Montgomerieston, sometimes known as Montgomeryston (NGR NS 333 220) or Ayr Fort, was a small burgh of regality and barony of only 16 acres or 6.5 hectares located within the walls of the old Ayr Citadel, also known as Cromwell's Fort or Oliver's Fort, situated in the town of Ayr, South Ayrshire, Scotland. Montgomerieston was named for the Montgomerie family, Earls of Eglinton.
Under Oliver Cromwell five citadels were built in Scotland to control the Scots, such as at Leith, Perth, Inverlochy, Ayr and Inverness, with Ayr being the largest. The Ayr Citadel, built 1652-1653, was designed by the Dutch architect named Hans Ewald Tessin; it was constructed to a hexagonal plan with six bastions. Construction was far from easy with the sand substrate collapsing into pits and water flooding the workings. It had a moat filled with freshwater around it, 90 ft across at the curtain walls and 50 ft across at the bastions. The fort contained two or three 'bomb proof' magazines, one of which is said to have served as a gate.
After 1660 the citadel had been partly dismantled to prevent its use by persons hostile to King Charles II, although the moat was not infilled until around 1800. Wells were dug to provide an independent water supply for the soldiers. The seaward side of the fortifications were kept, possibly for use as a battery should the need arise.
After the restoration of the monarchy under King Charles II these citadels were erected as burghs. As recompense for the losses incurred by the Earl of Eglinton through his support of King Charles I the citadel at Ayr, as a burgh of regality and barony was given to the 7th Earl, Hugh who christened it 'Montgomerieston' after his family's name.
An additional reason for the gift to the Montgomerie family was that as Barons of Ardrossan much of their castle at Ardrossan had been dismantled and shipped Ayr to supply stone to build the citadel in the first place. The stone is of a similar type to that of Ardrossan Castle and the speed at which the citadel was constructed suggests that a ready supply of quarried stone was available. The cost of the construction was such that Cromwell is said to have commented Has it been built of Gold? Some of the stones carry mason's marks.