Sinclair of Dryden

The following descendant table commences with William, third son of Henry St. Clair, 1st Earl of Orkney and Jean Halyburton, daughter of Sir Walter Halyburton of Dirleton in East Lothian. The first reference to William in source documents notes that he and his brother John, together with eight servants, were granted safe conduct in 1405 by the English King Henry IV for six weeks to go to England where their brother Henry, 2nd Earl of Orkney, was being held prisoner in Durham castle. A second reference is on 20 November 1407 when he was a witness to the gift to his brother Henry and his wife Egidia Douglas of the barony of Herbertshire (Stirlingshire), along with an Edward St. Clair, both described as squires. [Note: it seems unlikely this Edward could be William of Dryden’s son because of the date.]

The documentation to confirm the grant of Dryden to William is now lost, however it formed part of the Roslin estate, being less than half a mile north of Roslin castle. ‘William Sanctclar of Dryden’ is a witness in 1444 to a document addressed to William, Earl of Orkney by Robert Earl of Mar and Garrioch and Lord Erskine and, in a much later court case in 1609, William is named as the ‘party contractor’ or original owner in a dispute about the inheritance of Dryden where each previous generation is named. Presumably William was gifted Dryden by either his father or, more likely, his brother Henry.

William married Agnes  on 4 May 1428 when Henry, Bishop of St. Andrews, grants a charter in favour of ‘William St Clare and Agnes his spouse, of third part of sixth part of town of Lasswade and third part of a cottage in said town.‘ On 10 December 1455 another charter is recorded: ‘William Sinclar in favour of Edward Sinclar his son, of 10 acres (7 acres being arable) of land in Pentland.’ On 25 July 1468 a charter confirms a tack by Patrick the then Bishop of St Andrews to ‘Agnes Sinclare, relict of William Sinclare and Edward Sinclare, her son, a fourth and sixth parts of the town of Lasswade, the kirklands of Lasswade, known as Cotslake, and a cottage next to the bridge of Lasswade, for their lifetimes.

Despite source documents to establish certainty, the likelihood that Agnes was a Chisholm is supported by the fact that William’s aunt, Margaret Halyburton was married to Sir Robert Chisholm, the Constable of Urquhart Castle and, not only that, their son, Alexander Chisholm married Margaret de L’Arde, ‘Lady of Erchless’ in Inverness. Margaret was the daughter of Matilda de Strathearn, sister of Earl Henry Sinclair’s mother, Isabella. Agnes Chisholm’s birth is not recorded but that is not unusual for the time.

One further document dated 11 February 1449/50 is a resignation by William and Agnes of ‘sixth part of town of Lasswade in favour of Edward, his second son.‘ Unless this is a mistranslation of the wording in the original document, it seems their eldest son had died by then and although there is no record of his name, it would be logical to guess he may have been named after his grandfather Henry, in the usual Scottish naming pattern.

