Dirleton is a 13th Century castle which stands on a rocky knoll, dominating the centre of the picturesque village of the same name. Constructed originally by the De Vaux family around 1225, it was one of the most formidable castles of its time. However, it was captured by an English army under Bishop Anthony Bek of Durham (1298) and was only recovered by Robert the Bruce in 1311. Bruce pulled down much of the castle to ensure the English armies could not make future use of it. Rebuilt in the 14th century by the Halyburton family, who added a new gatehouse, kitchen and Great Hall, it was further augmented by the Ruthven family in the 15th century, the castle passed to Sir Thomas Erskine (1566 - 1639) following the Gowrie Conspiracy. However, it was destroyed once again by General Monk (1650). It passed to the Nisbet family (1663), but was quickly abandoned as a residence in favour of their new and more comfortable house at Archerfield. Stone was looted from the site to build houses and walls in the local area.
Owned by the National Trust for Scotland, the castle is now in the care of Historic Environment Scotland. A substantial ruins remain, including the draw-bridge, chapel and a pit-prison. The ruins are surrounded by fine gardens, including the World's longest herbaceous border verified by the Guinness Book of Records in 1999 and a well-preserved beehive Doo'cot from 1550.