There has been a Mayor of the town of Monmouth for at least 750 years.
The Romans had a base here before the Second Legion established its headquarters at Caerleon, the history of the town is generally recorded from the establishment of the Castle by the Norman Earl of Hereford, shortly after the Conquest (1066). Shortly afterwards a Benedictine priory was also founded.
By 1100 A.D. in addition to the Castle and the Priory a third party to the running of the town, the Burgesses had surfaced. This was as a result of the need to control the market in which the burgesses had a monopoly of trade. It was from this that the Common Council evolved and eventually the local government organisation, which exists to day.
An elected Mayor and bailiffs came to lead this body and by the middle of the thirteenth century a seal had been acquired from King Henry III with certain privileges. The office of Mayor can be dated from this time.
In 1447 Henry VI granted the first charter of "liberty and franchise" (freedom from certain royal taxes and the right to levy fees in relation to the market, etc). Amongst other matters it provided for the annual election of the Mayor, which survives to this day, as does the right for two maces to be borne before the Mayor. These maces bear the arms of the Duchy of Lancaster to which the Marcher lords of Hereford owed feudal duty.
In 1611 John Steed's book drew the first recorded map of the town, which shows that much of the centre remains unchanged. He says the town was governed by a Mayor, two bailiffs and fifteen Common Councillors and a Town Clerk. Apart from the bailiffs who acted with the Mayor as magistrates and an additional Councillor, this composition is identical to the present town council.