Watling Street is the name given to an ancient trackway in England and Wales that was first used by the Celts mainly between the modern cities of Canterbury and St Albans. The Romans later paved the route, part of which is identified on the Antonine Itinerary as Iter III: "Item a Londinio ad portum Dubris" - from London to the port of Dover. The name derives from the Anglo-Saxon Wæcelinga Stræt, which has come to be understood as the A2 road from Dover to London, and then the A5 road from London to Wroxeter. Originally the word "street" simply meant a paved road (Latin: "via strata"), and did not have the modern association with populated areas.
The main section of the road is that from Dover to Wroxeter. It was named Wæcelinga Stræt by the Anglo-Saxons, literally "the street of the people of Wæcel". Wæcel could possibly be a variation of the Anglo-Saxon word for 'foreigner' which was applied to the Celtic people inhabiting what is now Wales. This source also gave us the name for Wæclingacaester (the Anglo-Saxon name for Verulamium) and it seems likely that the road-name was originally applied first to the section between that town and London before being applied to the entire road.
Like most of the Roman road network, the Roman paving fell into disrepair when the Romans left Britain, although the route continued to be used for centuries afterwards. It is likely that Chaucer's pilgrims used Watling Street to travel from Southwark to Canterbury in his Canterbury Tales.
This was the first Turnpike Trust and showed how financially hazardous the undertaking could be.
The Fornhill to Stony Stratford case provides more evidence that Parliament would void undertakers’ rights if they were negligent. The trustees for the Fornhill to Stony Stratford road borrowed more than 7000 pounds in 1707 and 1708 to improve the road. The creditors, however, claim to have been misinformed regarding the expected revenues from the tolls, and requested in 1709 that a new act extend the term and increase the tolls. A new act was passed in 1709 extending the term, but the tolls were not increased. It also included a provision that the creditors could take receivership of the tolls if the trustees had not repaid their debts by 1711.
Apparently, the trustees were unable to borrow and the creditors took over the tolls. In 1716, Parliament tried to clarify the situation by passing an act that vested authority in the trustees from the 1709 act and another group appointed by the Justices of the Peace for Buckinghamshire.
The 1716 act was not amended for its entire term of 23 years, but once it was set to expire, Parliament decided that it would not renew the rights of the existing trustees for the Fornhill to Stony Stratford road. In 1736, the trustees submitted a petition for an extension of their rights, but it failed to pass and in 1739 their authority ended. In 1740, a new act was passed naming a replacement body of trustees. In the petition for the new bill, the inhabitants of Buckinghamshire described the road as being ‘ruined.’ This sentiment was affirmed by the Member heading the committee for the bill.
The road was re-paved in the early 19th century by Thomas Telford who brought it back into use as a turnpike road for use by mail coaches bringing mail to and from Ireland, his road being extended to the port of Holyhead on the Isle of Anglesey in Wales. At this time the section south of London became known as the Great Dover Road. The toll system ended in 1875.
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 Shrewsbury is today known as the A5 (which now continues to Holyhead). At Blackheath the Roman road's exact path is uncertain: either diverting towards Deptford Bridge like the modern A2, or staying on a straight line through Greenwich to cross the mouth of Deptford Creek. Through Milton Keynes, the A5 is diverted onto a new dual-carriageway and Watling Street forms part of the new town's grid system and carries the additional designation V4. The name of the town of Wellington, Shropshire, which lies just east of Shrewsbury, is believed to be a corruption of the word 'Watling town' as Watling Street supposedly ran straight through the centre of Wellington.
The Roman Road from Catterick (Cataractonium) to Corbridge (Corstopitum) and onto the Antonine Wall also came to be known as Watling Street, with perhaps a similar Anglo-Saxon etymology owing to its path into the foreign land of Scotland. This route is also known as Dere Street. This may also be the case for another Watling Street between Manchester (Mamucium) and Ribchester (Bremetennacum) which ultimately led to another 'foreign land' in Saxon times, that of Cumbria.