In early times, because of their rock-bound shores and jagged aspect, Auchenmalg Bay and Portyerrock served as common landing places for Galloway smugglers bearing cargoes of spirits, tobacco, silk, wine, and candles from foreign lands to lucrative markets in Ayr, Paisley, and Edinburgh. Smuggling was known as free trading, being an illegal way of avoiding customs duties and burgh taxes.
Smugglers landing at Auchenmalg Bay, often under the headland of Synniness, moved along Gillespie Glen and Burn towards the Knock of Luce, then turned eastwards past Annabaglish farm, and forded the Tarff at its most southerly bend. They followed the river from Kenmore to Barnearnie and then moved on into Kirkcowan.
Smugglers from the Whithorn area also came into the village, or passed by it, on their routes to Ayr.
As many as 50 or 60 of the illegal packmen, each man having borne several kegs of the contraband goods on horseback from the coast, would often stop at one of the several Kirkcowan inns for breakfast at dawn.
The Thatch Inn, Stay the Voyage (known locally as Stiravage), and Nancy Shepherd’s -inn near Kiltersan were known haunts of the smugglers.
From Kirkcowan some took the routes to Ayrshire via Nick o’ the Balloch or Straiton, while others struck off to use a lonely path beyond Minnigaff, past Loch Trool and Loch Enoch, continuing to Dalmellington.