origin. At the time of Domesday it was a small village focused around the parish church of St. James (itself suspected of possibly having replaced, in early or mid-thirteenth century, a Saxon chapel) and adjacent village green. But subsequent development was along the through-road (Bridge/High Street) east of the green, whose sides – the north in particular – are fronted by a limited number of burgage-type plots – though this might have been a late medieval or post-medieval growth phase – after which settlement petered out. The extinction of the Mandeville male line in 1227 brought Bushey back to the Crown, but Henry III granted it in 1270 to David de Jarpenville, who promptly renewed in his own name the market rights (which, the record is at pains to note, he had not yet used after acquiring the manor); the Jarpenville family had, since late twelfth century occupied Bushey as Mandeville tenants, and one of David's ancestors is credited with building (1166) Bushey's church and obtaining its parochial independence from Watford. Bushey manor had been broken up into sub-holdings by the close of the Middle Ages. Although Great Waltham was a valuable Mandeville manor, and the family built the parish church (ca.1100), they did not invest in a market licence there, perhaps because it was too close to Chelmsford.

After the death (1189) of Geoffrey II's younger son, William de Mandeville, the direct male line ended and the family estates, and later the earldom of Essex, passed, through a female line and then by marriage, to Geoffrey Fitz-Peter, a man of modest socio-economic background but evident ambition and ability, for he worked his way up the administrative ladder under Henry II and his sons, and made a good marriage to Beatrice de Say, grand-daughter of a Mandeville earl; he gained influence and won royal favour particularly through his service in shrieval posts and as Chief Justiciar (from 1198 to his death in 1213). In 1200 King John rewarded him with permission for a market and fair at Kimbolton (then Hunts.), situated near the borders of Northamptonshire and Bedfordshire; the layout of the village, a hundredal centre, was reorganized around a burgage-fronted marketplace positioned between the village church and a newly-built, though small, castle. Two months later, Fitz-Peter was given a market licence for Amersham (Bucks.), an early Mandeville possession, and again may well have introduced a burghal component, for later in the century there are various indications Amersham was considered a borough, with burgage-type lots along one side of the High Street (the opposite side belonging to a separate manor), a widened stretch of a road from London that traversed the Chilterns, and the location of Amersham's marketplace [Buckinghamshire County Council, Amersham Historic Town Assessment Report: Final Consultation Report, English Heritage, 2009, passim]; in 1363 this market was reckoned to generate 10s. of comital revenue from tolls. That grant was followed in 1204 with a licence for Fitz-Peter to hold a market at Folkestone, on the Kent coast, though his son and successor divested himself of that property, and then in 1207 licence for market and fair at Moretonhampstead (Devon). This last was a village on the road across Dartmoor from Exeter to the borough of Tavistock, at its junction with a road connecting the market towns of Okehampton and Bovey Tracey; the market was held in a large central area, beside the church, formed by a convergence of roads, and there is some indication of a possible burghal component. Geoffrey Fitz-Peter's sons adopted Mandeville as their surname and succeeded to the earldom in turn. In 1220 the younger, William Fitz-Geoffrey de Mandeville (d. 1227 without heirs) complained that his Moreton market was being harmed by one at Chagford; William's lawyer argued that the Chagford event was not a proper market, but only a wake at which bread and ale were sold, to which Hugh de Chaggeford responded that his market had been in existence for a hundred years and involved the collection of toll and stallage. The resolution to the legal battle is unknown, but there is no indication Chagford's event was suppressed.

The Gazetteer of Markets and Fairs also identifies as a Mandeville foundation a market, licensed with a fair in 1281, at Thorpe Mandeville (Northants.), a small village that in Domesday was simply referred to as Thorp (meaning 'village'); a market there would likely have been held at the junction (lying between church and manor-house) of a minor road with a through-road that served as a drovers' route between Banbury and Northampton. However, Mandeville here is a corruption of Amundeville and the grant was perhaps less to the manorial lord, Richard de Amoundeville, than it was to his wife, a member of the family of the Fitz-Alan earls of Arundel.

The Mandeville development strategy at Walden may have worked well enough to create some population pressure on the space available within the outer bailey. But the topographical arrangement described above presented obstacles to expansion as Walden and its market attracted new settlers. There was limited space within the outer bailey, church and castle inhibited spread westwards, while the abbey's gradual expansion of its site and adjacent parkland limited the scope of settlement in that vicinity. This could explain why a new area was planned and laid out, accommodating existing topographical features, downslope (south) of the castle, church, and posited market complex.

