Before 1410 travellers crossed the Thames at Chertsey by ferry at a point close to the current crossing. In that year King Henry IV granted a license for the building of a bridge which was to be maintained by the Abbot of Chertsey Abbey.
The first Chertsey Bridge was made of wood and was 210 feet long and 15 feet wide. It stood slightly downstream of the present bridge, and suffered much damage from the ravages of the Thames flowing beneath it, and the frequent collision of barges in to it.
By the 17th century the bridge needed to be rebuilt, and further repairs were needed in 1681. Repairs took place regularly until 1779 when the bridge once again was in need of being completely rebuilt. The bridge committee met to find a solution to the problem, and it was discovered that the ait projecting from the Surrey side was causing the currents of the river to flow against the abutments of the bridge, weakening the structure. Architect James Paine of Sayes Court, Addlestone, was given the job of investigating the costs of such an undertaking. His recommendation was not only to remove the part of the ait, but that the wooden bridge should be replaced with a 5 span stone one at a cost of £7,325.
Paines proposal was accepted, and Charles Brown, a carpenter from Richmond, accepted the tender for the work. On 26th June 1782 the Duke of Northumberland and Lord Onslow laid the keystone for the new bridge.
The new bridge immediately ran in to difficulties. Working from the keystone outwards, the 5 span bridge was gradually built, but it soon became clear that, possibly due to an oversight by Paine, the bridge did not reach across the river and a further arch had to be constructed on either side at a further cost of £2,800.
The new bridge was finally finished in 1785, and the old bridge, sold to James Paine for £120, was dismantled.