In searching for Henry Pennington of Virginia, it may be prudent to concentrate on the ‘main trunk’ of this family rather than its outlying ‘yeoman’ branches, which, by deduction, was likely to have stemmed from a younger brother of William Pennington, 1517-1571, sheriff of Cumberland, as follows, and which spread to the likes of Coulton and Furness fells in the lordship of Furness.

In one sense, the identity of Henry Pennington of Virginia is as unlikely to be discovered as that of his son-in-law, George Trewitt (Tyrwhitt); yet, if families of Pennington and Tyrwhitt can be found in England to have been closely connected, then these connections almost certainly are the ones repeated in Virginia – the ‘continuation of associations’ being the 24 carat hallmark of the English kinship system.

1. Sir Alan de Pennington (d.1415) m. Katharine de Preston, dau of Sir Richard de Preston, who held land in Furness Fells. ‘Inquisition taken at Lancaster after the death of Alan de Penyngton, who held the manor of Pennington of the abbot of Furness, John de Pennington being his son and next heir’ (Annual Report by the Deputy Keeper of the Public Records, vol. 36).
1.1. Sir John Pennington (1393-1470), m. (1413) Katharine, dau of Sir Thomas de Tunstall and Isabel, dau. of Sir Nicholas Harrington (who also held land in Furness Fells), and sister of Sir William Harrington, husband of Margaret Nevill, dau. of Robert de Nevill, Sheriff of Yorkshire.
1.1.1. Ann Pennington, m. Christopher Curwen, son of ‘Sir Christopher Curwen, s. and h. of Sir William Curwen by his 1st w. Ellen. m. Elizabeth (d. aft. 1468), da. of Sir John Huddlestone of Millom castle’ (The History of Parliament: the House of Commons 1386-1421, ed. J.S. Roskell, L. Clark, C. Rawcliffe., 1993).
1.1.2. John Pennington, heir to his grandfather, by inquis. 1503, sheriff of Cumberland in 1510, m. Elizabeth, dau. of Sir Nicholas Radcliffe, of Derwentwater, sheriff, Cumberland, 1422/3, 1426/7.
1.1.2.1. Sir John Pennington of Muncaster, Sheriff of Cumberland, d. 1512, m. (1) Isabel, dau. of John Broughton, (2) Joan, dau. of Sir William Eure of Witton Castle and Maud, dau. of Lord FitzHugh of Ravenswath Castle. ‘Grant by Nicholas Radclyff, knt., John Knobilhowe, parson of the church of Lamplugh, William Farlam and Robert Roskyll, chaplain, to John son of John Penyngton, esq., and to Isabel his wife, daughter of John Broghton, esq., of a yearly rent after the death of John Penyngton, knt., in Preston in Kendale’. Dated August 12, 1452. (Hist. MSS. Com., Rep. x, app. iv., p. 225).
1.1.2.1.1. John Pennington of Muncaster (d. 1516), m. Mary dau of Sir John Hudleston, ‘on which marriage in the 23rd Edward IV. the estate was settled upon the issue male. And he having only a dau. Isabel, married to Thomas Dykes, of Warthole, Esquire, the estate came to the second brother, William Pennington, Esq., who was succeeded by Joseph Pennington, Esq., son and heir. Sir William Pennington, knight, son and heir, m. Isabel, dau. of John Farrington, of Warden, in Lancashire, Esq., with whom he had the manor of Farrington. On an inquisition of knights’ fees in Cumberland, in the 35th Henry VIII., it is found that this Sir William held the manor of Muncaster of the king as of his castle of Egremont, by the service of the sixth part of one knight’s fee (Samuel Jefferson The History and Antiquities of Allerdale Ward, Above Derwent, in the County of Cumberland, p. 229, 1842).

(1. John Nevill, Earl of Northumberland.
1.1. Lucy Nevill, m. Sir Thomas FitzWilliam, of Aldwark.
1.1.1. Thomas FitzWilliam, m. Ann, dau. of Sir Nicholas Pagenham.
1.1.1.1. Alice FitzWilliam, m. Sir James Foljambe.
1.1.1.1.1. Godfrey Foljambe, m. Troth Tyrwhit, dau of Sir William Tyrwhit, of Kettleby and Elizabeth, da. and h. of Sir Thomas Oxenbridge of Etchingham, Suss.; and sister of Tristram Tyrwhit, who m. Alice, da. of Sir William Skipwith of Ormsby, Lincs; the sister of Margaret Skipwith, who m. John Trye of Hardwicke (1540 – 1591). Tristram Tyrwhit, ‘b. c. 1530, s. of Sir William Tyrwhitt (d.1541), of Scotter, Lincs. (sheriff, Lincs. 1537) by Isabel, da. of William Girlington of Normanby, wid. of Christopher Kelke; bro. of Marmaduke and Sir Robert.
Robert Tyrwhitt, d. 1581, was the father of George Tyrwhitt, born ca. 1562. I suggest that George Truitt Sr. (Tyrwhitt) of Virginia was of this line.
1.2. Isabell Nevill, m. William Huddleston; she m. 2. Sir William Smythe, Escheator of Lancashire, Sheriff of Staffordshire, having issue : George Smith alias Harris. William Huddleston was the bro. of (1) John Huddleston and (2) Mary Pennington (wife of Sir John Pennington). John Huddleston was the father of John Huddleston, who m. (1) Joyce Prickley, by whom he had issue: Bridget Huddleston, who m. William Pennington of Muncaster, Sheriff of Cumberland (1517-1573).
1.2.1. Sir John Huddleston, m. Elizabeth, dau. of Edward Sutton, and sister of Joyce Leighton, wife of John Leighton, of Wattlesborough. (DDMC 6/11).