However, the date of this expansion remains uncertain. It may well have been during the lordship of one of the Bohun Earls of Essex, descended from Henry de Bohun, Earl of Hereford and husband of Geoffrey Fitz-Peter's niece, Maud Fitz-Geoffrey, herself a descendant of the sister of Geoffrey II de Mandeville. The Bohuns already had a little experience with market towns: at Trowbridge (Wilts.), licensed by Henry in 1200, while Humphrey IV de Bohun or his like-named son licensed a market at Huntington (Herefords. 1257), and later Humphrey VII, 4th Earl of Hereford and 3rd of Essex, renewed the Camvills' market licence for Fobbing (Essex, 1318) and took out licences for Pinchbek (Lincs., 1318) and, with his wife (a daughter of Edward I), for Enfield (Middx., 1303). Humphrey VII probably came into possession of the Essex manor of Great Baddow, neighbouring Chelmsford, through his marriage, for the last Bohun countess had dower rights therein (1373); but its market seems to have been founded by Edward I (1306), perhaps as a favour to his daughter, for no licensee is specified in the grant and no anti-competition proviso is in the precept to the sheriff to have the market proclaimed and held. Linton (Cambs.), six miles north of Walden and near the Essex border, situated where a road to Newmarket crossed the Granta (tributary of the Cam), was another manor that came within the Mandeville orbit, but earl Humphrey IV de Bohun in 1284 surrendered his rights in Linton and Sawbridgeworth to rival William de Say, scion of another female-sprung branch of the Mandevilles, in return for William relinquishing his claim to Walden and other Mandeville-Bohun manors. An earlier William de Say had already licensed a market (1246), and introduced a burghal component, at Linton, while Geoffrey de Say had licensed one (1222) at Sawbridgeworth, also close to the Essex border and at a road/river intersection, although its day had to be changed following a complaint from Hatfield Broad Oak; there are indications of a planned layout around Sawbridgeworth's crossroads marketplace. Another Mandeville manor in Cambridgeshire, Chippenham, was donated to the brothers of the Hospital of St. John of Jerusalem and it was they who licensed a market there (1226).

On the whole, and with the possible exception of Geoffrey Fitz-Peter, neither the Mandevilles nor their Say and Bohun successors can be considered prolific founders of either markets or towns, despite their estates being numerous and widespread. Even the Bohun earldom of Hereford was not associated with such foundations, apart from Huntington, although the family had limited seigneurial interests in and around Gloucester and Hereford – both urban well before the Conquest – and the court of the Honour of Hereford was based in the former. Similarly, Hoddesdon (Herts.), a village situated on a London-Cambridge route, had come into family hands before the death of the last Bohun earl and served for a while as the administrative base of that earl's Honour within Hertfordshire (though this was at Hertford itself in the time of his predecessor); yet Bohuns had no hand in acquiring the licence granted its market in 1253, even if much later Henry Bourchier, as Earl of Essex, was owner of the market. The last Bohun earl's young widow, Joan Fitz-Alan – who did not remarry after her husband's death (1373) and, as Countess of Hereford, retained control of much dower property into the reign of Henry V, her grand-son – was known for encouraging cloth-finishing and related industrialisation on some of her estates; there is no evidence, however, that Walden benefited, for no fulling mill is known to have been built there.

The dating and character of the extension to the original castle-town at Walden is based partly on a charter issued to residents by one of the Bohun earls. This was once thought to have been Humphrey IV de Bohun, in 1236; but, during the interregnum between the Mandeville and Bohun lordships, Walden was mortgaged to the Archbishop of Canterbury (who farmed it out to Walden Abbey) and it was not until 1239 that Humphrey acquired the earldom of Essex and its estates. This burden on the manorial revenues – a repayment of £100 a year being due – could have been motivation for an attempt to increase their value by introducing a new market settlement. However, the charter has now been re-dated to 1300, which places it during Humphrey VII's time – in fact shortly after he inherited his earldoms, as a young man. Yet a reference to "Waleden Mercati" in 1295, distinguishing it from the "Castel Walden" mentioned 1285 [Ernest Kirk, ed. Feet of Fines for Essex, vol.2 (1913), pp. 49, 73], could indicate that the new marketplace was in existence prior to the charter. The Bohun charter hardly has the scope of a royal grant of liber burgus – the earl being in no position to concede regalian rights – but granted freedom from the feudal dues of heriot and relief (essentially an inheritance tax, that an heir had to pay to enter into property of the deceased), which was a step in the direction of burgage tenure; yet other feudal customs, such as labour services attached to at least some land-holdings, and chevage for villeinous tenures, remained in force. The charter also confirmed any liberties and customs exercised in the past, but this generic statement cannot in itself be taken as evidence of burghal conditions earlier in the century, or in the castle-town of mid-twelfth century.

