There is believed to have been a school in Kirkcudbright from around 1455, the year the town became a Royal Burgh, the probable site being where the Roman Catholic Church now stands.

The first account of the school is in the Council Records stating that on 6th June, 1582, (during the reign of James VI), the Magistrates and Council “appoint William Turner, schoolmaster, to teach the grammar school, with salary of 50 merks, to be paid quarterly – viz., Candlemas, Beltane, Lammas, and Hallowe’en – and they to find him a sufficient schoolhouse, mail free.”

It is interesting to notice that at this time, and for some considerable time afterwards, only classics were taught in the school, and no records are found of any other schools or of any dame’s school having been in the town.

In 1766 the schoolhouse of Kirkcudbright was built. This was of one storey and contained two rooms, each 24 feet long and 17.5 feet wide. The precise date at which the school began to referred to as the ‘Academy’ is unknown, but English was reportedly taught for the first time in 1758. In 1765 the council appointed a school mistress to teach girls.

The first Academy building on the present site was constructed in 1818, at a cost of £1129. The Academy consists of 3 classrooms of spacious dimensions. Two of them are 45 feet in length and contain 9 large windows each. Kirkcudbright has long been famed for its educational advantages. The Academy has about an acre of ground belonging to it for the use of the scholars. The site of the building, with the ground was presented to the Burgh by the Earl of Selkirk.

In 1882, kirkcudbright Academy had 6 teachers and a school roll of about 160 pupils, with numbers split between Primary and Secondary. The Secondary part was divided into 3 departments, the department of Ancient and Modern languages, the Commercial and Mathematical department and the English Department.

The main building, built of whinstone, and dressed red sandstone, was designed by Alan B Crombie, and was built in 1901, incorporating the ealier school built in 1818. Further extensive reconstruction of the main building was carried out in 1926.

The Cochran Hall, designed by W.A. McKinnel was built in 1931 as a result of a donation by Thomas Cochran of New York in memory of his Kirkcudbright ancestors.

By the mid 1950’s the school buildings were severely overcrowded and pressure on classroom space had been relieved by the construction of temporary buildings. These were replaced in 1958 by a major extension.

By 1982 the Academy had over 800 secondary pupils and 52 members of teaching staff, with 17 subject departments.