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Accounts date the construction of the castle to 1421 when Sir John Wemyss decided to build a fortified castle to replace one destroyed by the Duke of Rothesay at Kilconquhar in 1402. The castle is thus the ancient seat of the Earls of Wemyss and their families. Historically, the castle is perhaps best known as the location where Mary, Queen of Scots, met her future husband Lord Darnley, in 1565.
Wemyss is an imposing castle sitting high atop cliffs with a view over the Firth of Forth. Two particular points of interest are that one of the towers from an earlier building has been re-used, first as a windmill and later as a dovecote. There is also an oval-shaped dungeon within the castle, connected to the building by a 30m zigzag passage. Wemyss castle was restored in the 1950s and remains a residence. Members of today's Royal Family, including the Queen, have visited.
Some believe Wemyss possesses, like a number of Scottish castles, a "Green Lady". Green, in Scotland at any rate, has always been an unlucky colour, associated with death and misfortune. Particularly unfortunate is the girl who wears green on her wedding day. In the case of Wemyss, the ghost is that of a young woman wearing a trailing dress of green silk which rustles as she floats along the corridors within the castle. A news report in 2007 suggested that sightings had ceased in recent years.
- "Beware the witching hour". Fife Today. 30 October 2007. Retrieved 15 March 2012.