The Romans built a crossing some 1 kilometre (0.62 mi) upstream of the current bridge at Chepstow, and this is thought to have continued in use for centuries thereafter.

[1] After the Normans established a castle at Chepstow (then known as Striguil), a wooden bridge was constructed across the river at or close to its current site.

Rebuilding was made difficult by the tidal range, requiring ten 40-foot-high (12 m) timber piers, perhaps the highest in the country at the time.

[1] However, in 1785, the wooden piers on the Monmouthshire side were rebuilt as four stone arches, although the Gloucestershire half remained timber until 1815.

Rennie's designs, at an estimated cost of £41,890 (equivalent to £3,750,000 in 2023),[5] were considered to be too expensive, but action was eventually taken after a ship collided with the wooden bridge in 1812, demolishing part of it and causing six deaths.

[6] In 1814 the contract to build the bridge was let to the Bridgnorth firm of Hazeldine, Rastrick & Co., at a cost of £17,850, less than half that of Rennie's estimate.

[6] It is described by architectural historian John Newman as "a supremely elegant composition of five shallow segmental lattice arches carrying the gently curved roadway...

[a][10] Carrying the main road between Gloucester and South Wales, the bridge became a notorious bottleneck and was strengthened several times.

[12] The bicentenary celebrations included a re-enactment of the original opening ceremony, with speeches from local civic leaders and Sir John Armitt, the president of the Institution of Civil Engineers.