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The Bowles of Monmouthshire, Wales

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The Norman English occupied Wales in 1070 but they held it for many years by force of arms against a constant threat from the Welsh.  Their stronghold was at Chepstow Castle which was held by a succession of Earls whose knights occupied smaller castles in the surrounding areas to maintain local order and to give early warning of any Welsh uprising.
The Bowles first appear on record in this area in 1382 when Sir Thomas Bowles, Knight is mentioned as a jurist at an inquisition at Magor.  At that time he was of Porth Sgiwed (Portskewett near Caldicot) which doesn't seem to have been the site of a castle.  That would imply that at that time he was a knight of nearby Caldicot Castle which at that time was held by King Richard II's uncle Thomas of Woodstock.  Being a knight in this period wasn't just an honorary title.  In the 1380's the defences of Caldicot were strengthened including the addition of a new gatehouse and drawbridge

This story actually begins with the St Maur family who held Penhow Castle for the Earl at Chepstow Castle from at least 1129.  ref.  ref.  By 1382 the younger lines of the St Maur family had moved on to Wiltshire (there are also definite linkages between these Bowles in Monmouthshire and The Bowles of Wiltshire) where they would become the powerful Seymour family.  The senior line at Penhow found itself with no male heir but the lone daughter, Isabella Seymour, had married John Bowles bringing with her Penhow Castle and a vast increase in the family's fortunes.  At that time Chepstow Castle was held by Margaret, Duchess of Norfolk, daughter and sole heir of Thomas of Brotherton, 1st Earl of Norfolk and the eldest son of King Edward I.  

Excerpt from the Penhow Castle page on the Castles of Wales page:
The Bowles of Penhow adopted the arms of the Seymour family, the simple paired wings of the hunting lure, and in 1438 Thomas Bowles, John's grandson, led a small force of men from Penhow all the way to Berwick-upon-Tweed on the Scottish border to assist in the siege of the town. The siege was part of the complicated politics of the War of the Roses. For his services, Thomas Bowels was knighted by the Duke of Gloucester and returned to Penhow with a substantial pension. He then married Maud, daughter of Sir Thomas Morgan of nearby Pencoed Castle. His arms, the paired wings, and hers, the griffin or dragon of the Morgans, are carved in stone on the outside of one of the windows of the great hall. Sir Thomas's son produced an only daughter, Maria, who married Sir George Somerset, brother of the 2nd earl of Worcester, Lord of Raglan Castle.
This grand estate in Wales then passed out of the Bowles family. ref.  However, the younger male lines continue on in the area even today.  The Bowles spelling actually became common only in later years.  In these earlier records Bouliers, Bowlays, Bollys etc. are seen.
One of the consistent themes here is that these Bowles were knights of royal households.

Some Speculation

I prefer evidence to speculation but there is so little transcribed matter available for this period and from central Canada here I have no chance to do the research with the original documents in the archives of Britain and Wales so the following possibility may never be considered unless I allow myself some speculation here.
In the 1200's two de Buelles brothers held very high positions as household knights of Henry III.  They were likely members of the de Buelles family of Bedfordshire who are believed to have been descendants of knights from the village of Bouelles in Normandy, who had accompanied their Lord Hugh de Gournay,  one of the most powerful Lords under William the Conqueror in his invasion of England in 1066 and who I believe were ancestors of many of today's Bowles. 
In 1233 Henry III appointed his knight William de Boeles to have the custody and the income of the castles of Montgomery and Sneath on the Welsh border.  Montgomery Castle was one of the line of castles which started with Chepstow Castle and ran along the Welsh Marches, a disputed area along the Wales/England border.  The Welsh Lord Llewellyn the Great did attack the this line of defences in 1233 but had to withdraw.  In 1241 Hugh de Boelles (William's brother) appears in the close and pipe rolls as serving the King in Wales.  In 1257 a Richard de Bueles was guaranteed protection of his lands while he was on the King’s son Edward’s service in Wales.  A John Bole was holding Camrose Castle in Pembrokeshire, Wales in 1287 (Bole is from a later transcription and likely not the original spelling of the name).  He was possibly the same knight for whom a Letter of Respite of Debts was issued to the Sheriff of Bedfordshire for a John de Boeles when he set out for Scotland with King Edward I‘s army, in 1300 a John de Boeles was one of Hugh le Despenser's knights and in 1303 one of the same name served with the Prince of Wales and in 1308 is mentioned as being of Gravenhurst, Bedfordshire. 
They usually appear with the surnames as spelled above but sometimes as Bowles probably due to transcribers trying to be overly helpful by modernizing the names in the old documents for the benefit of modern researchers.  With a military tradition at such a high level the de Boeles of Bedfordshire family would be a likely source for Sir Thomas Bowles of Portskewett another knight of the royal household.

