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There is considerable evidence for prehistoric activity within the urban area, dating from the Mesolithic period onwards.  A crop-mark of a large circular feature within  the Roman fort area is thought to be that of a Bronze Age barrow.  There was a substantial Late Iron Age settlement on the site of the later Roman town, with a  shrine located approximately a kilometre away to the north-east.   However,  no evidence has yet been found to suggest that this settlement was urban in nature.

A Roman fort was constructed at Great Chesterford immediately to the north of the existing settlement in the first century AD, possibly as a consequence of the Boudiccan revolt in AD 60.  The existing  settlement continued, expanding at the end of the first century into the area of the abandoned fort.  This settlement developed during the second century into urban status, went through a period of decline during the third century before expanding again in the fourth century, culminating in the building of the town walls, making it one of only two walled towns in Essex, the other being Colchester.  Outside the walls there were extra-mural cemeteries, ribbon development (some of it industrial in nature) along the main roads and a Romano-British temple on the site of the Late Iron Age shrine.

There is sufficient evidence to deduce a large settled Saxon population at Great Chesterford from the end of the Roman period until at least the seventh century.  However, the evidence largely derives from burials and the location of the settlement itself is uncertain, although it has been suggested that it was the settlent site uncovered at Hinxton Hall, Cambridgeshire (T.E. Miller, pers. comm.). In the later Saxon period the settlement was probably on the same site as the later  medieval town.  There is no evidence that the Saxon settlements were urban in nature.

Following the Norman Conquest Great Chesterford became a royal manor, with its occupants holding right of copyhold.  The settlement was reasonably prosperous during the medieval period, largely due to the cloth trade. Archaeologically it is of interest as an example of an Essex settlement (apparently more of a village than a town in nature) that has developed according to the Midlands tradition, both in morphology and in  building-types.   Great Chesterford  is one of the few areas of Essex that retained its strip-fields until the enclosure acts of 1804.  The layout of the tofts within the town and on the outskirts are also Midlands in  style, with the main dwelling set back from the road.

The post-medieval period was a period of decline for Great Chesterford, mainly because of the collapse of the cloth trade.   However there was some trade from passing traffic due to the road link with Newmarket and Cambridge and the London-Cambridge railway.   Great Chesterford is now largely a commuter village for Cambridge.