At some point following the death of the last Bohun earl, Walden, along with the rest of what was now known as the Honour of Mandeville, became part of the duchy of Lancaster, John of Gaunt (on behalf of his son Henry Bolingbroke) and his brother Thomas of Woodstock having vied to acquire the Bohun estates though marriages to the earl's daughters and co-heiresses. In 1402 Bolingbroke, now Henry IV, confirmed the liberties to which all towns within the duchy – among them Walden – had the right. These included exemption from tolls throughout the duchy, and that the burgesses (as opposed to manorial tenants as a whole) could elect one of their number as a bailiff to administer the market and collect fines from the market court, operating under piepowder procedure to resolve commercial disputes, although more routine market matters remained within the purview of the leet court (see below).

The new town – if we may so characterize it, though the evidence is ambiguous – had a rectilinear grid pattern of new streets These streets, together with the twelfth-century settlement around Bridge Street and church, and the older Saxon settlement, were largely encompassed within, and separated from the abbey park by, what was called 'the great ditch'. This was an apparently continuous bank/ditch construction – the ditch about 4 m. wide and 2m. deep, and the adjacent bank at least 7m. wide and 2m. high – extending west and south from the castle's outer bailey, at least parts of whose enclosure (now made redundant, except for a northern part incorporated in the new enclosure) were levelled/back-filled, thus providing more area for residential development. Not quite square in shape, the great ditch enclosed an area of about 20 hectares; it was not so much a fortification – and indeed was itself later infilled – as a boundary demarcation and method to control the flow of commercial traffic into the town, being accessed by entrances across the ditch on each side, including of the High Street on the northern and southern sides.

But the market straddling Bridge Street – which was now extended south into what became the High Street proper, was superseded by a new marketplace in an almost central position within the ditch-defined town, in the area between George Street and Church Street. Laying just beyond the south gate of the outer bailey, the new marketplace might have been the first element developed [M.R. Petchey, "The archaeology of medieval Essex towns," Archaeology in Essex to AD 1500, Council for British Archaeology Research Report no.34 (1980) p.116]. One of the new east-west streets running off the High Street, now known as King Street but earlier as Market End Street, was widened for much of its stretch before opening out into a large (24 perches square) space ending at a new north-south road which became known as Market Street, and connected (possibly at later date) to Church Street by what became known as Market Hill. The streams flanking Bury Hill, after converging, passed along one side of the marketplace, but this was culverted in the post-medieval period.

Intermediate between King Street and Hill Street is Market Row, a lane whose adjacent buildings may indeed fossilize blocks of market stalls that, in the fourteenth century, were becoming more permanent structures. An Essex fine of 1410 conveyed an extraordinary 22 shops in Walden, though the character of these structures cannot be determined – some may have been incorporated in the five messuages conveyed, some may have been stand-alone structures in the marketplace; in deeds from the early fifteenth century we regularly hear of shops in the marketplace, sometimes clearly distinguished from stalls, and a conveyance of 1471 concerns a market stall with walls erected on every side [ERO D/B 2/2/20]; but it is also clear that shops were not restricted to the marketplace. Subdivision and amalgamation of shops and stalls contributed to the process of transforming the marketplace, and in the post-medieval period the distinction between stalls and shops seems to have been relinquished. This infilling, perhaps slowed or even interrupted by the economic and health crises of the second half of the fourteenth century, eventually became, in the post-medieval period, the fate of the entire southern half of the marketplace and of Market Hill, and contributed to the appearance of a grid pattern of streets by giving rise to alleyways between the infill buildings, with names such as The Butchery, Drapery, Cordwainers Row, Butter Market, and Pig Street. Yet, in the medieval period there remained enough open space that, in 1400, the rows of stalls (which could be conveyed by sale, gift, or lease) hosted fishmongers, butchers, poulterers, traders in cloth and leather goods, and the mercers who became increasingly prominent within Walden society in the Late Middle Ages, while grain was sold in a central area, referred to as the cornmarket; a tollhouse or market hall occupied the centre spot and, in the Tudor period, served as a communal moot-hall and a meeting-place of the Holy Trinity Gild, a social institution underlying the political power-structure of Tudor Walden. That the marketplace was paved with gravel in the thirteenth century, and perhaps later re-paved, is suggested by minor excavations within the space, which uncovered a series of stone surfaces. The seigneurial malt mill stood on the north side of the marketplace, while the course of the Slade valley defined the marketplace's southern edge (now Hill Street), though this valley had been subject to reclamation and colonization from about the opening of the thirteenth century, presumably because of population pressure, and the watercourse itself was subsequently culverted as Hill Street was built up.

