After the Romans left Britain planned road building ended. Some of the Roman routes fell into ruin, and tracks were maintained only by way of constant use. Bridges were destroyed to halt invaders, and long journeys became very difficult. The only travellers were pilgrims, starting with those who went to Canterbury following the murder of Thomas a Becket (1190). Road maintenance became the responsibility of local monasteries, or of hermits who built shelters on the roads and asked for alms to pay for the repairs they did.

Wagons could not pass on the roads, the conditions were so poor. Pak horses and mules were all that could make the journeys across country. In the reign of Elizabeth I an act was passed in 1555 providing for forced labour to repair roads into market towns.....but little came of it. Then from 1564 stage-wagons began to provide a service in the south, up to eight horses pulled the wagons at a speed of only three miles an hour. Stage coaches started a century later, the roads still no better. Farmers sowed and ploughed on roads adjoining their fields. In 1660 Ralph Thoresby reported the Great North Road was “difficult to trace....and lost completely in places between Doncaster and York”.

Stuart laws tried to improve things, by reducing traffic not by building roads. James I tried to make 4 wheel carts illegal, Charles I banned more than five horses per cart and stopped all Sunday travel. Then in 1663 the first Turnpike Act was passed, establishing the principle that those who use the roads should pay for them. The first three toll booths were erected on the Great North Road at Stilton, Caxton and Wadesmill.As the booths spread so did opposition, booths were regularly pulled down or burnt, and in 1728 it became a crime punishable by three months imprisonment to destroy a toll-booth.

Slowly the roads improved, but still on a local basis with little planning to link improved sections in neighbouring Turnpike districts. By 1815 new methods of road construction were intoroduced, and two Scotsmen were prominent in this: John MacAdam and Thomas Telford. In 1715 the boast of the Edinburgh - London stagecoach  was to ‘complete the whole journey in 13 days without any stoppages if God permits’, by 1830 the time taken was down to 40 hours.

But Holyhead is our destination, and although Watling St reached Wroxeter near Shrewsbury in Roman days, there was no direct route beyond that towards Ireland. The old coach road went up to and along the North Wales coast via Conway (as does the modern A55 Expressway). However, this road was in a dire state, as Macauley reported: “in 1685 a Viceroy going to Ireland was 5 hours in travelling 14 miles.... between Conwy and Beaumaris he was forced to walk.... his coach was with great difficulty and many hands brought after him entire. In general, carriages were taken to Conwy and carried by peasants....”. At the start of the 19th Century this road was under the control of 123 different Turnpike trusts, had poor drainage, and was crooked and steep. Yet from the 1800 Act of Union this was the road that Irish MPs had to use to get to Westminster. In 1808 the Postmaster general declared the road unsafe for a mail coach.

So in 1810 Thomas Telford was commissioned to survey the road from end to end and to rebuild it. He chose a new route through Wales, and when the road was opened in 1830 it was regarded as a model of ‘the most perfect roadmaking that has ever been attempted in any country’. It had cost £750,000 to build.

For most, but not all, of the way, Telford’s road follows the course of the Roman Watling Street. It leaves London at Islington, meeting up with Watling Street in St Albans.

When the Dept of Transport allocated road numbers in the early 20th Century, the road from London to Holyhead was classified as the A5. In England it follows the line of Watling Street more faithfully than Telford, but in Wales it is the road Telford built.