Caerleon is of archaeological importance, being the site of a notable Roman legionary fortress, Isca Augusta, and an Iron Age hillfort.

By the Iron Age, the area was home to the powerful Silures tribe and appears to have been the centre of a wealthy trading network, both manufacturing and importing La Tène style goods.

[6] From the 5th century BC, the town was the location of a great Iron Age hillfort crowning a hill overlooking the River Usk and what would become the Roman port.

The hillfort at Lodge Wood Camp is defended by three lines of massive ramparts and ditches, and is the largest fortified enclosure in South Wales.

The name Caerleon may derive from the Welsh for "fortress of the legion"; around 800 AD it was referred to as Cair Legeion guar Uisc.

When discussing the disastrous flooding of Cantre'r Gwaelod in the time of Ambrosius Aurelianus, the author of the Triads of the Island of Britain notes that Medieval Caerleon is an exceptional city, "superior to all the towns and fortifications in Cambria".

[16] A Norman-style motte and bailey castle was built outside the eastern corner of the old Roman fort, possibly by the Welsh Lord of Caerleon, Caradog ap Gruffydd.

The Domesday Book of 1086 recorded that a small colony of eight carucates of land (about 1.5 square miles) in the jurisdiction of Caerleon, seemingly just within the Welsh Lordship of Gwynllwg, was held by Turstin FitzRolf, standard bearer to William the Conqueror at Hastings, subject to William d'Ecouis, a magnate of unknown antecedents with lands in Hereford, Norfolk and other counties.

At about the same time, Wynebald's lands may have passed via his daughter to Henry Newmarch,[19][full citation needed] possible illegitimate son of Bernard de Newmarch,[20] c. 1155 the Welsh Lord of Caerleon, Morgan ab Owain, grandson of King Caradog ap Gruffudd, was recognized by Henry II.

The wharf was located on the right bank, to the west of today's river bridge which marked the limit of navigability for masted ships.

A tinplate works and mills were established on the outskirts of the town, in Ponthir, around this time, and Caerleon expanded to become almost joined to Newport.

In book three of his Historia Regum Britanniæ, Geoffrey of Monmouth gives the founder of the city as Belinus, the mythical King of the Britons.

Geoffrey also states that Belinus' son and heir, Gurguit Barbtruc was buried in Caerleon, which he fortified with walls and ornamented with new buildings.

[28] Caerleon is also associated the legends around Dubricius and Saint David, and was commonly believed to be one of the earliest Metropolitan Sees in the Province of Britannia.

But on the other side, protected by meadow and woods, it was remarkable for royal palaces, so that it imitated Rome in the golden roofs of its buildings ...

[37] The historic remains of the Roman Legionary Fortress Isca Augusta is popular with tourists and school parties and there is a marked heritage trail in the town.

Ffwrrwm Arts and Crafts Centre is a small specialist shopping courtyard with a gallery restaurant and an eclectic display of sculpture.

In the north-west part of the town, across the railway bridges, the land rises sharply up to Lodge Wood and its hill fort.

[46] In August 2016, the Welsh Government announced that they would recommend that the main building, gatehouses and gate piers be listed as 'buildings of special architectural and historic interest'.

The University of South Wales expressed their continued opposition to the proposed listing but the announcement was welcomed by local politicians and the Caerleon Civic Society.

[47] Grade II listing of the Main Building, the Principal's Residence, Gate Piers and Caretaker's / Gardener's Lodge was confirmed on the 3 March 2017.

[51] Instead, the Tour de Gwent will be the main cycling event for South Wales each year, with a 93 mile route and other distances for different ability levels on offer.

It has welcomed international riders including Julian Alaphilippe, André Greipel, Tony Martin, and Geraint Thomas to the popular cycle routes in the area.

On 10 September 2017 the Tour of Britain came to Caerleon along the 180.2 km (112 mi) western route from Worcester to the competition's finish in Cardiff city centre.

The peak of the British domestic cycling calendar, it saw a dramatic breakaway over Belmont Hill by riders Gorka Izagirre (Movistar) and Mark Stewart (An Post-Chain Reaction) which is a Category 2 climb and has been a feature of the Tour with a 9% average gradient.

The event organisers sent riders from Newport city centre to Caerleon via Sustrans National Cycle Route 88, which was mostly flat along the Usk riverside.

The King of the Mountains stage was again set at nearby Belmont Hill, with Tour de France winner Thomas famously describing the climb as 'too steep'[53] after he lost lead position in the peloton to climber Alaphilippe.

The local ward golf club was included in promotional material for the 2010 Ryder Cup which was hosted at the nearby Celtic Manor Resort.

Bulmore Lido was opened in Caerleon in July 1934 land with an open-air swimming pool, cafe and restaurant,[56] closing in the 1980s.

Another of Hando's informants provides a description, dated 1841, of the Yuletide tradition: The custom of chaunting at their neighbours' doors on the Twelfth Night ... on which occasion they are fantastically dressed with ribbons of various colours.