The Smugglers Trail

Written by Gwen Sinclair

Five and twenty ponies,

Trotting through the dark —

Brandy for the Parson,

‘Baccy for the Clerk;

Them that asks no questions isn’t told a lie —

Watch the wall, my darling, 

While the Gentlemen go by!

“Hal o’ the Draft” – Puck of Pook’s Hill/The Smugglers Song 

By Rudyard Kipling (1865-1936)

After being hastily unloaded from Troon beach up to Dundonald Glen, The Smugglers’ Trail is an historic pathway which follows the secret route smugglers would have taken with their haul of contraband goods – to be spirited away for resale in Kilmarnock, Glasgow or Edinburgh. Starting or finishing at Dundonald Castle, this is a popular and varied walking route which meanders through ancient byways, woodlands, lochs, grassy parkland, beach, hill and glen. 

We have many visitors coming into Dundonald Castle Visitor Centre to find out more about The Smugglers’ Trail and have freely available copies of  the very useful route map publication: The Smugglers’ Trail Map – printed by South Ayrshire Council, South Ayrshire Waste and Environment Trust and Forward Scotland.  This has been developed as a walking trail in collaboration with Dundonald, Loans and Troon Community Councils with assistance from South Ayrshire Council. Following in the footsteps of the smugglers, the trail begins or ends on the path behind Dundonald Castle Visitor Centre – running parallel to the play park.  We’re always happy to assist in any way we can with those who want to enjoy a few hours exploring this delightful part of Ayrshire.

A lucrative business reputed to have used 500 local horses to help move the untaxed goods landed on the beach, The Smugglers’ Trail makes its way through Fullarton Woods, the haunt of the willow warbler, blackcap and great spotted woodpecker,  the ancient churchyard of Crosbie Kirk, the sparkling waters of the reservoir near Aught Woods, with fine views across to Isle of Arran on a clear day, passing Merkland Loch, and onwards into the ancient woods at Dundonald – rich in bird song and in tales of local smuggling encounters with government dragoons!

It seems that big scale smuggling began with the emergence of spiralling taxation by successive monarchs, roughly starting in England with Edward III (1327-1377).  Developed as a way to help fund The Hundred Years’ War (1337–1453), where taxation began mainly on imported wine, but by the time of the Tudors, import duties became payable on almost all imported items. However imposing taxes and the collecting of them was another story!   By the 15th century enforcement agencies in England began to appear at major ports which evolved into government customs and excise authorities – but these only worked if goods were brought into an official port! 

In Scotland prior to the Act of Union in 1707 smuggling mainly consisted of goods going into England for businesses based there to avoid import taxation, or to get away with paying the unpopular whisky excise duty which began to be levied in Scotland in 1644 – when 2 shillings and 8 pence was supposed to be paid on ‘everie pynt of aquavytie or strong watteris sold within the countrey.’

Preacher and Philanthropist Thomas Guthrie (1803-73) from Brechin noted in his memoirs from the early 19th Century: ‘Everybody, with few exceptions, drank what was in reality illicit whisky – far superior to that made under the eye of the Excise – lords and lairds, members of Parliament and ministers of the gospel.’  Indeed it’s thought that Dunure, Maidens, Turnberry and Culzean were landing places for whisky – or ‘the Arran Watter’ – which was whisky distilled illicitly and brought in from the Isle of Arran.

The general smuggling of rum, gin, tobacco, tea, brandy, oats, salt and silk became as prevalent in Scotland as it was in England when The Scottish Excise Board was established in 1707 as part of the Treaty of Union. This was brought in to attempt to enforce the collection of import duties in line with England, and found Scots with an almost seven-fold increase to import taxes – of which many imported goods had hitherto been tax-free such as salt and malt – both seen as essential commodities for every day life.  

“Smuggling was almost universal in Scotland for people unaccustomed to imposts and regarding them as an unjust aggression upon their ancient liberties, made no scruple to elude them whenever it was possible to do so.” Sir Walter Scott (1771-1832)

Rumour has it that Troon became the most efficient and extensive smuggling ring in the whole of the British isles!  It’s natural harbour provided shelter from the wind, making it the ideal place to land highly taxed goods – with much of it coming from the Isle of Man, where custom taxes were much lower. Giving an idea of the scale of the smuggling operation, in order to try and police it, the government authorities found themselves in need of regular back-up from redcoats stationed at Ayr and Irvine!  

Ailsa Craig 1850 by Robert C. Carrick – National Galleries of Scotland Creative Commons by CC by NC

It’s said that at low tide over a dozen Manx wherries –  largely open vessels capable of carrying modest loads – could have been seen berthed on the shores of Troon! These boats would come up the coast from Ballantrae and lurk around Ailsa Craig before being run up the sands at Barassie or at Troon – where the Smugglers’ Trail starts or ends depending on what direction you choose to take. The swag was then spirited away along The Smugglers’ Trail using horse-drawn carts or by shank’s pony, to Dundonald, with various stop-off locations en route used hide the contraband items from the excise men, before being later sold on.

