Castle Hill was the site of a castle held by three noble families, the MacDuffs - Thanes of Fife, the Stewarts - Earls of Fife and the Lauders. The first 13th century castle built of earth and timber, now called a motte, was held by the MacDuffs and illegally occupied by the English after the capture of Dirleton Castle by Bishop Beck in 1298. In 1314, Robert the Bruce defeated Edward II at the Battle of Bannockburn and Edward fled down the coast towards Dunbar pursued by James the 'Black' Douglas. The English garrison at North Berwick on hearing of their King's plight abandoned the castle and retreated to Dunbar. In the late 14th century a stone tower with barmkin was raised on the site by the Lauder family, who also constructed a keep on the Bass Rock. Castle Hill appears to have been abandoned in favour of the more secure Bass Rock Castle some time before the 1420s. Little remained of the castle when the site and its lands were given to the Abbey Nunnery in 1435.

By 1371 the barony of North Berwick had moved from the Earls of Fife into the hands of the Douglas family. The Douglases were modest landowners in Clydeside until the Wars of Independence brought them to prominence through Robert Bruce's friendship with Sir James Douglas. He was entrusted by King Robert to carry his heart into the Holy Land Crusades and his family adopted the Coat of Arms of a vivid red heart. The bond between the two families continued after their deaths culminating in Sir William Douglas being conferred Lord Douglas in 1358. The building of a great castle at Tantallon was William's way of proclaiming his new position among the landed gentry.

The name Tantallon derives from the Gaelic 'Dyn Talgwn' which means 'towering fortress'. In 1335, the inlet to the north west of Tantallon was a thriving fishing village and port for the surrounding countryside, which predates the castle. The prominence of the fortress was such that North Berwick was originally named Castleton. In 1389, Tantallon was in the ownership of Sir Malcolm Drummond through marriage, it then came back to the Douglases when Archibald, the Grim was established in the Douglas title and lands.

When King James II murdered William, Earl of Douglas his son the 6th Earl rose against the monarchy but was defeated and the Douglas lands were confiscated. King James II then re-enforced Tantallon, adding a new gate tower and raising the parapets on the battlements. When King James lost the Battle of Pinkie at Musselburgh in 1452 and died shorty after Tantallon returned to George Douglas, Earl of Angus, who set about heightening the ramparts to their present level. Sir Walter Scott was so impressed, he mentioned Tantallon in his poem Marmion - 'Tantallon, vast, broad, massive high and stretching far and held impregnable in war; On a projecting rock they rose, a round three sides the ocean flows'.By the middle of the sixteenth century the Lauder family held the Barony of North Berwick but following the death of William Lauder in 1569 who had no heirs, the land reverted back to the King who granted Alexander Home the rights. In 1633, Patrick Home sold the estate to Sir William Dick of Braid, a merchant and burgess of Edinburgh but later in the century he fell into financial difficulties and the estate was confiscated by the Commissioners of the Commonwealth. In 1650, the Moss Troops based at the castle caused so much damage to Cromwell's line of communication that in 1651 he sent an army out. The Roundheads under the command of General Monk bombarded the castle for twelve days and devastated the building to such an extent that the garrison surrendered. By 1694 Sir Hew Dalrymple took over the heritable debts of the estate and in 1699 purchased Tantallon Castle and later the Bass Rock from the Crown.

During the 1790s, the ruined castle was occupied by a gang of thieves who, headed by an old sailor, made their quarters in the inaccessible upper storeys of the keep, which they reached by means of a rope-ladder. They plundered the nearby farmhouses and mansions during the night, even going so far as to steal sheep off the fields. None of the gang were captured except one man, the others having gradually disappeared. This individual worked unsuspected through the day in the Rhodes lime quarries,until one evening a girl thinning turnips in a field at Castleton observed a man with a red cap looking out of a window of the fourth storey. After a long hunt he was captured by John Rennie tenant at Castleton who found him in a vault. He was later tried for his crimes in Edinburgh and transported.