Following the Bohun addition to the manor of Walden we find (by 1328) that the settlement had become known as Chepyng Walden – an indicator of its commercial role; in a deed of 1511 we have reference to "a shop situated in the market place or cheap of the town of Walden" [ERO D/B 2/2/31]). The name Waleden ad Castrum, encountered in a Bohun deed of 1345 [ERO D/B 2/3/56] and one drawn up at Castle Walden in 1302 [ERO D/B 2/4/6], as well as an Essex fine of 1285, may have pertained to the older castle-town neighbourhood, although possibly only a local differentiator. It may be these were considered sub-manors and had some degree of administrative separation (e.g. as regards transfers of property), but the name Walden continued to be the predominant usage to refer to the entire manor, vill, or parish. The abbey's area of jurisdiction, focused on the cottagers of Brook Walden (although the abbey also held a little property in Chepyng Walden), remained a separate manor.

The parish church underwent some expansion around the mid to late thirteenth century, an initiative that could be linked to plans to accommodate population growth. Whether this was at the expense of Earl Humphrey or of the local community we do not know; certainly by the 1430s the parish community was prospering enough to finance significant improvements to the church. Bassett [op. cit., pp.25-26] argues that much of the newly-developed area south of Church Street, including one and perhaps both sides of the High Street, were divided into insulae 12 perches square. More recent excavations have suggested that insulae such as those theorized by Bassett may also have been laid out along the eastern side of the great ditch [Lewis and Ranson, op. cit., p.38], although this does not help us to date the project.

Bassett's theory has not gone unchallenged [David Andrews, Charles Mundy and Helen Walker, "Saffron Walden: the topography of the southern half of the town and the marketplace", Essex Archaeology and History, vol. 23 (2002), pp.221-73.] and an alternative has been advanced that the town ditch, grid street pattern, and new market area were part of the planning initiative of the 1140s. There is some very slight archaeological evidence that could support this dating. However, one of the main arguments of this interpretation – that conditions at that time required defence of the settlement – ignores that the outer bailey provided just that. Similarly, the argument that large defensive enclosures were unusual during the post-Anarchy period forgets numerous urban initiatives intended as much to define as to protect boroughs. If additional protection was felt necessary for Walden, this might have been provided (for example) during the tenure of earl Humphrey VII, who was part of the baronial opposition to Edward II and the Despensers and by 1322 in open rebellion, or even in the time of Humphrey VI who, with ally the Earl of Norfolk, had almost come to the point of rebellion against Edward I. A castle-side civilian settlement protected by an outer bailey was a design approach more common in the twelfth and early thirteenth centuries, whereas additional town enclosures of the size of Walden's great ditch were not; its enclosure is unlikely to have been warranted until after a period of population growth fuelled belief that a large new residential area could be developed. The current dating of Walden's charter suggests that an insulae-based new town layout might have been influenced by the king's own initiative at New Winchelsea in the 1280s. It could perhaps be associated with gradual efforts to rehabilitate Walden's castle, culminating in a licence to crenellate (1347), though whether this was for the keep, being restored as a hall and accommodations, or a manor-house within the inner bailey, is not clear and – since it was a blanket licence for several Bohun manors – we cannot be certain it was even acted upon at Walden.

If Bassett's argument is correct, the new marketplace was assigned four insulae. Whether the other chequers of the spatial organization were immediately sub-divided into tenement plots is doubtful, as modern property boundaries do not show much by way of rows of standardized burgage plots. It was the High Street and new market neighbourhood that attracted settlers – men such as Richard le Chapman, who in 1351 was described as of Thundersley (a village just south-east of Walden), when his brother Simon gave him some arable land in Walden, but as of Walden itself in 1354, when he gave Simon part of a Chipping Walden property near the Poultry (evidently part of the market, a century later Poultry Hill). Analysis of Walden tax-payers of the 1327 subsidy points to immigration primarily from within a 15-mile radius, which might suggest men who had already been frequenting Walden's market or doing business with locals; of eighteen offending butchers identified at a leet court session of 1387, only four were Walden men, the remainder from the surrounding region [Allan. op.cit., pp.57, 63]. Bassett speculated [p.26] that subdivision of the large blocks may have been individualized according to the intent of the lessee of each of the blocks; however, it might have been that blocks were progressively sub-divided, based on demand for tenements. Gold Street, which also connected to King Street, appears to have been created as the back lane to the tenements fronting the extension of the High Street south of Church Street. If by this time any settlement still remained in the area of the old Saxon village, the great ditch dealt it a further blow by cutting through one side of it, a possible further encouragement to some of the residents to move into the newly opened-up area.

