The name is Gaelic at its root: Cille Chuithbeirt - 'chapel of Cuthbert.' Saint Cuthbert was the great Northumbrian holy man whose body, exhumed from Lindisfarne in 875 to keep it from the Vikings, was carried through northern Britain for over a century before its final reinterment at Chester-le-Street. Kirkcudbright was one of the resting places along that wandering, and the chapel built to shelter the saint's bones gave the place its name. By 1455 Kirkcudbright was a royal burgh; by the time of Mary, Queen of Scots, Sir Thomas MacLellan of Bombie was dismantling the old Franciscan convent to build his new castle on the site. MacLellan's Castle still stands on the harbourfront, roofless but proud.

Kirkcudbright has had a strange relationship with English royalty. In 1300, during his war against Scotland, Edward I is said to have stayed in the ancient castle at Castledykes. In August 1461, after the catastrophic Lancastrian defeat at the Battle of Towton, Henry VI of England crossed the Solway Firth and landed here on his way to exile in Linlithgow with Queen Margaret. In 1547 the town withstood a siege by the English commander Sir Thomas Carleton - until the surrounding countryside was overrun and Kirkcudbright was forced to surrender. The Tolbooth on the High Street, built between 1627 and 1629, held John Paul Jones - celebrated naval officer of the American Revolution - in 1770 over the death of a sailor he had ordered flogged. He was acquitted.

The colony that turned Kirkcudbright into 'the Artists' Town' began arriving around 1880. The Glasgow Boys - a loose grouping of painters reacting against the sentimental Victorian establishment - found in Galloway a landscape that rewarded their interest in light, weather, and ordinary working people. They were followed by the Scottish Colourists: Samuel Peploe and Francis Cadell among them, who brought a bolder, more French palette. Edward Hornel, George Henry and Jessie M. King moved here from Glasgow. Later, Robert Sivell and John Charles Lamont built studios across the river at The Stell. Landscape painter Charles Oppenheimer arrived in 1908 and stayed; in 1956, with artist Dorothy Nesbitt, he saved the Harbour Cottage Gallery from demolition. The colony is still here. Wasps Studios occupies two linked townhouses on the High Street. The Spring Fling open-studios event runs every May.

The Tolbooth is now an arts centre. The 1879 Town Hall, designed by Edinburgh architects Peddie and Kinnear, was converted into the Kirkcudbright Galleries and opened by the Princess Royal on 12 July 2018. The Stewartry Museum, founded in 1879, holds Britain's earliest surviving sporting trophy - the Siller Gun, a small silver gun awarded for shooting competitions. The Kirkcudbright Railway opened in 1864 and was closed in 1965 under the Beeching cuts; the tracks are gone, the station is gone, but the line of the embankment is still visible if you know where to look. The war memorial, by sculptor George Henry Paulin, dates from 1921.

Kirkcudbright has lent its narrow streets and red-stone walls to surprising amounts of British screen work. The 1973 cult horror film The Wicker Man used several locations here. In 1975 the BBC adapted Dorothy L. Sayers' Five Red Herrings - a Lord Peter Wimsey whodunit set explicitly in the town's art world - with Ian Carmichael in the lead. Robert Urquhart starred in a 1980 BBC adaptation of Ibsen's An Enemy of the People, also shot here. The composer Cecil Coles was born in Kirkcudbright in 1888 and killed in the First World War in 1918. Marriott Edgar - who wrote the much-loved monologue Albert and the Lion for Stanley Holloway - was born here in 1880. And T. E. Lawrence, 'Lawrence of Arabia,' lived in infancy at Craigville, St Mary's Street, between 1889 and 1891.