Kirkcaldy, United Kingdom

The Battle of Raith in AD 596 was once believed to have taken place to the west of the town's site but the theory no longer holds support. 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.

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. The residents were expected to pay dues and taxes for the church's general upkeep. Two charters, later confirmed by Malcolm's son David I in 1128 and 1130, refer to Kircalethin and Kirkcaladunit respectively, but do not indicate their locations.

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. During these discussions, the town may have been referred to as "one of the most ancient of burghs". This status as a burgh dependent on Dunfermline Abbey was later confirmed in 1327 by Robert I, King of Scots.

A charter granted in 1363 by David II, King of Scots (reigned 1329–1371), awarded the burgh the right to trade across the regality of Dunfermline. This charter allowed the burgesses of Kirkcaldy to purchase and sell goods to the burgesses of the three other regality burghs – Queensferry, Dunfermline and Musselburgh – that belonged to the Abbey. By 1451, Kirkcaldy was awarded feu-ferme status. 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.

At the beginning of the 16th century, the town became an important trading port. The town took advantage of its east coast location, which facilitated trading contacts with the Low Countries, the Baltic region, England, and Northern France. The feu-ferme charter of 1451 between the Abbot of Dunfermline and the burgesses of Kirkcaldy mentioned a small but functioning harbour; it is not known when this harbour was established, or whether it was always located at the mouth of the East Burn. According to treasurers' accounts of the early 16th century, timber imported via the harbour—possibly from the Baltic countries—was used at Falkland Palace and Edinburgh Castle, as well as in shipbuilding.

Raw materials such as hides, wool, skins, herring, salmon, coal and salt were exported from the town until well into the 17th century. Ships from Kirkcaldy brought wine and spices from Spanish ports including Cádiz. 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. Birrell's ship sank and the mariners who reach the shore were in danger of being made captive by Turkish authorities.

A charter issued by Charles I granting royal burgh status in 1644 resulted in the end of the Abbey's jurisdiction over the town. 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". In 1638, under the reign of Charles I, the town subscribed to the National Covenant, which opposed the introduction of episcopacy and patronage in the Presbyterian church. Support for the Covenanting cause cost the town over 250 men at the Battle of Kilsyth in 1645. The continuing civil wars killed at least another 480 men and led to the loss of many of the harbour's trading vessels. By 1660, this left the town with only twelve registered ships, down from 100 it is claimed were recorded between 1640 and 1644.

Towards the end of the 17th century, the economy recovered, with growth in manufacturing. During this period, Daniel Defoe described Kirkcaldy as a "larger, more populous, and better built town than ... any on this coast". A shipbuilding revival produced 38 vessels between 1778 and 1793. In the mid-19th century, whaling became important to the town for a short time. 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. 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.