This new town development – again, if we may consider it so – was less successful than the founder hoped. Any initial incentives to attract new settlers to Chepyng Walden may not have proven sufficient, or sustainable, (as alternative market settlements appeared in the region) to fill the space provided. Some of the chequers do not appear to have been densely settled, particularly those south of the new marketplace and in the eastern sector of the enclosure, excavations in the latter area not having produced the amounts of medieval pottery that would point to human occupation. Parts of the enclosed area reverted to agricultural or pastoral use. Surviving building fabric from the fourteenth to sixteenth centuries is largely in the northern part of the great ditch enclosure, around Castle and Church Streets, the High Street and its northern continuation (Bridge Street), and on Gold Street. Two-storey houses are documented on the High Street by the early fifteenth century, while one fifteenth-century building on King Street was a hall-house incorporating shops and may have been a merchant's residence; a few other late medieval or early Tudor buildings have front rooms facing out onto the street, some in corner positions and these rooms probably served as shops or workshops. By contrast, several examples of the more humble Wealden houses of fifteenth century date also survive in the town centre. A similar failure to meet expectations is also documented at Eynsham and to an extent at Winchelsea, as well perhaps at Bushey. The inquisition post mortem on earl Humphrey VI de Bohun in 1299 assessed the value of Walden's market and fair as an unimpressive £4 – comparable to the assessed value of Thaxted's market in 1295 – and mentions 57 burgesses there, not a huge number, while the lay subsidy records for 1327 list 65 taxpayers at Walden. Possibly the liberties conceded by the Bohuns to Chepyng Walden were not generous enough to have widespread appeal; the manorial court remained the principal institution for administering legal jurisdiction, under the presidency of the lord's steward, usually a non-local man, assisted by residents in minor offices typical of manors (such as capital pledges, ale-tasters, and bread-weighers), thus providing for only limited local influence over Walden affairs.

A royal investigation in 1392 of seigneurial rights in Walden, then held by the king, highlighted the lack of borough liberties by documenting a number of minor dues imposed on commerce and industry: a farthing for every quarter of malt bought, sold, or brewed for sale, the same from anyone who retailed on market days via a shop window or otherwise on his own property, and all bakers and brewers required to have their grain ground (for a price) at the king's mill; it was claimed (in a petition from Trinity Gild to the Crown) that, as a result, retailers were leaving the town and bringing life back to Newport's market. Switching base of operations was not new, however, for an Essex fine of 1293 shows a Matthew de Waledon, merchant, and his wife acquiring a messuage in Newport. By 1425 business at Walden's market had dropped off sufficiently that the burgesses declined to elect a market bailiff, for no-one was prepared to remain in Walden to serve, since the revenues from the market were insufficient to pay the lord's farm; resort was had to farming out the market revenues independently. Around the same period we hear of not only some tenements but also the manor-house being dilapidated.

Though there are indications of the crystallization in the fourteenth century of a more respected and more influential group within the community, not until the sixteenth would Saffron Walden gain the degree of self-government that came with incorporation (1549). This was foreshadowed a generation earlier when six prominent locals – including the vicar and his sister, Jane Bradbury, who had married a mercer and one-time mayor (1509) of London, and would be instrumental in setting up (ca. 1521) a grammar school at Walden (although schoolmasters, operating under abbey oversight, are evidenced in deeds of the 1320s to '40s and in 1402 and 1436, and a grammar school in 1511) – had organized as the socio-religious gild of Holy Trinity. In March 1514, after the king had rebuffed a petition by the these individuals seeking to buy out the market tolls and other royal rights in the manor, the gild received a royal charter giving it the power to meet corporately and make ordinances, and granting it a fair on the festival of Saint Ursula in late October, though the fair came to be held in early November – Dr. Allan [op. cit. p. 131] speculates that it was intended to compete with Newport's November fair. A couple of months later the gild obtained a royal grant of the Saturday market, a Lent fair on the Common (just east of central Walden), and the legal jurisdiction of Clerk of the Market, as well as the lord's grain mill and malt mill, all in return for an annual farm of £10 in lieu of market tolls and seigneurial dues such as mentioned above.

