The hundred of Ongar was focused on the Roding valley, a north-south passage connecting London with Suffolk, long one of the principal drovers' routes in East Anglia. Chipping Ongar grew up, in a central position in its hundred, within an angle formed by the Roding river barely deserving of the name at this point (unlike at Barking), although still needing bridging and a tributary, the Cripsey Brook. In 2004 archaeologists discovered a large Roman road that led from London to Chipping Ongar before turning north towards the small Roman town at Great Dunmow, whence there was a road to Colchester; but if this meant that Ongar was itself the location of any sizable Roman settlement, archaeology has not yet demonstrated it convincingly. Similarly, indications of a rectangular earthwork enclosure immediately south of the medieval town have yet to confirm the hypothesis it represents Saxon settlement.
In Domesday Chipping Ongar is recorded as one of two manors named Angra, which are not distinguished by prefixes; the other became known as High (or Great) Ongar, out of whose parish the site of Chipping Ongar was carved, and so the latter was referred to as Little Ongar, as well as Ongar at the Castle (as late as 1450). When it acquired the Chipping prefix, and the market function to which the prefix alludes, is uncertain, but the first surviving reference dates to1308 and its use began to prevail as the century progressed. We cannot safely argue for a Saxon market on the grounds of the prefix. Yet there is speculation the place served, prior to the Conquest, as the main market of the hundred, for it was where the hundred's folkmoot met; if so, the market would have had no known competition in the hundred before the reign of Henry III, when the lord of the manor of Theydon Mount, a few miles south-west of Chipping Ongar, obtained a licence for market and fair (1225). The soil of Ongar a Saxon term for grassland, suggesting it had long been used for grazing or cultivation was good for growing grain and pasturing sheep. The Domesday entry records 112 sheep, far outnumbering the number of cattle and of swine, even though the surrounding woodland would have provided, it was estimated, forage for a thousand pigs; the heavy forest limited the amount of land brought under cultivation. The human population at that time was quite small.
Eustace II, Count of Boulogne the greatest lay holder of Essex real estate at the time of Domesday, held the lesser Ongar in 1086, along with the hundred, and it may have been he who put up the motte-and-bailey castle, perhaps on the site of the Anglo-Saxon folkmoot; alternatively the castle might have been raised by his like-named son and successor (from 1087), in the context of his participation in the rebellion against William II in 1088. The settlement at Ongar thereafter served not only as the principal place of the hundred but possibly as the English caput of the collection of estates known as the Honour of Boulogne, though Witham could also lay claim to that role, and, besides, the main focus of the Honour was in France. Eustace III was not much in England, being involved in the First Crusade. Through marriage to Eustace III's daughter, the honour came to Stephen, subsequently king. By 1157 the castle was in the hands of Richard de Lucy, who had married into the Boulogne family; so too was the hundred and the manor of Chipping Ongar (the latter kept as demesne land after other sub-manors had been granted within the hundred); the two continued to be linked as the estate descended to the Rivers family and then the earls of Stafford. A Rivers lord claimed that the manor had come to the de Lucy by gift of Henry II, although this may have been a diplomatic statement, as it in fact seems to have been granted to Richard ca.1153/54 by King Stephen's son, who was then Count of Boulogne.
Certainly Richard de Lucy (ca.1089-1179) was held in high regard by Henry II who, upon taking the throne in 1154, appointed him Chief Justiciar of England, a post he held jointly with the Earl of Leicester until 1158, whereafter he held it alone. He also served a term as sheriff of Essex in 1156/57. He had served King Stephen well, did the same to his successor, and this helped him build up a collection of properties, mostly in Essex, to the extent that they could be referred to as the Honour of Ongar, possibly with Little Ongar as its caput, though it was an artificial creation not passed along wholesale to descendants [J.H. Round, "The Honour of Ongar", Transactions of the Essex Archaeological Society n.s. vol.7 (1898), p.142-53]. Richard retired into an abbey in 1178, just a few months before his death. His brother Walter was Abbot of Battle (1139-71) and thus lord of the new town that had been established alongside it; Walter fought for independence for the abbey from episcopal oversight, with some assistance from Richard. Richard's younger son, Godfrey, became Bishop of Winchester (1189-1204) in which role he founded a market town at Alresford about 1200, in 1202 acquired a fair licence for Witney (Oxon.), where there was probably already a market in operation, and either he or his successor went on to promote the villagers to burgesses, probably laying out a new town there too. The first documentary reference to the castle at Chipping Ongar (1157) is associated with Richard's tenure. Whether Richard himself had any role at fostering urban development at Chipping Ongar, however, is unknown, though he may have been responsible for substituting the stone keep atop the castle motte.
The line of male heirs being extinguished with Richard de Lucy's grandsons, a female heir, Maud de Lucy, brought Ongar to her second marriage, in 1214, to Richard de Rivers. It was their son, another Richard de Rivers, who in 1222, shortly after coming into his inheritance, obtained a provisional licence for a fair at Chipping Ongar; it was to be held around the July festival of St. Martin, the dedication of the parish church. The licence was provisional upon Henry III approving it once he had come of age, though since we have no further reference to a fair there until the nineteenth century (when an October event), we cannot be certain the approval was obtained, or necessarily sought. On the other hand, we have references to the market there in 1287, when John de Rivers' steward made out a bond to a London tailor in the amount of 8 quarters of corn of the highest quality sold in Chipping Ongar's market, and again in 1294 in the inquisition post mortem on John, which identifies a Tuesday market as an appurtenance of Ongar ad Castrum, but mentions no fair. His son, another John de Rivers, was more interested in his estates elsewhere in England; in the early fourteenth century he leased the manor first to a minor bureaucrat, then to the ambitious Despensers, while during the minority of his heir it came to the Earl of Gloucester (linked by marriage to the Despensers).