1.1.2.1.1.1. Isabel Pennington, b. 1485, m. Thomas Dykes.
1.1.2.1.2. Alan Pennington.
1.1.2.1.3. William Pennington of Newton (d. 1513), m. (1488) Anne, dau. of George Martindale, of Carlisle.
1.1.2.1.3.1. John Pennington, heir male to his uncle, b. 1497, d. 1522; inquis. 1527.
1.1.2.1.4. Elizabeth Pennington, m. (2., in 1491), Sir Walter Strickland.
1.1.2.1.4.1. Agnes Srickland, m. Thomas Curwen.
1.1.2.1.5. Margaret Pennington, m. (1) John Lamplugh, grandson of John Lamplugh (whose maternal uncle was Sir Alan Pennington), s. and h. of Sir John Lamplugh (exec. 8 June 1405), of Lamplugh by his w. Elizabeth, da. and coh. of Sir Richard Preston (d. by 1393) of Preston Richard and Burton, Westmld.

1.1.2.1.2. William Pennington, of Newton, Cumberland.
1.1.2.1.2.1. John Pennington, b.. 1497, heir male to hIs uncle, John; d. 1522.
1.1.2.2. William Pennington, of Hundiston, Herts., d. 1513, member of the King’s household, m. Frances, dau. of Henry Palgrave, and Ann, dau. of John Glemham, of Suffolk, and Eleanor Brandon, dau. of Sir William Brandon, Escheator for Norfolk and Suffolk, Marshall of the King’s Bench, servant of the King’s Household.
1.1.2.2.1. William Pennington, 1517-1571, sheriff of Cumberland (heir male to his cousin, John, son of William Pennington, of Newton), d. seised of the manor of Preston Richard. He m. (1) Joan, dau. of Thomas Wharton, sheriff of Cumberland, and Eleanor, dau. of Sir Brian Stapleton, of Wighill. (2, in 1563) Bridgit (dau. of John Huddleston, and his third wife, Joyce Prickley, dau. of John Prickley, of Prickley, Worcestershire), relict of Hugh Askew/Ayscough (d. 1562); of the same family (probable brother) as Sir William Askew, of Kelsey, Lincolnshire, whose son received lands from Hugh Askew. Sir William Askew was the father of Anne Askew, the Protestant martyr and poet burned in 1546. Her br. Edward Askew/Ayscough m. Margaret, dau. of Thomas Gibson of Cotham, relict of George Skipwith, son of Sir William Skipwith of South Ormsby.

Ann Askew:

“I am not she that list
My anchor to let fall
For every drizzling mist
My ship substancial”.

1.1.2.2.1.1. Joseph Pennington, 1564-1640.
1.1.2.2.1.2. John Pennington, d. 1613. On May 21, 1606, “Dame Bridget Pennington alias Askew of Seaton grants to John Pennington of Seaton, her second son, a yearly rent of £200, which was to be paid to her by her son Joseph Pennington, esquire. William Pennington his son succeeds to the Seaton estates. Dugdale’s Visitation of Cumberland shows William Pennington of Seaton to be aged 70 in 1665. His son was Miles Pennington, sheriff of Cumberland.
1.1.2.2.1.3. William Pennington.

Either John Pennington, d. 1613, or his brother, William, are the most likely fathers of Henry Pennington of Virginia. In this suggestion Henry Pennington’s grandmother would be Bridgit Huddleston, likely sister-in-law of Sir William Askew, and, thus, aunt of Anne Askew and her brother Edward Askew, who m. the relict of George Skipwith (son of Sir William Skipwith of South Ormsby), brother of the wife of Tristram Tyrwhit, whose brother was the father of George Tyrwhitt, born ca. 1562. I suggest that George Truitt Sr. (Tyrwhitt) of Virginia was of this line; perhaps grandson of his namesake.

The points of intersection are very unlikely to be coincidental, and what are unknown and unknowable in a strict sense become ‘known unknowns’, as informed by a knowledge of the English kinship system.

I give the associations of Miles Pennington to stress the central status of continuing intermarriages between the same families:

Wilfrid Lawson m. Jane, dau. of Sir Edward Musgrave, of Hayton, Cumberland. Of Sir Wilfrid’s eight daus., Elizabeth, m. John Stapleton, of Wartre; Judith m. Miles Pennington, of Seaton, Cumberland; Catherine m. Andrew Huddleston, of Hutton-John, Cumberland; Isabel, m. D’arcy Curwen, of Sells-park, Cumberland. William Lawson, Esq; eldest son, m. Milcha, dau. of Sir William Strickland, of Boynton, Yorkshire,by whom he had Sir Wilfrid, his successor, who m. Elizabeth, only dau. and heir of George Preston Esq., of Holker, Lancashire.

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