The Duchess of Kent - mother of Queen Victoria visited Tantallon Castle on 26th September 1860 and His Royal Highness Prince Arthur Duke of Connaught - Queen Victoria's third son and godson of the Duke of Wellington visited on 29th August 1876. He was the guest of Sir Hew Dalrymple and following his visit, Sir Hew presented the Town Council with the gold badge and chain of office worn by the Provost, in appreciation of the loyal and respectful manner in which his guest had been received. Tantallon Castle has been in the ownership of the Dalrymple family since 1699 and is now maintained by Historic Scotland.

The land to the south of North Berwick was divided between Sir Hew Dalrymple of Leuchie (3039 acres) and Sir George Suttie of Balgone (8788 acres). Balgone House was built in the 15th century when it belonged to the Nunnery and Prioress in North Berwick. After the Reformation the estate was owned by several families including Lord Ross of Halkead, the Humes, Hepburns of Waughton, and John Semple WS whose daughter Marion in 1680 carried the property to her husband George Suttie, Baronet of Nova Scotia. His son Sir James Suttie married Agnes Grant and inherited her family estate of Prestongrange in 1818, when he assumed the name of Grant Suttie. The Prestongrange Colliery and Mansion House (now Royal Musselburgh Golf Clubhouse) remained with the Grant Suttie's of Balgone until 1958.'Nova Scotia' was the land where the esplanade of Edinburgh Castle now stands. This allowed Charles I, to grant a barony to any investor in the Canadian land known as 'New Scotland'. Sir Hew Dalrymple was also a baron of Nova Scotia.

Leuchie House was purchased from the Marjoribanks family in 1701. Sir Hew Dalrymple 2nd Baronet (1712-1790) demolished the old house and designed and built a new mansion over the old foundations in 1779. The building work took six years to complete. Leuchie was unoccupied for over fifty years until an extension and alterations were carried out and the absent landlord returned to Leuchie in 1859. The Dalrymple family also owned the property known as the Wall Tower (The Lodge in Quality Street) where the present Sir Hew Hamilton-Dalrymple was born in 1926. The name 'Wall' in this case derived from waal or well after St Andrew's Well which lay close to the mansion house. It is documented that a considerable sized distillery once stood on the high ground above the Wall Tower.

Since 1780 the farmers in the district and their guests visited the Bass Rock in July and dined at Canty Bay. The Bass dinner traditionally organised by the tenant at Blackdykes was held annually for over a hundred years. It was recorded that on one occasion twenty-four legs of lamb contributed by twenty-four farmers were prepared for the dinner by the Whitecross family innkeepers at Canty Bay for many years.

Beyond Blackdykes lies the farm of Gleghornie, where a village originally named Gleghorn once stood. Above the present farmhouse and steading are three tall ash trees marking the site of the old hamlet. In 1470 John Major was born in a thatched cottage at Gleghornie and was to become the most famous literary Scotsman of his generation. He was a champion of Medievalism as opposed to Renaissance ideas.

After studying at Cambridge and Paris, Major went to Glasgow, where among his pupils was John Knox. At St Andrews he taught Patrick Hamilton and George Buchanan. Later, Paris was to become his permanent headquarters where as professor at the University he published many of his books on philosophy, including the 'History of Greater Britain'. Major was proud of the fact that as the son of a humble ploughman, he had raised himself to be the friend and social equal of Gavin Douglas, born in the adjoining Tantallon Castle. John Major died at St Andrews in 1550, at the age of seventy-nine.

Halfland Barns, a small hamlet situated on a ridge south of Tantallon Castle, was known for its weavers around 1700, including the Watson and Gloag families. The Watson's had three sons who joined the navy, the youngest rose to the rank of Admiral. In 1775, he was appointed commander of the fleet in the Indian Ocean and assisted Clive to take Calcutta. Admiral Watson is buried in Westminster Abbey, where a monument was erected to his memory.