In this fashion the lordship of Chipping Ongar moved out of the Rivers orbit, so that by mid-century it was part of the Stafford earldom and thus continued to the close of the Middle Ages. Consequently in 1354 the market at Chipping Ongar is referred to as belonging to the Earl of Stafford; this in the context of toll fraudulently taken, by an impostor claiming to act in the name of the earl's bailiff there, from a farmer bringing a quarter of oats to the market to sell. Diminished seigneurial interest in Chipping Ongar may also be hinted at in the fact that, whereas we hear of both a water-mill and a windmill there in the thirteenth century, an extent of the manor in 1372 mentions only a ruinous windmill. The decline in importance of the castle likely contributed to commercial stagnation at Chipping Ongar, whose market was probably based on the sale of agricultural produce and livestock; there is no indication of any significant industry there, and Chipping Ongar was not known as one of the main Essex cloth-making centres.
The topography of Chipping Ongar suggests that a town was established in association with the castle. The motte was encircled by a wet ditch, to the west of which was a large bailey, while an eastern bailey is also evidenced, the former generally being described as an inner bailey, though with somewhat tenuous justification, and the latter an outer bailey. The former in its turn was enclosed on three sides by an embankment/ditch stretching further west, just beyond which the terrain dropped off towards the wide brook, running on a north-south course; the river lay a little east of the castle. The embankment enclosed the so-called manor-house, situated immediately south-west of the western bailey, the church of St. Martin a little south of the manor-house, and the entire settlement, which mainly lay on either side of a gently curving north-south street (later the High Street), exiting the embankment at each end. This street, widening after its narrow entry through the gateways, must have served as the marketplace. Cartographic evidence favours the interpretation of a layout of plots of the narrow-and-deep burgage type on either side of the street: on the east side terminating at the western bailey, but on the west side along a fairly straight rear boundary ditch, separated from the embankment by an open area, probably intended to facilitate defence, but subsequently used for dumping rubbish. It should be noted, however, that we have no explicit reference to burgages or burgesses in relation to medieval Chipping Ongar. Smaller plots around the manor-house and church may point to an older village, or could represent encroachment into part of a churchyard; although the manor-house is a late medieval structure, its site could conceivably have held an older building, superseded by the castle, but rebuilt once the castle fell into disuse and disrepair (demolition taking place in the sixteenth century). The castle's main entrance was through the western bailey defences, at the point closest to the High Street where the latter was at its widest; that is, castle access favoured the settlement and particularly its marketplace, rather than the river on the other side of the castle.
This was, in its broad strokes, a fairly typical castle-town layout and it seems probable the embankment around the settlement was part of the overall defensive plan, contemporary with the construction of the castle, assumed to have been in late eleventh or early twelfth century, or a slightly later addition to the castle. It is possible that both castle and town were founded by Richard de Lucy an interpretation endorsed by Petchey ["The archaeology of medieval Essex towns," in Archaeology in Essex to AD 1500, Council for British Archaeology Research Report no.34 (1980) p.116], though he immediately went on to give evidence to the contrary. But the morphology seems more like that of earlier Norman castle-towns. Pottery recovered from small excavations on the enclosure around the town is from eleventh to thirteenth centuries and so does not help in narrowing down the date of construction. The parish church, or at least its site, appears to have been an integral part of the overall plan, but that does not preclude the plan being one of expansion of the castle and planting of a town in the time of Richard de Lucy. On the basis of its oldest fabric, St. Martin's church is generally thought to have been built perhaps as early as 1070, or as late as the mid-twelfth century; yet it could have been preceded by an older structure serving the needs of the Domesday villagers, for it was not sited directly adjacent to the High Street, nor does its position point to origins as a castle chapel. Scientific analysis of some of the bricks used in the structure (often incorrectly assumed as reused Roman material) suggests a date of manufacture between 947 and 1134 and most probably pre-Conquest [Sophie Blain, Ceramic building materials in early medieval churches in north-western France and south-eastern England. PhD thesis, University of Durham, 2009, pp.283-84] though they do not correspond to other known types from Essex and may have been imported, or re-used from some other structure elsewhere; the same kind of bricks were used in the entranceway into the western bailey. The usual maintenance, along with some improvements, to the church took place in later centuries, but no great investment in rebuilding or expansion is evidenced during the Middle Ages, apart from addition of a fifteenth-century bell-tower; the advowson always remained with the manorial lord, never having been coveted by any other authority, for the living was a poor one; Chipping Ongar seldom features in royal records, and then mostly when the king had the presentation to the church during the minority of an heir to the lordship.
If the date of foundation of a postulated town at Chipping Ongar remains an open question, we can say with greater certainty that the form and extent of medieval Chipping Ongar did not alter much in the late medieval and post-medieval periods, with the exception of some expansion along the axial street beyond the town embankment which shows signs of having lost its purpose and value to residents by mid-fourteenth century; the expansion mostly took place at the southern end of the road, where it descended to a bridge across the Chipsey, before diverting towards London. Despite this meagre growth, fourteenth-century taxation evidence suggests a level of wealth and density of population to indicate that Chipping Ongar was surviving as a small market town, although we have very little information about its occupational structure. In the post-medieval period the town benefited as a stopover point for travellers between London and Suffolk, and this may have been the case in the Late Middle Ages. Market activity continued at a level sufficient to warrant construction of a market-house in or before the seventeenth century.