This arrangement highlights the fact that Walden was not yet formally a borough, something that would come in 1548 through the creation of corporate self-government to which the privileges of the gild, now dissolved, were transferred. The terms of the arrangement rather suggest that Walden had not been granted any charter of borough liberties whose text has not survived to us. Yet even before 1514 Walden could be referred to as a borough [e.g. ERO D/B 2/2/18, 2/1/233, 2/1/245-246, deeds of 1444, 1488, and 1505], though whether actuality or wishful thinking is not clear, for this descriptor is only rarely found, and in some cases may be the result of copying of terminology, so we should not give too much weight to this evidence. Yet regulations for Walden almshouses in 1400 refer to a 'clerk of the burgage' – though the role of such an official (suggesting some form of communal organization), and whether burgage here refers to a geographical area or the burgesses collectively, is not clear. Furthermore, the manorial court rolls refer to offences committed infra burgum, and on the whole support the notion that, locally at least, part of Walden had come to be perceived as a borough. Perhaps even the castle-town could be so perceived, for in 1355 we encounter a Walden resident with the surname Holdeborw ('old borough'?) [ERO D/B 2/4/9], possibly preserved a century later as the local surname Aldebury. Additional evidence supporting the perception that at least some residents of the new town held by burgage tenure comes from references to burgesses: one in the Bohun charter of 1300, and another in 1299, reported by Beresford ["English medieval boroughs: a hand-list: revisions, 1973–81", Urban History Yearbook, vol. 8 (1982), p.62]. Furthermore, Britnell identified 17 landless messuage transactions there, most being specified as in Chepyng Walden; as at other small towns, burgage plots may often have been transferred through manorial protocols and these transfers registered in documents that have not survived to us.

We should think in terms of one or more burghal components existing within medieval Walden – the Bohun charter of 1300 being targeted at a subset of Walden's population – rather than the vill in its entirety having been accorded borough status. Walden churchwardens' accounts for 1438-40 seem to indicate that, by then, the town was perceived as comprising the area within the great ditch (i.e. Castle Street, Church Street, the various stretches of the High Street, Gold Street and the marketplace neighbourhood), as opposed to the abbey manor of Walden St. Mary, to the west), the hamlets of Little Walden (north) and Siward's End (east), and various sub-manors that had arisen to the north.

Reduced seigneurial presence at Walden, after the castle was slighted, may have contributed to Walden's decline, while the market grant to the abbey and the gradual revival of the Newport market during the late twelfth and early thirteenth centuries cannot have helped matters; the old main road alongside the Cam, which had passed by the abbey, had probably by now regained some of the use lost when the Mandevilles tried to redirect traffic towards Walden. Nonetheless, growth in size and sophistication of Walden's community is suggested by the fact that three socio-religious gilds in Walden (none known to be connected with any particular trade), responded to the 1389 national survey of chantries, and a fourth is known by 1400; such associations are thought to reflect the coalescence of wealthier, more influential, more respectable, yet more ambitious elements of a community, while providing some experience of group consensus-forming and decision-making. That of Holy Trinity was the most significant, possibly using a guildhall known to have stood at one corner of the marketplace, next to which a new communal moot-hall was built in the early sixteenth century. The gild of Our Lady of Pity – perhaps a precursor to Holy Trinity gild in terms of serving as a vehicle for prominent members of the community to exercise influence [Allan, op.cit., p.227] – sponsored in 1400 the foundation and subsequent management of a group of almshouses, whose warden was, in 1435, appointed by the community of Walden. That local commerce remained active enough is evidenced by records of the manorial leet court, which dealt with market offences such as forestalling and regrating, charging excessive profits, and selling substandard goods [for some pertinent extracts from the rolls see Richard Braybrooke, The History of Audley End ... Notices of the Town and Parish of Saffron Walden, London, 1886, pp. 174-76]