Further east stretch the estates of Auldhame, Seacliff and Scoughall, where the Christian missionary St. Baldred was based during the 8th century. Auldhame was so important in the life of the early church that it was recognised as a separate parish. Baldred also worshipped in the two neighbouring parishes of Hamer (Whitekirk) and Tyninghame. Although the small kirk's at Auldhame and Scoughall are long gone, many of the place-names still refer to the Culdee priest such as St. Baldred's Well and St. Baldred's Boat, a rock formation in the bay. Ghegan rock at Seacliff where the harbour is situated, means the 'Churchman's Haven'.

In mediaeval times Auldhame belonged to the Bishop of St Andrews, later the 16th century House of Auldhame was the home of Sir Adam Otterburn who was King's Advocate in the reign of James V and became Provost of Edinburgh. Robert Colt of Gartsherrie then purchased the land but was unable to maintain Auldhame House, which fell into ruin and he built a new house at Seacliff in 1750.

The estate passed to John Brodie then tenant of Scoughall, who in 1807 built the eastern portion of the Harbour Terrace at North Berwick for the storage of grain. He was followed by George Weir who was tenant for a single lease (19 years). George Sligo a merchant of Leith then purchased the land and employed David Bryce to extend Seacliff House in 1841. John Watson Laidlay, an Indigo manufacturer in Calcutta acquired the estate which then passed to his son Andrew. In 1890, he constructed the harbour on Ghegan Rock using a steam engine and compressed air to cut the stone. The harbour believed to be the smallest in Britain, was once busy with small cobbles working stake nets for salmon off the River Tyne. The ancient landmark on the South Car rock named St Baldred's Beacon was originally built by monks and rebuilt by the Laidlays.

Andrew Laidlay perished in a fire which destroyed Seacliff House (pictured left) in 1907 and is buried in the churchyard at Whitekirk. His brother John E. Laidlay, was a well known amateur champion golfer. In 1914, the surviving outbuildings at Seacliff House were commandeered by the Royal Navy as a top secret WW1 research station dealing with navigation techniques and U-Boat defence. The station was known as HMS Scottish Seacliff. In 1919, John R. Dale bought the estate after being tenant farmer of Scoughall since 1848, and Auldhame since 1834. The three estates remain to this day in the ownership of the Dale family. The novelist Robert Louis Stevenson was related to John Dale and spent several boyhood holidays at Scoughall. It was here in front of the farmhouse fire that the young Stevenson first heard the story of how folks in these parts on dark stormy nights, when winds used to lash the coast, lured sailing ships onto the rocks by displaying misleading lantern lights. These tales gave Stevenson the idea for his story called 'The Wreckers'.

The 'Pagans of Scoughall' had the worst of reputations, and were said to tie a horse's neck to its knee and attach a lantern to the rope. Then drive the horse slowly along the cliffs, so that a vessel out at sea would think it a ship riding at anchor, and come in, only to be wrecked on the rocky reef known as the Great Car and be plundered by the ghoulish people. Stevenson also wrote in his book 'Catriona' of the 'lights of Scoughall' and purposely put 'Tam Dale' in charge of the prisoners on the Bass Rock.

During the Napoleonic Wars the mouth of the river Peffer at Scoughall was thought to be a potential landing area for the French forces and army units were billeted in North Berwick in 1798. The stone building on the summit of Berwick Law was erected in 1803 as a signal station. Lieutenant Leyden was in command with a party of Naval Ratings who were instructed to light a beacon on the sight of enemy forces which would then start a chain of fires on high points across the country, providing an early warning system. The North Berwick regiment of volunteers commanded by Captain Robert Burns including those of Aberlady and Dirleton parishes were then ordered to assemble at North Berwick. They were to join and act with other troops and proceed to occupy the strong position of Whitekirk Hill and to oppose the landing of the French at Peffer Sands. The general orders were given at West Barns camp, 19th November 1803, by Major General George Don and if the enemy landed the local inhabitants were instructed to make for the Lammermuir Hills.