The shield depicts a bridge over the River Thames. The present bridge at Maidenhead was built in 1772-7, but the river has been bridged at this point for nearly seven centuries, and this link in the ancient highway between London and the west has been an important factor in the growth of the town.
The crest forms a rebus or heraldic pun on the name-form Maidenhead, which began to come into use in the seventeenth century. From 1612 till the grant of arms in 1947, Borough documents were sealed with the seal of a foreign ecclesiastic, one John Godayn, a canon of Thiers in Auvergne. This seal dates from pre-Reformation times and one likes to think that one of the Wardens of the Guild, out of which the Maidenhead Corporation was founded, was in some way connected with the collegiate church of Thiers. The seal consists, besides the legend round it, of a stylized priest's head. This head might easily be mistaken for a woman's and in later reproduction, notably in the jewel attached to the Mayor's Chain, it certainly became feminized. And so a maiden's head is now the officially recognised Crest of the Borough.
The supporters refer to the "The Overseer, Wardens, Brethren and Sisters of the Fraternity or Guild of St. Andrew and St. Mary Magdalene, of Maidenhuth", which was formed in 1451. A purpose of this Guild, in addition to its religious duties, was "the continual reparation and keeping up of the bridge over the Thames". Here is the start of the corporate life of Maidenhead and its historic significance is recognised in the town's supporters.