Watling Street was a Roman road in Britain which went from Dover on the southeast coast of England. to the port town of Holyhead on the Irish Sea coast of Wales via London, Verulamium and the English Midlands.

The street was an important part of the road network that the Romans constructed during their occupation of Britain. See Roman Britain.

Like most of the Roman road network, Watling Street north of London fell into disrepair when the Romans left Britain. It was brought back into use in the early 19th century by Thomas Telford as a Tollpike road for use by mail coaches bringing mail to and from Ireland. It was likely that Chaucer's pilgrims used Watling Street in his Canterbury Tales.

Most of the road is still in use today apart from a few sections where it has been diverted. The stretch of the road between London and Dover is today known as the A2, and the stretch between London and Holyhead is today known as the A5, although some of the original route near London has become part of the M1 motorway. A Watling Street still exists in the City of London, close to Mansion House tube station, though this is unlikely to be on the route of the original Roman road. Nuneaton, Dartford, Gravesend, Rochester, Gillingham, Canterbury and St Albans have Watling Street still under its own name.

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