Sir Brian O’Neill claimed the lands of Lower Clandeboye, Upper Clandeboye and the Great Ardes, and had been knighted in 1568 for his service to the Crown. However he fell out of favour with the Queen and adopted a scorched earth policy, burning the abbeys, priories and major buildings across the region to prevent any incoming English army using them as garrisons.

Sir Henry Sidney was the Queen’s Lord Deputy in Ireland. He visited the O’Neill lands in 1575, after Sir Brian’s scorched earth tactics, and declared the region to be “all waste and desolate”, due to the wars and rebellions which had taken place during the failed settlement attempts by Sir Thomas Smith in 1571 and the Earl of Essex in 1573. (quote from The Montgomery Manuscripts, page 79)

Hugh Montgomery completed his education at Glasgow College and headed for the Continent, where he served for a number of years under Prince William I of Orange, as Captain of Foot of a Scottish Regiment. When Montgomery’s parents died around 1586 he returned to Scotland to become the Sixth Laird of Braidstane, and was described as “...a well-accomplished gentleman...”. (quote from The Montgomery Manuscripts, page 10)

Hamilton left his home in Dunlop, Ayrshire (where his father Rev. Hans Hamilton was minister of the church) and was educated at St Andrews University. He left Scotland and arrived in Dublin - storms forced the ship he was in to dock there. He and fellow Scot James Fullerton decided to stay and they opened a school. In 1591 they were appointed founding Fellows of Trinity College, and also became agents for King James VI of Scotland, reporting to him about Queen Elizabeth I’s activities in Ireland.

Sir Brian’s lands eventually passed to his grandson Con O’Neill around 1586, who lived in the Anglo-Norman “Castle Reagh” or “Castle Clannaboy” overlooking the village of Belfast. His troops were caught in a skirmish with the Queen’s troops, at least one of whom was killed. Con was arrested and imprisoned in Carrickfergus Castle, destined for execution. In fact, Sir Arthur Chichester made an offer to the Queen to hang Con without a trial - perhaps so he could claim Con’s lands for himself?

The Queen whom Con was charged with “levying war” against was now dead, and Chichester’s opportunity was gone. Queen Elizabeth had no children, and so the throne passed to her next of kin, King James VI of Scotland. Official news of her death was brought to the King by James Hamilton, who was involved in negotiations for the King’s accession to the throne of England.

King James VI of Scotland brought his courtiers and advisors to London on 3rd April 1603 (escorted by Hugh Montgomery) and became King of England and Scotland on 25th July – an event known as “The Union of the Crowns”. The new King knighted Hamilton’s long-term associate and fellow Dublin agent James Fullerton, granting him Olderfleet Castle near Larne, County Antrim.

The death of Elizabeth I and the accession of King James VI to the throne of England saw a major shift in the balance of power across the British Isles. Con’s wife, Ellis O’Neill, recognised the opportunity, and she put a plan to Hugh Montgomery - free Con from Carrickfergus and secure a Royal pardon from the new King, and the reward will be half of the O’Neill lands. Montgomery accepted.

Hugh Montgomery sent an Ayrshire relative and sea-trader, Thomas Montgomery, to Carrickfergus to free Con O’Neill. Thomas romanced Annas Dobbin, the daughter of the Town Marshall, befriended her father and used his influence to gain access to the Castle. Thomas sprung Con from his cell, they boarded Thomas’s boat and sailed across the North Channel to Largs, close to the Clan Montgomery castles of Ardrossan, Brodick and Skelmorlie.

Con O’Neill and Hugh Montgomery finalised their deal at Braidstane Castle, Hugh Montgomery’s home, and travelled to London to win the King’s approval and Con’s Royal Pardon. However, James Hamilton discovered the plan and intervened. He sent Sir James Fullerton to convince the King that O’Neill’s lands should be divided into three, with 1/3 for James Hamilton.

King James accepted this proposal and approved the three-way split, with 1/3 each for Hamilton, Montgomery and O’Neill. Montgomery and O’Neill were furious, but the deal stood. Con O’Neill was pardoned and he and Montgomery travelled back to Scotland and then across to Ulster, where Con returned to a hero’s welcome at Castle Reagh.

During Hugh Montgomery’s time in London, he renewed his friendship with some of King James’ courtiers and advisors, creating an opportunity for his brother George (the Dean of Norwich) to gain in Ulster. King James appointed George Montgomery as Bishop of Derry, Raphoe and Clogher on 13th June 1605 - just six weeks after the three-way deal was finalised.

With the agreement signed, O’Neill, Hamilton and Montgomery began to trade and sell lands with each other in a complex set of transactions from June 1605 until May 1606.

Back in London, one of the most famous events in world history took place almost destroyed everything they had been working towards...

