CUPAR, a royal, municipal and police burgh, and capital of the county of Fifeshire, Scotland, 11 m. W. by S. of St Andrews by the North British railway. Pop. (1901) 4511. It is situated on the left bank of the Eden, in the east of the Howe (Hollow) of Fife, and is sometimes written Cupar-Fife to distinguish it from Coupar-Angus in Perthshire. Among the chief buildings are the town hall, county buildings, corn exchange, Duncan Institute, cottage hospital, Union Street Hall and the Bell-Baxter school. The school, formerly called the Madras Academy, was originally endowed (1832) by Dr Bell, founder of the Madras system of education, but, having been enriched at a later date by a bequest of Sir David Baxter (1873), it was afterwards called the Bell-Baxter school. The Mercat Cross stands at “the Cross” in the main street, where it was set up in 1897, having been removed from Hilltarvit, an eminence in the neighbourhood of Cupar, on the western slope of which, at Garliebank, the truce was signed between Mary of Guise and the lords of the Congregation. In the parish, but at a distance from the town, are the Fife and Kinross asylum and the Adamson institute, a holiday home for poor children from Leith. The town received its charter in 1356 from David II., and, being situated between Falkland and St Andrews, was constantly visited by Scottish sovereigns, James VI. holding his court there for some time in 1583. The site of the 12th-century castle, one of the strongholds of the Macduffs, thanes or earls of Fife, is occupied by a public school. On the esplanade in front of Macduff Castle, still called the Playfield, took place in 1552 one of the first recorded performances of Sir David Lindsay’s Ane Satyre of the Three Estaits (1540); his Tragedy of the Cardinal (1547), referring to the murder of Beaton, being also performed there. Sir David sat in the Scottish parliament as commissioner for Cupar, his place, the Mount, being within 3 m. north-west of the town. Lord Chancellor Campbell (1799–1861) was a native of Cupar.
Cupar is an agricultural and legal centre. Its chief industry is the manufacture of linen, and tanning is carried on. At Cupar Muir, 1½ m. to the west, there are a sandstone quarry and brick works. The town has also some repute for the quality of its printing, both in black and colour. This was largely due to the Tullis press, which produced about the beginning of the 19th century editions of Virgil, Horace and other classical writers, under the recension of Professor John Hunter of St Andrews, which were highly esteemed for the accuracy of their typography. Cupar belongs to the St Andrews district group of burghs for returning one member to parliament, the other constituents being Crail, the two Anstruthers, Kilrenny, Pittenweem and St Andrews.
There are several interesting places within a few miles. To the north-east is the parish of Dairsie, where one of the few parliaments that ever met in Fife assembled in 1335. The castle in which the senate sat was also the residence for a period of Archbishop Spottiswood, who founded the parish church in 1621. Two miles and a half north of Dairsie is situated Kilmany, which was the first charge of Thomas Chalmers. He was ordained to it in May 1803 and held it for twelve years. David Hackston, the Covenanter, who was a passive assister at the assassination of Archbishop Sharp, belonged to this parish, his place being named Rathillet. After his execution at Edinburgh (1680) one of his hands was buried at Cupar, where a monument inscription records the circumstances of his death. To the west of Kilmany lies Creich, where Alexander Henderson (1583–1646), the Covenanting divine and diplomatist, and John Sage (1652–1711), the non-juring archbishop of Glasgow, were born. Henderson took a keen interest in education and gave the school at Creich a small endowment. Some 3 m. to the south-west of Cupar is Cults, where Sir David Wilkie, the painter, was born. His father was minister of the parish, and Pitlessie, the fair of which provided the artist with the subject of the first picture in which he showed distinct promise, lies within a mile of the manse. In the sandstone of Dura Den, a ravine on Ceres Burn, 2½ m. E. of Cupar, have been found great quantities of fossils of ganoid fishes. The rocks belong to the Upper Old Red Sandstone.