A keep, known as the Tower of Kingorne Wester, was in existence on the Rossend Castle site from 1119. It was later referred to as Burntisland Castle, and by 1382 was called Abbot's Hall, as it was the home of the Abbot of Dunfermline. The present building is largely of the 16th century, though with a 13th-century basement, which contains lancet windows and may represent the remains of a chapel. It was rebuilt by Peter Durie of Durie from 1552, and the arms of Abbot George Durie, and the date 1554, appear over the main door.

During the war of the Rough Wooing the English soldier John Luttrell landed at Burntisland on 28 December 1547. He burnt boats and buildings at the pier, and the owners of Rossend surrendered the castle to him.

Mary, Queen of Scots, visited during her short personal reign (1561–1567). On 14 February 1562, the French messenger and poet Chastelard was discovered hiding under Mary's bed in the castle.

On 11 May 1590 Sir Robert Melville hosted the Danish Admiral Peder Munk who was travelling to Falkland Palace to take possession of the lands granted to Anne of Denmark as part of her dowry.

In April 1594 James VI came to Rossend from Leith with his guard, and unsuccessfully tried to capture two rebel supporters of the Earl of Bothwell, Archibald Wauchope of Niddrie and John Wemyss of Logie.

The castle was acquired by the Town Council in 1952. In 1957, an early 17th-century painted timber ceiling was discovered; it is now in the National Museum of Scotland in Edinburgh. The ceiling includes the initials 'SRM' for 'Sir Robert Melville of Murdocairney' and emblems copied from the Devises Heroïques of Claude Paradin. The council threatened to demolish the property, which had been allowed to deteriorate, but it was saved after a public inquiry in 1972. It was bought in 1975 by the architecture firm Robert Hurd & Partners, who restored it and retain the building as their offices.

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Derbent Fortress

Derbent is the southernmost city in Russia, occupying the narrow gateway between the Caspian Sea and the Caucasus Mountains connecting the Eurasian steppes to the north and the Iranian Plateau to the south. Derbent claims to be the oldest city in Russia with historical documentation dating to the 8th century BCE. Due to its strategic location, over the course of history, the city changed ownership many times, particularly among the Persian, Arab, Mongol, Timurid, Shirvan and Iranian kingdoms.

Derbent has archaeological structures over 5,000 years old. As a result of this geographic peculiarity, the city developed between two walls, stretching from the mountains to the sea. These fortifications were continuously employed for a millennium and a half, longer than any other extant fortress in the world.

A traditionally and historically Iranian city, the first intensive settlement in the Derbent area dates from the 8th century BC. The site was intermittently controlled by the Persian monarchs, starting from the 6th century BC. Until the 4th century AD, it was part of Caucasian Albania which was a satrap of the Achaemenid Persian Empire. In the 5th century Derbent functioned as a border fortress and the seat of Sassanid Persians. Because of its strategic position on the northern branch of the Silk Route, the fortress was contested by the Khazars in the course of the Khazar-Arab Wars. In 654, Derbent was captured by the Arabs.

The Sassanid fortress does not exist any more, as the famous Derbent fortress as it stands today was built from the 12th century onward. Derbent became a strong military outpost and harbour of the Sassanid empire. During the 5th and 6th centuries, Derbent also became an important center for spreading the Christian faith in the Caucasus.

The site continued to be of great strategic importance until the 19th century. Today the fortifications consist of two parallel defence walls and Naryn-Kala Citadel. The walls are 3.6km long, stretching from the sea up to the mountains. They were built from stone and had 73 defence towers. 9 out of the 14 original gates remain.

In Naryn-Kala Citadel most of the old buildings, including a palace and a church, are now in ruins. It also holds baths and one of the oldest mosques in the former USSR.

In 2003, UNESCO included the old part of Derbent with traditional buildings in the World Heritage List.