The street would finally reach a length of nearly four miles (six kilometres), connecting the burgh to the neighbouring settlements of Linktown, Pathhead, Sinclairtown and Gallatown, which became part of the town in 1876.

[6] Four Bronze Age burials dating from around 4000 BC have also been found around the site of the unmarked Bogely or Dysart Standing Stone to the east of the present A92 road.

The battle was said to have been fought between the Angles and an alliance, led by King Áedán mac Gabráin of Dál Riata, of Scots, Picts and Britons.

[3][7] The first document to recognise the town was issued in 1075, when the King of Scots, Malcolm III (reigned 1058–93) granted the shire of Kirkcaladunt, among other gifts, to the church at Dunfermline.

In 1304, a weekly market and annual fair for Kirkcaldy was proposed by the Abbot of Dunfermline to King Edward I, during a period of English rule in Scotland from 1296 to 1306.

Under the status, responsibility would now lie with the bailies and council to deal with the routine administration of the town and its fiscal policies; conditional on an annual payment of two and a half marks (33s 4d) to the Abbot of Dunfermline.

[10] The town took advantage of its east coast location, which facilitated trading contacts with the Low Countries, the Baltic region, England, and Northern France.

In April 1598, the Grace of God, belonging to James Birrell of Kirkcaldy, was attacked off the Cape St. Vincent by the English Green Dragon of Bristol.

As a gesture, the king bequeathed 8.12 acres (3.29 ha) of common muir suitable for "bleaching of linen, drying of clothes, recreation and perpetuity".

[19] In 1813, the first Kirkcaldy whaling ship, The Earl Percy, sailed north to the Davis Strait; the town's last whaler, The Brilliant, was sold in 1866 to Peterhead, bringing an end to the industry.

[19] Construction of a new turnpike from Pettycur to Newport-on-Tay via Cupar in 1790, while improving only one section of Fife's isolated road system, brought a huge increase in traffic along Kirkcaldy's High Street, and helped to strengthen the town's position.

[20] To cope with increasing imports of flax, timber and hemp, and exports of coal, salt and linen, between 1843 and 1846 a new wet dock and pier was built at the harbour.

[21][22] In 1847 a canvas manufacturer, Michael Nairn, took out a licence on Frederick Walton's patent for the production of floorcloth, and opened a factory in nearby Pathhead.

[10][32] In the 21st century, Kirkcaldy remains an important centre for the surrounding areas, with a Museum and Art Gallery, three public parks and shopping facilities.

[35] The grant of feu-ferme status in the middle of the 15th century meant that the town could deal with its own administrative issues and fiscal policies for the first time.

[38] Kirkcaldy enjoyed royal burgh status until this rank was abolished in 1975 under the Local Government (Scotland) Act 1973, in favour of a three-tier system of regions and districts.

[18][60] The street eventually reached a length of nearly 4 miles (6.4 km), linking the burgh to its neighbouring suburbs of Linktown, Pathhead, Sinclairtown and Gallatown.

[18] Running back from the High Street were burgage plots or "rigs" of the burgesses; these narrow strips of land were at the front and to the rear of the houses.

The burn emerges from a deep-set culvert to flow under the Victoria Viaduct, down a deep gorge, through the site of Hutchison's Flour Mills before running parallel to the harbour wall and into the sea.

[72] The place of birth of the town's residents was 96.52% United Kingdom (including 87.15% from Scotland), 0.28% Republic of Ireland, 1.18% from other European Union countries, and 1.86% from elsewhere in the world.

[76] In June 2017, there was a recorded 1,000 Jobseekers Allowance (JSA) claimants in the Kirkcaldy area representing a 2.8% rate, which was higher than the Fife and Scottish averages.

[18] Early manufacturing both in Kirkcaldy and neighbouring Pathhead consisted of coarse cloth and nailmaking; the latter of which went to the Royal Master of Works for repairs at Holyrood Palace until the 17th century.

[35] This has been facilitated through a partnership between Forth Ports Ltd (the owners of the harbour), Hutchison's parent company of Carr's Flour Mills, and Transport Scotland, who provided a freight facilities grant of over £800,000.

[35] Kirkcaldy's town centre, which serves a large catchment area of around 130,000 residents within a 20-minute drive, is the largest in Fife in terms of retail floor space.

[98][99][100] The Adam Smith Theatre, the town's main auditorium, plays host to theatrical and musical productions as well as showing a selection of arthouse and commercial films.

[175][179] Ravenscraig is one of the earliest British castles designed to defend against and use artillery, an innovation demonstrated by the massive walls, the regularly placed shot holes, and the deep rock-cut ditch.

[225] Kirkcaldy is the birthplace of social philosopher and economist Adam Smith,[226] who wrote The Wealth of Nations at his mother's house at 220 High Street between 1765 and 1767.

[230] Politicians who come from the town include Henry Balnaves (ca.1512–1570) a Scottish politician, Lord Justice Clerk and religious reformer;[231] Ronald Munro Ferguson, the Governor-General of Australia from 1914 to 1920;[232] David Steel, leader of the Liberal Party from 1979 to 1988 and former Presiding Officer of the Scottish Parliament;[233] and Bertha Wilson, the first female judge of the Supreme Court of Canada and Court of Appeal for Ontario.

[241] Richard Park, the chief executive of Global Radio and the headmaster on the BBC talent show Fame Academy was born in the town.

The eminent zoologist, Prof David Raitt Robertson Burt (1899–1983) was born and raised in Kirkcaldy,[246] as was the botanist John Muirhead Macfarlane FRSE (1855–1943).