The earliest recording of a Henley bridge is in the Patent Rolls of 1232. Leland, who died in 1552 mentions it in his ‘itinerary’ stating that it was composed entire of wood. It is also known that as far back as as 1514 a chapel, dedicated to St Anne, existed on the bridge itself. In 1642 the bridge was partially destroyed, either by the Royalists or Parliamentary forces, during the fighting of the district and was not repaired until 1670. In 1754 it was declared dangerous and before any work to repair it was done, a great flood in 1774 swept it away.
The present bridge was built in 1786 to the design of William Hayward of Shrewsbury at a cost £10,000. Unfortunately he died before it was completed and his body is buried in the chancel of St Mary’s Church. It was built by Oxford mason, John Townesend. A toll bar was placed on the Berkshire side of the river and it took a 100 years for the cost of the bridge to be paid off and the toll was then removed.
However when the Carpenter’s Arms pub was demolished in 1984 an arch of an earlier bridge dated to be circa 1170 was found where site of the Henley Royal Regatta HQ is now.
The keystones on the bridge were carved by the Hon. Mrs Damer and represent Tamesis (ancient name of the River Thames) and Isis. Mrs Damer was very well-known in the artistic world of her time and Horace Walpole was a great admirer of her work. She was a frequent visitor to Park Place during General Conway’s ownership. Horace Walpole bequeathed her his Strawberry Hill property and she lived there to a great age, dying in 1828.