Nina Cawthorne, February 2020


William Sinclair, 1st of Dryden (c.1385-bef. 25 Jul 1468) m. Agnes (?) Chisholm
Unnamed son ( -bef. 1450)
Alexander ( -aft. 1455) [witness to his father’s charter, Pentland, 1455]
Margaret m. (1) John Ramsay of Corston (Fife), m. (2) Edmund Chisholm, 1st of Cromlix (Perthshire), son of Robert Chisholm of Chisholm (Roxburghshire) and Marion Douglas of Drumlanrig (Dumfriesshire)
Edward, 2nd of Dryden ( -aft. Jul 1496) m. unknown Crichton
William [usher to the chamber of King James IV and later to Queen Margaret Tudor]
Robert ( -bef. 1506)
George ( -aft. 1527), Rector of Aberfoyle (Perthshire)
Master William of Banks of Row ( -c.1513) [ancestor of Sinclair of Banks, Galivmor and Glassingal] m. unnamed 3rd dau. of James Drummond of Coldoch and Ballochard (Perthshire)
Henry of Nether Ardoch and Drumlaw (Perthshire) m. Beatrice Chisholm, dau. of Edmund Chisholm, 1st of Cromlix, and (2nd wife) Janet Drummond of Coldoch
(?)Elizabeth ( -1578) ‘in Nether Ardoch’ m. John McCanquell
Marion, m. bef. 1542 William Stirling of Glassingal and Dachlewne
Mr Hector, natural son, procurator and prebendary at Seton Collegiate College ( -aft. 1554)
Patrick ( -c.1545), natural son, of Spotts (Kircudbrightshire) and Woodhouselee (Midlothian), m. (1) bef. 1509 Margaret Gordon, dau. of John Gordon of Lochinvar (Dumfriesshire). m. (2) aft. 1513 Elizabeth Stewart, widow of Mungo Home of Coldenknowes
John ( -c.1564), natural son, m. Isobel Hamilton, dau. of James Hamilton of Innerwick and Helen Home of Coldenknowes
Isobel Sinclair m. James Hamilton of Boswellhaugh
Alison Hamilton m. Gavin Hamilton, Bishop of Galloway
Alison Sinclair m. David Hamilton of Monktown Mains
David Hamilton
James Hamilton
Andrew Hamilton
Sir John, 3rd of Dryden (c.1455-1535) [courtier and ambassador for King James IV] m. Katherine, dau of William Ramsay of Polton
John ( -bef. 31 Jan 1532) m. Beatrice, dau. of John Folkert of Folkerton (Lanarkshire)
Edward ( -1549) m. Helen Greenlaw
William ( -c.1579) m. Agnes Bothwell, dau. of Francis Bothwell and Katherine Bellenden [Katherine m. (2) Sir Oliver Sinclair of Pitcairns]
Francis Sinclair ( -aft.1598)
Helen m. John Lowis of Mener (Peebleshire)
Edward, 4th of Dryden ( -c.1559) m. (1) Margaret, dau. of David Ramsay of Bangour (Linlithgowshire)
Marion ( -aft. 1564) m. John Henderson (1524- ) son of George Henderson, 2nd of Fordell (Fife) and Katherine Adamson
James Henderson [‘apparent of Dryden’, 1588]
m. (2) bef. Sep 1529 Janet Henryson ( -aft. 1536)
Helen ( -Jul 1569) m. Dr Edward Henryson (c.1522-c.1590), advocate [Dr. Edward Henryson m. (2) Helen Swinton]
Elizabeth Henryson m. John Nicolson, advocate [who acquired Lasswade, Dryden and Pentland in 1591]
(?)Margaret Sinclair m. (1) John Sinclair of Herdmanston ( -1566)
Sir William St. Clair ( -1594) of Herdmanston, m. Sybil Cockburn of Ormiston (East Lothian)
John St. Clair
Oliver St. Clair
Alexander St. Clair
Beatrice St. Clair
Margaret St. Clair
Jane St. Clair
m. (2) 1567 Sir James, ‘the Black Laird’ of Ormiston (1522-1573) [murderer of Henry Stuart, Lord Darnley, hung for treason, 1573] no issue
m. (3) c.1537 Beatrice Renton, dau. of David Renton of Billie (Berwickshire) [widow of William Sinclair of Herdmanston ( -1530), divorced from William Crichton of Drylaw 1536 on the grounds of adultery with his brother, James]
John, 5th of Dryden, m. 1557 Catherine Crichton, dau. of Patrick Crichton of Lugton (Midlothian)
John, 6th of Dryden, m. 1584 Margaret Gifford, dau of James Gifford of Sheriffhall (Midlothian)
John, ‘sometime of Dryden’ [charged with assaulting a servant at his house in Dalkeith (Midlothian), 1600]
James ( -aft.1587) [caution for James Gifford, younger of Sherrifhall, 1587]


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