The Smugglers’ Trail takes you through Loans – where you might pause to wonder which of the houses had Brandy Holes – literally holes either dug outside or concealed storage spaces behind faux walls especially built within the houses – just a little wider than an oak cask – which was an ideal spot to squirrel away untaxed goods! Interestingly in the 19th Century, Loans had two toll bars which gated the road and required the-parting-of-funds, or tolls, in order to travel onwards, and it seems the toll guards furthered their income by selling – you’ve guessed it – alcoholic beverages! 

Map of Dundonald and Newfield 1811 By Roger Griffith – William Aiton – – Agriculture of the County of Ayr, Public Domain,

Dundonald Castle is thought to have been abandoned and left to ruin by 1726, until it was gifted to the State in 1953 by the 13th Earl of Dundonald, when work began then to preserve it from further deterioration.  This would fit in nicely with the timeline of known smuggling in the area. In all probability Dundonald Castle could then have made for a very useful location to hide contraband goods from the prying eyes of the Government exciseman – with plenty of nooks and crannies inside that could easily hide contraband goods.  There is also a hollow part underneath the ground floor which indicates that there were reasonable sized cellars there prior to the fitting of the flag stones we see here today. This could have been an ideal spot for smugglers! Furthermore Castle Hill could well have served as an ideal look-out post for government officials making their way through the woods! 

In the old statistical account of Dundonald Parish [Vol. VII, pages 615–625]  c.1792, compiled by the Reverend Robert Duncan, Minister of Dundonald 1783-1815, who is the ‘Duncan deep’ in the Robert Burns’ poem ‘The Twa Herds; or The Holy Tulyle, An Unco Mournfu’ Tale’ which stated:

The British government gave the first check to smuggling upon this coast, by purchasing the regal power of that petty state. Happily the Commutation Act1 has nearly annihilated the hostile traffic. It must be acknowledged, that lessening some duties to a certain degree would not injure the revenue; and yet more effectually cut up this business with a fleet of cutters, or an army of custom and excise officers. Uncontrovertible evidence must convince every attentive man, living upon the coast of Ayrshire, of the great wisdom of the apostle, in joining those two precepts in one sentence, ‘Fear God, Honour the King’.  Smuggling, in its very nature, tends to weaken in the dealer that sense which he has of lawful authority, to disturb his peace, to injure his health, to corrupt his manners. Must it not be regretted, that men of amiable dispositions should be seduced by the temptations of this trade. Were profit and loss upon it clearly calculated, the balance would be much against the profit side, putting health and peace and character out of the question.” 

 A dire warning indeed from the Reverend Duncan!

1The Commutation Act of 21 June 1784 was passed as an attempt to stop tea smuggling. It reduced the tax on tea from a whopping 119% to 12.5%. It also elected to have all past smuggling misdemeanours forgiven. 

David Dunlop Grave from ‘A Smugglers lament’ film for FoDC by Marysia Kolodziej

An audacious contraband operation was led by local miller, David Dunlop, whose smuggling business – Dunlop & Co – began in the 1740s and was said to have lasted 40 years! He is buried under a flat stone near the centre of the graveyard at Dundonald Parish Church. There was once a stone there too for fellow smuggler and convicted murderer, Matthew Hay,  but it has long since disappeared.

Further Details of the Smugglers’ Trail Walking route:

Watch a short film following the Smugglers’ Trail by Dawn-Marie – Love Exploring Scotland:

We have copies of the Smugglers’ Trail leaflet outlining the route available free from Dundonald Castle Visitor Centre, and outside you will also find an information board beside the car park which shows details for the route. 

Find online versions of the Smugglers’ Trail Map here:

It is well worth checking out:  and  for more details of the Smugglers’ Trail walk.

You may wish to park at Dundonald and begin your adventure down the Smugglers’ Trail from here.  If you want to do it just one way – bus times from Troon to Dundonald or Dundonald to Troon can be found here:

We are planning to host a Book Launch at Dundonald Castle Visitor Centre on 18th September 2021 for The Dundonald Smugglers Revisited by Frances Wilkins. Watch out for further details on how to book your seat for this event on our social media. Frances has written over a dozen books on the subject of smuggling and some are available for sale at our gift shop at the Visitor Centre. For more details on France’s books check out her website:

Sources: .Page 15.


Smugglers Trail signposts-screenshot: from Smugglers Trail film by Dawn-Marie

David Dunlop Grave from ‘A Smugglers lament’ film for FoDC by Marysia Kolodziej 

Ailsa Craig 1850 by Robert C. Carrick – National Galleries of Scotland Creative Commons by CC by NC

Map of Dundonald and Newfield 1811 By Roger Griffith – William Aiton – William Aiton – Agriculture of the County of Ayr, Public Domain,

Bottle on the beach Image by 8249023 from Pixabay