Despite the failure of the planned extension to the original castle-town, and the increasing dilapidation of the castle, Walden's market not only survived but, in the fifteenth century, revived. We know that either the market or the fair was attracting custom from as far afield as Ely, for in 1234 the Bishop of Ely complained about toll being demanded at Walden from his men, contrary to their liberties. In the national taxation of 1334 Walden's assessed wealth was one of the lowest in the region – slightly exceeding that of Chelmsford and Newport, for example, but well below that of Cambridge or Colchester of course, and noticeably less than that of Maldon, Thaxted, or Writtle. The taxation of 1524/25 (on moveables rather than real estate and thus fairly reflective of the commercial/industrial sector) shows Walden, in terms of assessed wealth, in a middling to low position, among other small market towns of Essex and England: a little below Maldon and Barking, but slightly higher than Thaxted and Chelmsford. In terms of the size of the tax-paying population, at 380 it exceeded Barking (256) and Maldon (193) and, although a good deal smaller than Colchester (701 taxpayers), it was relatively large and prosperous compared to most Essex towns, and had shown strong improvement in its relative position over the period 1334-1524, in contrast to, say, only a small change at Colchester and slight decline at Cambridge.

This increase in prosperity was thanks in part to the large number of wool-producing sheep pastured in the area. This may not have been a major part of the business of Walden's market, for the region's wool was of inferior quality, and that from large flocks (such as the abbey's) may have been committed on contract to woolmongers; however, late fifteenth century court records give us the example of dyer John Reymond, who was more than once accused of using his private set of scales to weigh wool. Prosperity was also partly (perhaps particularly) due to the cultivation of the saffron crocus, from which was sourced a valued and costly spice, medicament, and a yellow dye for wool and for hair. Walden was the principal centre in England where saffron was cultivated, thanks in part to its chalky soil and suitable climate, though its cultivation was widespread in the region (Sawbidgeworth being another market town to benefit from that crop in the Late Middle Ages); though the first documentary reference to it at Walden is not until 1444, the 1327 subsidy shows the surname Crok there, which could point to a croker, grower of the saffron crocus [Allan, op.cit., p.58]. Walden's proximity to London provided a large demand centre, with specialized requirements, and a port for export to the continent, so it is not surprising that Londoners became active in marketing Walden's saffron, though quite a few residents shared in the profits by growing and harvesting crocus crops in their gardens or on small plots of land they rented for the purpose. A number of London mercers (who dealt not only in cloth but a variety of commodities) were involved with Walden residents, and some were holding fields there, in the fifteenth century and even the late fourteenth. The fair held in Walden on St. Ursula's Day coincided with the saffron harvest. The local importance of this industry led to Chepyng Walden becoming known (from the reign of Henry VIII) as Saffron Walden. Local availability of saffron dye is likely to have given additional stimulus to cloth finishing in Walden. Dyeing was certainly one of the town's industries, there being dye-vats installed, by the late fourteenth century, in the inner bailey's wet ditch, while in 1438/39 the aforementioned John Reymond was paying 2d. rent for a small plot on the manor's periphery, where he had a dyehouse. Part of Bury Hill was known as Teinters (i.e. dyers) Hill.

Walden's prosperity is also indicated by the fifteenth-century rebuild of the parish church, on a more impressive scale, as well as by a number of masonry foundations, for timber-framed structures, and cellars (cut into the chalk, some lined with flint) encountered by archaeologists and building contractors – again, in this regard, we are reminded of New Winchelsea. A number of the houses still standing in Saffron Walden today were built in the late fifteenth century, and by that time the market neighbourhood seems to have been quite densely built-up. The oldest surviving manorial court rolls show that even the earls had a town-house in Walden, though its location is unknown; the court for the Honour of the earldom in Essex was, however (at least during the time of Humphrey VIII), at High Easter, close to Pleshey. The prosperity and population growth suggested by Walden's ranking in 1524 had followed a period of depression around the mid-fifteenth century [Allan, op.cit., p.272-73] and there would be another decline following the Tudor period, as the saffron dye lost popularity and cheaper sources were exploited, and as the manufacture of woollen cloth became focused elsewhere. As in many other Essex market centres, the influence of London was increasingly felt during the Late Middle Ages and post-medieval period. Population growth was handled through sub-division of plots and filling in of open areas, so that there was little expansion of the medieval town layout or limits.

