Provost Charles Hamilton (1704-1783) was, according to John Strawhorn ('History of Irvine', p.65), "the dominant figure of the period". The son of the laird of Ladyland in Kilbirnie parish, he came to Irvine as 'tide waiter', a customs officer who waited for ships to come into harbour and then checked their cargo. In 1740, he was enrolled as a burgess, not then an honorary title, but a freeman who, in return for the right to work and for protection from the unfree, assumed duties such as the payment of taxation, a share in the guarding of his town and also a share in its government. He rose to become Collector of Customs, responsible not only for the port of Irvine but for the coast from Troon to Largs, with a staff of fourteen. Salaries and fees brought him a considerable income of a hundred pounds a year.
From his elder brother he inherited the estate of Craighlaw in Wigtownshire, to which he added Garvoch in Renfrewshire, and local properties. In 1750 he became a councillor in Irvine. In the same year he acquired a feu at the quay and a lucrative monopoly for the Ship Inn of the sale of liquor at the harbour.
The great flood of 1769, a "great inundation", caused the River Irvine to change course at Tarryholm and to send down "immense quantities of sand" which choked the harbour (Strawhorn pp.83 & 76). Provost Hamilton organised major repairs, aided by a £150 grant from the Convention of Royal Burghs.
Hamilton resided at a house at the corner of High Street and Glasgow Vennel which later became the Porthead Tavern - the current Porthead Tavern is a rebuilt version of the original. He was wealthy enough that he was the first in the district, after the Eglinton family, to drive a closed carriage. During Robert Burns' stay in Irvine in 1781-82, he befriended the young poet and Burns struck up a firm friendship with his son John Hamilton, a medical student. Charles Hamilton served as Provost for six two-year terms between 1758 and 1781, and died in 1783.
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