The valley of the River Usk would have provided plentiful resources for prehistoric hunter-gatherers; their transitory passage left little lasting trace on the landscape. With the development of farming it is likely that the area was gradually settled, albeit sparsely.

By the Iron Age, a recognisable pattern of settlement had developed around Caerleon. Lodge Wood hillfort, overlooking Caerleon, was the largest of a group of defended sites clustered around the confluence of the Afon Lwyd and the River Usk. Smaller enclosures on surrounding hills, such as those at Pen-toppen-ash and Cae Cam, were probably family-held farmsteads. The inhabitants of these farms would, of necessity, have practised a mixed agricultural strategy of cultivation and animal husbandry. Limited archaeological evidence suggests that in the Iron Age the land below Lodge Wood hillfort was grassland with patches of scrub and small trees, probably used for grazing.

Caerleon lay within the territory of the Silures, a tribe whose conquest cost the Roman army much time and blood. Wales was not pacified until around AD 75; only then could the final disposition of the legionary garrisons be decided. York, Chester and Caerleon were chosen as the sites for the three permanent legionary fortresses of Roman Britain. Together with Chester, Caerleon was responsible for the military administration of the Welsh tribes.

As a permanent base, the site was selected with care; the fortress was built on the end of a low ridge stretching from Lodge Hill to the River Usk, on ground above the level of the surrounding floodplain. To the south and west the ridge was surrounded by a bend in the Usk, to the east by the Afon Lwyd, producing a site well provided with natural defences and free from flooding. Siting the fortress close to the mouth of a tidal river allowed supply by sea, vital if the fortress was to maintain a year's supply of food.

Caerleon was known to the Romans as Isca, named for the river beside which the fortress was built. Isca was garrisoned by the Second Augustan Legion; the soldiers of the legion not only built the fortress, but also the network of roads and auxiliary forts through which the newly-subdued tribes were controlled.

At its peak the fortress was a small town in itself, with a garrison of 5500 professional soldiers. Within the walls were barracks, a large baths complex, drill halls, workshops and granaries. Some of the main streets were lined with small shops selling food and drink, pottery and other goods to the soldiers, either run by the army or contracted civilians. Outside, a small town grew up with temples to Diana, Jupiter Dolichenus and Kithras and further baths, shops and houses. The amphitheatre, built just outside the fortress walls, was used by the army for training, as well as gladiatorial shows. Roads leading out of the fortress were lined with cemeteries, as burial was not permitted within the bounds of built-up areas.

Isca remained the base of the second Augustan Legion for over two centuries, although much of the garrison was posted elsewhere for long periods. The Second Legion fought in Scotland and built a share of Hadrian's Wall and the Antonine Wall, while detachments fought in the Empire's wars abroad. The fortress must have been partially abandoned at times, for dedication stones record the periodic reconstruction of buildings which had fallen down, probably due to neglect.

The army abandoned Isca toward towards the end of the third century AD, after dismantling or demolishing some of the major buildings. Many others remained standing and in use long after the departure of the army; the fortress remained inhabited following the end of Roman rule in the fifth century AD. The still-standing fortress baths were turned into cattle-pens and small structures were built among the ruins inside and outside the fortress walls.

In contrast to the squatter occupation suggested by archaeology, post-Roman Caerleon is linked in legend with King Arthur. The Mabinogion and Geoffrey of Monmouth, among others, site King Arthur's court at Caerleon, while the overgrown ruin of the amphitheatre became linked with the Round Table. Caerleon was also popular with medieval tourists, notably Gerald of Wales who wrote a vivid description of The Roman remains.

Julius and Aaron, two early Christians, were martyred at Caerleon, possibly in the early fourth century, a church dedicated to them stood across the river from Caerleon on Chepstow Hill. The dedication of Caerleon Church to the Celtic St. Cadoc suggests a pre-Norman date for its foundation, possibly as a Welsh clas, although this is uncertain.

Caerleon castle appears in the Domesday book, and was probably founded by Caradoc ap Gryffyd, Lord of Caerleon, or his son Owain. Castle and lordship remained in Welsh hands, with some interruptions, until the thirteenth century. The early castle would have been constructed of earth and timber, the impressive motte survives in The Mynde. A borough is first mentioned in 1171; as no charter survives it remains uncertain whether it was founded by the Welsh or Normans.

Castle and borough were seized in 1217 by William Marshal the Elder, and separated from the remainder of the Lordship, which remained in Welsh hands until taken in 1270 by Gilbert de Clare. After the castle fell into Norman control it was rebuilt in stone; it was probably at this time that the shell of the fortress baths, which had survived for more than a thousand years, was demolished for its building materials. The new castle extended as far as the riverside, a single tower still stands next to the Hanbury Arms.

Medieval Caerleon was largely sustained by its market and port; ships from Caerleon maintained a thriving trade across the Severn and reached as far as Portugal. Profits from trade paid for a market house on the High Street and for large town houses; two sixteenth century houses survive as the Hanbury Arms and the Bull Inn. The town remained small, occupying less than half of the area of the fortress. As a result, much of the below-ground Roman remains survive.

Until the end of the eighteenth century, the Usk was spanned by a timber bridge, sited just upstream of the current bridge and probably on the site of the Roman bridge. The decking of the bridge was loosely fixed to allow it to rise and fall with the tide, a feature which impressed visitors to Caerleon when they first encountered it. This bridge was in poor repair for much of the eighteenth century and was largely destroyed in a storm in 1779. The present stone bridge was built early in the nineteenth century, although its dedication slab may be from another bridge entirely.

Caerleon was largely bypassed by the Industrial Revolution, which was concentrated in the Valleys and these looked to Newport as an outlet for their products. Although a tin plate works was opened on the outskirts of the town in the mid-eighteenth century, linked by tram road to the river and the Monmouthshire Canal at Cwmbran, Newport had overtaken Caerleon in importance and rapidly stifled it. In due course Caerleon became a suburb of Newport.

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