Guy Fawkes and Hugh Montgomery had fought on opposing sides during the wars in Holland in the late 1500s. On 5th November 1605, Fawkes’ Gunpowder Plot was foiled and he was arrested. An emergency session of the King’s Privy Council was held early that morning, and Fawkes was brought in under arrest. When questioned by the King, Fawkes replied that his intentions were “... to blow the Scotsmen present back to Scotland ...”. If the Gunpowder Plot had succeeded the Settlement may never have taken place. (quote from Guy Fawkes by WH Ainsworth, 1841, page 260)

Hamilton and Montgomery sent communications to Scotland to encourage people to take advantage of the new lands in Ulster. Both men convinced their extended families to join them in the settlement scheme and, in May 1606, the first waves of settlers – farmers, stonemasons, builders, carpenters, textile workers, merchants and clergymen – sailed across the narrow channel of water and arrived in Ulster to form the backbone of the new Ulster-Scots community.

“... about the towns of Donaghadee and Newton ... in the spring time, Ao. 1606, those parishes were now more wasted than America ... 30 cabins could not be found, nor any stone walls, but ruined roofless churches, and a few vaults at Gray Abbey, and a stump of an old castle in Newton ...”

This scene was transformed:

“... the harvests of 1606 and 1607 had stocked the people with grain, for the lands were never naturally so productive since that time ...”

(both quotations from The Montgomery Manuscripts, pages 58 and 62)
[ 13th May 1607 – Jamestown Settlement, Virginia ]

Hugh’s brother, Bishop George Montgomery, arrived in Ulster with his wife in October 1606. In Spring 1607 they started to accept Scottish tenants from Glasgow, Ayr, Irvine, Greenock and the south west of Scotland. Over the next three years many Scots settled on his church lands in Donegal and Londonderry.

(See The Scottish Migration to Ulster by M Perceval-Maxwell, 1973, page 69)
[ 4th September 1607 - Flight of the Earls ]

In July 1607, King James was so pleased with the progress of the Settlement that he wrote to Sir Arthur Chichester, in response to a request from Hamilton, that Bangor, Coleraine and Belfast should be granted charters for incorporation, “... for the better setling and incouraging of the new Colonies of English and Scotish which do daylie endeavour to make Civill plantacion in Downe and Antryme ...”
(quoted from The Scottish Migration to Ulster by M Perceval-Maxwell, 1973, page 57)
[ September 1610 – Plantation of Ulster begins ]

Montgomery travelled from Donaghadee to Newtownards, where he repaired the ruined Priory. It was ready for service before the winter of 1607. Hugh’s wife Elizabeth took on the task of building water-mills, establishing farms, introducing textile manufacturing (linen and tartan). They established a regular market in the town. Hugh built a school in Newtown and brought, archery, golf and football!

They reported “... Sir Hugh Montgomery hath repaired Newtown for his own dwelling and made a good town of a hundred houses all peopled with Scots ...”

“Sir James Hamylton, Knight, hath buylded a fayre stone house at the towne of Bangor... about 60 foote longe and 22 foote broad; the town consists of 80 newe houses, all inhabited by Scotyshemen ...” Bangor Town Hall is on the site of Hamilton’s original home.

(quote from The Montgomery Manuscripts, page 85 / from Ulster – The Founding Fathers by EM Griffith, page 4)

Such was the success of the settlement that Hamilton & Montgomery were returned as Members of Parliament for County Down. Newtown was made a borough, with a provost and burgesses and the right to return two members to Parliament. William Edmonston, one of Montgomery’s major tenants, invited Rev Edward Brice to Ballycarry in this year – the first Presbyterian minister in Ulster.

[ 1621 – Plantation of Nova Scotia is granted ]

Montgomery was made the first Viscount of the Great Ards on 3rd May 1622, with Hamilton made the first Viscount Clandeboye the next day. This was their reward for
“... the pacifying of Clandeboye, after rebellion, in the tumults of the peasants of Ulster; also, in pacifying of Ardes, in our kingdom of Ireland, a colony of Scots being brought in the beginning of our reign over from Great Britain into Clandeboye and Ardes ...”
(quote from The Hamilton Manuscripts, page 13)

Due to ongoing boundary disputes with Montgomery, Hamilton commissioned London cartographer Thomas Raven to map his estates. Raven was already working in Ulster, mapping the London Companies areas in the Plantation of Ulster in County Londonderry. The Hamilton Raven Maps are on public display at North Down Heritage Centre in Bangor.

Hugh Montgomery died in 1636 and was buried at Newtownards Priory with a Scottish State funeral on 8th September. The next morning the “Eagle Wing” set sail from Groomsport Harbour, bound for the New World. James Hamilton died in 1644 and was buried at Bangor Abbey – both are without memorials.

But the impact of their settlement lives on, right up to the present day. The origin of Ulster-Scots traditions, values and cultural expression can be traced back to the settlers who arrived with Hamilton and Montgomery. It is right that we recognise the achievements of these two men, their families and the ordinary settlers who sailed across the North Channel to establish the first Ulster-Scots community.