The Bowles of Penhow Family Tree

Sir Thomas Bowles, Knight of Porth Sqiwed b. ~ 1330 d. aft. 1382
1.        John Bowles, Lord of Porth Sgiwed (Portskewett near Caldicot) b. ~ 1370 d. aft 1423
m. Isabella Seymour (b. ~ 1370; father: Roger Seymour (St. Maur))
1.1  Ralph Bowles (of Monmouthshire) b. ~ 1400 d. aft. 1439
m. Joan
1.1.1  Sir Thomas Bowles, Knight of Pen-hw (Penhow) , Monmouthshire b. ~ 1430 d. 1511
(a Baron of the Exchequer)
m. Mawd Morgan (b. ~ 1470; father:  Sir Thomas ap Morgan of Pen-coed, Llanfarthin)  Jane Bowles b. ~ 1470 d. aft. 1511
m.(1) Edmund Vanne of Glamorganshire, Wales
children: William, Thomas, Jane, Alice, Lewys, John, Mary Vanne
m.(2) Lewys ap Thomas
child: Thomas Lewis    Margred Bowles b. ~ 1470
m. John Moore
children: Anne, Richard, Florence Moore    Sir Thomas Bowles, Knight b. ~ 1470 d. aft 1511
m.(1) Alice Wogan (Henry) of Prendergast, Pembrokeshire, Wales
m.(2) Jane Vaughan of Monmouthshire  Mawd (Maria) Bowles b. ~ 1500 of Pen-hw, Monmouthshire
m. Sir George Somerset, Knight    Joan (Jane the younger) Bowles b. ~ 1500 d. aft. 1562
m. Sir Edward Aston, Knight of Tixall, co. Staffordshire  Giles Aston (must have d. young)  Sir Walter Aston b. Oct. 8, 1530 Tixall, co. Staffordshire (son and heir)
m. Elizabeth Leveson bef. Apr. 8, 1545 (James, a London merchant; Margaret Offley of Chester)  Sir Edward Aston of Tixall, co. Staff. and Wanlip, co. Leicester
m. Anne Lucy (Sir Thomas of Charlecote, co. Warwick) (MP for Staffordshire 1553, knighted by Duke of Norfolk after the Siege of Leith, Sheriff of Staffordshire 1570-71, 1580-81)  Sir Walter Aston (1st Lord Aston of Forfar)  Edward Aston of the Jewel Office m. Anne Sadleir  Thomas Aston of the Inner Temple  Joyce Aston m. Sir Martin Culpepper of Deane, co. Oxford
Sir Edward d. Apr. 2, 1589  several more children (Cracrofts Peerage: Aston of Forfar)  Leonard Aston  Anthony Aston  Katherine Aston m. Sir William Gesley  Mary Aston m. Sir Simon Harcourt  Anne Aston  Frances Needham Aston
Joan d. Sept. 22, 1562
Sir Edward d. ~ 1568  Walter Bowles of Matharn, Monmouthshire b. ~ 1500
m. ?
(Walter Boules of Westfield, Pembrokeshire in 1536 ref)  Margred (Margaret) Bowles b. ~ 1526
m. Roger Martin of Long Melford, Suffolk
Roger bur. Apr. 16, 1578 Long Melford
Margred bur. Aug. 7, 1615  possibly Thomas Bowles (Lewis Bowles mentions his nephew Thomas Bowles in his Will; if a full nephew, he would only fit here)
Walter d. aft. 1535  Lewys Bowles b. ~ 1500
m. (1) ?
m. (2) Elsbeth (Elizabeth) Bowen of Fishweir, Sain Hilari, Glamorganshire, Wales  Thomas Bowles (of Pen-hw and Middle Temple, London) b. ~ 1545 d. 1580
(Will dated Aug. 27, 1580; proven Feb. 1, 1581; no children mentioned)  Catrin Bowles b. ~ 1530 d. aft. 1580  Margred Bowles b. ~ 1530 m. Haberdeyn d. aft. 1580  Jane Bowles b. ~ 1530 d. aft. 1580
m. Edmond Maddock of Todenham, Glos., Gent.
children: Angelina, Catherine, Hester
Lewis d. 1552 (Will dated Jan. 18, 1551, Proven May 2, 1552) text
(note: his Will refers to a nephew Thomas Bowles but otherwise we have no record of him; possibly that was his brother Walter's son as his eldest brother Sir Thomas was known to have had no male heir)
Elizabeth m.(2) Richard Batharne ca. 1553
1.  Roger Batharne b. ca. 1555
2.  Anne Batharne
Richard d. bef. 1580  Alice Bowles b. ~ 1500 unm. in 1580 d. aft. 1580
Thomas Bowles d. 1511 (Will dated Oct. 1511, proved Dec. 1511) text
Primary References:
  1. A History of Monmouthshire from the Coming of the Normans into Wales down to the Present Time; Sir Joseph Alfred Bradney ref.
  2. Heraldic Visitations of Wales and Part of the Marches Between the Years 1586 and 1613 by Lewys Dwnn
  3. Welsh Genealogies AD 1400-1500;  Peter Clement Bartrum
  4. Cracrofts Peerage
I haven't done any further research on the Bowles in this area yet.
(note for future research)
1851 Wales Census: Monmouthshire, Abergavenny, page 367
Robert Bowles, head, age 38, veterinary surgeon, b. Alburgh, Norfolk, England
Elizabeth Bowles, wife, age 41, Beeston, Norfolk, England
Robert Bowles, son, age 16, dispenser of medicine, b. Norwich, Norfolk, England
Augustus Bowles, son, age 14, b. Blaenavon, Monmouthshire, Wales
Maria Bowles, daughter, age 12, , b. Blaenavon, Monmouthshire, Wales
Elizabeth Bowles, daughter, age 10, b. Blaenavon, Monmouthshire, Wales
William W. Bowles, son, age 2, b. Abergavenny, Monmouthshire, Wales

This site was last updated 12/21/19