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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Broch of Gurness

The Broch of Gurness is an Iron Age broch village. Settlement here began sometime between 500 and 200 BC. At the centre of the settlement is a stone tower or broch, which once probably reached a height of around 10 metres. Its interior is divided into sections by upright slabs. The tower features two skins of drystone walls, with stone-floored galleries in between. These are accessed by steps. Stone ledges suggest that there was once an upper storey with a timber floor. The roof would have been thatched, surrounded by a wall walk linked by stairs to the ground floor. The broch features two hearths and a subterranean stone cistern with steps leading down into it. It is thought to have some religious significance, relating to an Iron Age cult of the underground.

The remains of the central tower are up to 3.6 metres high, and the stone walls are up to 4.1 metres thick. The tower was likely inhabited by the principal family or clan of the area but also served as a last resort for the village in case of an attack.

The broch continued to be inhabited while it began to collapse and the original structures were altered. The cistern was filled in and the interior was repartitioned. The ruin visible today reflects this secondary phase of the broch's use.

The site is surrounded by three ditches cut out of the rock with stone ramparts, encircling an area of around 45 metres diameter. The remains of numerous small stone dwellings with small yards and sheds can be found between the inner ditch and the tower. These were built after the tower, but were a part of the settlement's initial conception. A 'main street' connects the outer entrance to the broch. The settlement is the best-preserved of all broch villages.

Pieces of a Roman amphora dating to before 60 AD were found here, lending weight to the record that a 'King of Orkney' submitted to Emperor Claudius at Colchester in 43 AD.

At some point after 100 AD the broch was abandoned and the ditches filled in. It is thought that settlement at the broch continued into the 5th century AD, the period known as Pictish times. By that time the broch was not used anymore and some of its stones were reused to build smaller dwellings on top of the earlier buildings. Until about the 8th century, the site was just a single farmstead.

In the 9th century, a Norse woman was buried at the site in a stone-lined grave with two bronze brooches and a sickle and knife made from iron. Other finds suggest that Norse men were buried here too.