The parish of Epping, near the south-western edge of Essex, was adjacent to that of Waltham Holy Cross to the west. The earliest settlement (apart from an Iron Age hill-fort) comprised a small number of scattered farmsteads, served by a church, along a ridge bordered by the dense forest for which Epping is still best-known. It was Waltham Abbey that, from about the time of its re-foundation (1177) as a house of Augustinian canons and Henry II's grant of Epping and its church to the abbey, undertook the assarting of a heath and surrounding parts of the forest – furthered by an authorization from Richard I, perhaps partly retrospective – which opened up an area to the south of the original settlement, on the boundary of a third parish. The valley of a brook separated the two areas, subsequently known as Epping Upland and Epping Heath. The canons' intent was to make more land available for cultivation, but some settlement was attracted to Epping Heath, in the form of smallholdings focused on agriculture, there being little meadow or pasture to support livestock, except perhaps pigs, which could grub in the forest, while Domesday also evidences a modest number of sheep. By mid-fourteenth century, however, we are seeing moderately large areas of pastureland changing hands.

The early settlement on the heath developed, or was expanded, into a town, possibly at the time of the acquisition by the abbey, in 1253, of a licence for a market to be held on the heath every Monday; the same licence gave the right to hold a three-day fair at Easter, this early season suggesting it might possibly have been primarily for spring wool or new-born livestock (particularly lambs). Licences usually specified that markets be held on the grantee's manor; Epping Heath lay within the abbey's manor of Eppingbury, but why the licence explicitly identified the heath as the market site is unclear, unless it was to avoid any confusion with the abbey's long-existing market at nearby Waltham. A few miles north-east of Epping Heath lay Chipping Ongar, and four miles to the north the town of Harlow, both already possessed of markets. But with a London-Cambridge road running, probably via Waltham, through Epping, then via Harlow, the abbey evidently felt there was enough commerce to warrant a market additional to those already established in the area. The Epping Heath market settlement was situated where the through-road crossed a second ridge, connecting the Roding and Stort valleys. A rental of Eppingbury manor in 1235 shows that most of its population was settled on Epping Heath; some informal trade had likely developed before the market licence/fair was obtained.

That licence was part of a larger package of royal grants to the abbey that included franchises for several of its manors, including fairs at Waltham and view of frankpledge on all manors. Furthermore, the king sent a letter to Richard de Mountfichet, his keeper of the forest in Essex, ordering him to allow the abbot to erect stalls and shops there, and anything else necessary for operation of the market, using his own timber (presumably meaning from the royal forest); this has been taken to imply plantation of an urban component [M.R. 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; Maria Medlycott, Epping - Historic Towns Assessment Report, Essex County Council,1999, pp.3-4] although the author of the Victoria County History entry on Epping portrayed the town as an organic development. There is no medieval reference to burgages or burgesses at the site of what seems to have been known into the fourteenth century as Epping atte Hethe, or Eppingheth, and later became known as Epping Street, but the topography suggests planned creation of a market settlement. Part of the through-road, the later High Street, was evidently widened to serve as a cigar-shaped marketplace, and house plots laid out along only one side of the street, with the opposite side developed at a later time. The High Street extended as far as a green at its north-eastern end, conceivably useful as expansion space at fair-time. North-westwards from that green ran Lindsey Street. whose name is known from about 1200, towards Epping Upland; it could have been along this route that pre-1253 settlement concentrated. It is not clear that the entire stretch of the High Street was used for the market; the bulging section was more central and it was there, near where minor roads terminated at the High Street and next to a chapel – presumably constructed to serve the medieval residents (the parish church in Epping Upland being at some distance) – that a market-house was later erected, though whether this existed before the close of the Middle Ages is doubtful.

The VCH holds that the original market settlement was on the west side of the street, where the chapel was situated alongside the marketplace, but Petchey thought it the east side, and Medlycott echoed both hypotheses at different points in her report, without appreciating the contradiction; a more recent report [Epping Forest District Council. Epping Conservation Area Character Appraisal and Management Plan, 2] is completely at odds with earlier theories by stating (without giving supporting evidence) that the High Street and its marketplace were a post-medieval development, but this does not seem consonant with other evidence. Petchey's view is supported by the presence of a continuous back lane providing rear access to all the properties on that side, which seem to form a coherent unit of plots, with narrow street frontages but shorter than the normal burgage type, for they had to terminate at what was the forest's edge and parish boundary. Archaeological evidence (which is slight) suggests habitation of at least part of the west side of the street before the close of the thirteenth century, but the only remains of a medieval house were identified on the opposite side of the street. Epping town's origins are similar in some respects to the town foundation at Brentwood, except that the west side of Epping's High Street may not have been intensively built up until the post-medieval period.

The manorial court exercised leet jurisdiction, dealing with the assizes of bread and ale and market offences, and appointed a constable and ale-tasters each year, but few records of the medieval sessions have survived and have not yet been studied in depth, so we cannot gauge the character of commercial activity to the same extent as is possible for Earls Colne. There is no sign of any communal organization that would bolster the case for classifying Epping as urban during the Middle Ages. Very little archaeological investigation has taken place in the vicinity of the medieval marketplace that might help throw light on the question. Writers have generally accepted that Epping was a new town of the Middle Ages, but it remains possible that any plantation was not intended as a town, but simply a market settlement of cottage properties, and that an urban character developed only gradually. The hundredal enquiries of 1274 give us what may be a glimpse of growth of the planted settlement on Epping Heath, through the presentation by the jury of Waltham Hundred (granted by Richard I to the abbey) that the abbots had encroached on royal land at Epping (possibly meaning the forest), subsequently held by two dozen men and women, whose surnames suggest the presence of a miller, tanner, carpenter, wheelwright, smith, and brewer in the community, while one man had the surname Neweman, which might be indicative of an immigrant; but these names are hardly a clear portrayal of an urban society. In 1343 we find Robert Hubert, an Epping resident (though son of a Harlow man) acknowledging a debt of £10 to a Sienese merchant, subsequently repaid, but we have no further details, and we can hardly generalize from such slight evidence of commercial activity (if such it is).

Following the Dissolution – Waltham Abbey having resisted royal takeover until 1540 – the new lord of the manor obtained, in 1575, three years after being granted Epping manor, a licence to reactivate the market and fair, which were said not to have been operational for some time; the day of the market and date of the fair were altered by this new grant. Although the abbey was for a time the wealthiest in Essex, it had been experiencing some financial difficulties in the early fourteenth century – prompting the king to authorize (1342) it cutting down and selling timber from the royal forest at Epping – was hard-hit by the Black Death, then had been a target for the Peasants' Revolt, and in the early fifteenth century the serfs of some of its manors, including Epping, were refusing to perform customary services due the abbey. These problems may have contributed to the decline of Epping's market. Following post-medieval improvement of the through-road, Epping's fortunes revived for a while as a coaching stop on the route between London and various East Anglian towns.