Using deeds as the main source of evidence, the same degree of occupational diversity noted above for 1400 is still seen later in the fifteenth century, although – as was common with smaller market towns – most industry was dependent on rural products of agricultural and pastoral activities. The cloth trade in particular is evidenced by men in various branches of the industry: fullers, tailors, drapers, mercers. A Fullers Lane (probably the present Freshwell Street, on the north-western outskirts of Walden), whose tenements (mainly cottages) backed onto a water-course, is mentioned in numerous deeds from the time of Edward III onwards, while there is also some indication of fulling taking place in Brook Walden. On the other hand, residents engaging in the earlier phases of cloth-making – weaving and spinning – are much less in evidence and may not have represented a large occupational group. The cloth trade is also evidenced from occupations, or occupational surnames, of Walden taxpayers in 1327, but numbers are small; a tailor is seen as a Walden land-holder, perhaps through marriage, as far back as 1256. Allan [op.cit. p.148] feels that the modest size of the cloth industry, and lack of any dominant textile specialization, does not allow late medieval Walden to be thought of as a 'wool town'. The same could be said of Walden in the early post-Conquest centuries, although to an extent this is the consequence of lack of documentation.

Leather-working is an industry better evidenced in deeds, by a range of trades such as skinners, tanners, barkers, and saddlers. It was evidently a relatively large occupational group, though this is not unusual in a small town in a livestock-rearing region. We also hear of butchers, bakers, maltsters (malting becoming an industry even more prominent in post-medieval Walden, because of the demand from London brewers), fishmongers, fishermen, a cobbler, hosier, chandler, cooper, blacksmith, collar-makers, braziers, masons, glaziers, a thatcher, shermen, and a gelder who operated from premises in Castle Street. Evidence from local court records expands this range a little, adding innkeepers, other occupations related to the building trades, and wage-dependent labourers. The overall impression is that Walden's economy in the Late Middle Ages was well-diversified, for a community of its size, and arguably urban in character [Allan, op.cit., ch.3 and 4, presents a much more detailed analysis of the economy and occupational structure of fifteenth-century Walden].

There were numbers of small traders, from chapmen who were house-holders, down to the level of pedlars and hucksters who were not property-owners. However, with the possible exception of mercers, substantial merchants engaging in long-distance trade are little in evidence – which may mean that they are not conspicuous in records, rather than that they did not exist. A possible exception is John Garlond, of whom a couple (one sometimes qualified as 'senior') appear in national and local records during the reign of Henry VI, variously described as chapman, maltman, merchant, or saddler, but we have little information indicative of the scope of either's business activities, and neither made much mark in positions of local administrative responsibility – only the maltster serving a single term as capital pledge. At his death (ca.1452), the senior John left a modest sum of money (including a charitable bequest towards upkeep of the roads) and 100 qt. of grain, while his widow, Cristiana, having remarried, was in the 1460s pursuing debts of 6 marks and £40 as executrix of the merchant. One of the Johns had farmed the market tolls in 1438/39 – likely enough the merchant – and the name is associated with tenure of some arable, and that of the saddler with operations in Cordwainers Row, but no documentation connects either with a town residence; on the whole there is no impression that John Garlond in any way stood out within England's mercantile class.

Even the few mercers seen in Walden do not appear to have been imbalancedly prominent, socio-economically. Yet some of the houses in central Walden – of two-storeys and incorporating one or more shops – may be indicative of merchants' residences. Possibly the mercantile role was being played, at least during the fifteenth century, more by Londoners, whose growing involvement with Walden's community was reinforced through propertied interests (as early as 1368) – particularly in the vicinities of the market and Fullers Lane [Allan, op.cit., p.104] – and perhaps through membership in a local gild. At the same time, some Walden traders who prospered may have moved on to the richer climes of London – such as a later member of Walden's Chapman family, who by 1495 had taken up citizenship and was operating as a mercer, and maybe also butcher Warin de Waldene who, in 1320, was sentenced by a London court to have the putrid meat he had put up for sale burned under his nose while he stood in the pillory – or conceivably to Colchester (although only Little Walden men are recorded as burgess entrants there). Fewer Cambridge businessmen are seen as engaging with Walden men, but the former must have played some role in the economic activities of the latter; for example, the needs of the university town may explain the high number of glaziers seen at Walden, and some building trades specialists who took work in Walden are also known to have worked on Cambridge projects.

Though medieval Walden may never have been conceded formal borough status through a seigneurial charter – assuming we are not ignorant of one of which no vestige has survived – various fragments of documentary evidence, combined with topographical, social, economic, and institutional characteristics possessed by the Late Middle Ages, suggest fairly convincingly that Walden was effectively urban, and was so perceived by at least a number of its residents. When incorporation and a formal structure of self-government was finally conceded to Walden in 1549, a communal seal became requisite; significantly, the imagery used on that seal depicted a saffron crocus enclosed within an iconic town wall.