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Pickerings of Oswaldkirk

A Y-DNA test taken by my nearest male relative currently reveals as many matches with men bearing the name Allen as Pickering and one Dunbar, which can only mean that the families share the same male line. The name Allen derives from a Celtic personal name of great antiquity and obscurity, found in England and Scotland well before the Normans introduced surnames into the British Isles. The branch of the Allen family that gave rise to the Pickerings shortly after the Norman Conquest was also the progenitor of the line that nearly a century earlier adopted the name Dunbar. The history books do not tell us at what point in time a man carrying Allen genes fathered a boy whose family later took the name Pickering, but DNA testing tells us that the family that became the Oswaldkirk Pickerings of England and the family that became the Dunbars of Scotland branched off into two parallel lines in about 150 BC.

The Oswaldkirk family must have risen to prominence at an early date as documentary evidence already exists for them in the 13th century: Adam, the son of the first Thomas, witnessed a charter regarding lands in Cawthorne in about 1200 and his family was holding land in Newton-on-Rawcliffe in the mid 1200s, both places lying on the North York Moors roughly 5 km. north of Pickering.

Documentary evidence shows that the Oswaldkirk Pickerings maintained close ties in the early years with the de Bruses, indicating that they were perhaps related in the female line. Both families had holdings in Pickering and Ryedale and did not hesitate to stand bail for one another and pay each other’s fines, which were imposed during the eyrie held in the 1330s to judge misdemeanours committed in Pickering Forest. Furthermore, the early Oswaldkirk Pickerings gave their sons the very de Brus names of Adam, Robert and William.

The main Oswaldkirk line moved out of Pickering when Richard de Pickering acquired lands in Ryedale through his marriage in c1310 to Joan de Barton, heiress to Oswaldkirk and Ampleforth. Their son Thomas was buried in the church at Oswaldkirk in 1348, but it is only the tomb of Sir Richard Pickering (1431-1432) that survives today in an alcove on the church’s south side. The main line of the family later moved to London, and Oswaldkirk and Ampleforth eventually passed to Sir Edward Wotton through his marriage to Hester, the daughter of the second Sir William Pickering.

The relationship between the main line and the siblings is based on circumstantial evidence.

1st Generation

1. Thomas de PICKERING born c1140, married Unknown UNKNOWN.
Children:
1.1. Adam de PICKERING
1.2. Robert de PICKERING

2nd Generation

1.1. Adam de PICKERING born c1175, married Unknown UNKNOWN.
Children:
1.1.1. John de PICKERING
1.1.2. Thomas de PICKERING
1.1.3. Adam de PICKERING

1.2. Robert de PICKERING clergyman.

3rd Generation

1.1.1. John de PICKERING born c1200, died before 1265.

1.1.2. Thomas de PICKERING born c1205, died before 1252, married Mathilda UNKNOWN.
Children:
1.1.2.1. William de PICKERING
1.1.2.2. James de PICKERING
1.1.2.3. Geoffrey de PICKERING
1.1.2.4. Richard de PICKERING

1.1.3. Adam de PICKERING born c1210, married Unknown UNKNOWN.
Children:
1.1.3.1. Thomas de PICKERING
1.1.3.2. Alice de PICKERING
1.1.3.2. John de PICKERING

4th Generation

1.1.2.1. William de PICKERING born c1230, died before 1314.

1.1.2.2. James de PICKERING miller, born c1235.

1.1.2.3. Geoffrey de PICKERING born c1245, married Unknown UNKNOWN.
Children:
1.1.2.3.1. Hugh de PICKERING

1.1.2.4. Richard de PICKERING born c1250 married Unknown UNKNOWN.
Children:
1.1.2.4.1. Nicholas de PICKERING

1.1.3.1. Thomas de PICKERING keeper of the castle, Athlone, Westmeath, Ireland, born c1230 married Unknown UNKNOWN.
Children:
1.1.3.1.1. William de PICKERING
1.1.3.1.2. Roger de PICKERING

1.1.3.2. Alice de PICKERING.

1.1.3.3. John de PICKERING reeve, Pickering, North Riding, died 1316, married Unknown UNKNOWN.
Children:
1.1.3.3.1. Geoffrey de PICKERING
1.1.3.3.2. Emma de PICKERING

5th Generation

1.1.2.3.1. Hugh de PICKERING.

1.1.2.4.1. Nicholas de PICKERING.

1.1.3.1.1. William de PICKERING born c1260, married Eufamia UNKNOWN.
Children:
1.1.3.1.1.1. Richard de PICKERING
1.1.3.1.1.2. John de PICKERING
1.1.3.1.1.3. Adam de PICKERING
1.1.3.1.1.4. Robert de PICKERING
1.1.3.1.1.5. William de PICKERING
1.1.3.1.1.6. Roger de PICKERING

1.1.3.1.2. Roger de PICKERING clerk.

1.1.3.3.1. Geoffrey de PICKERING

1.1.3.3.2. Emma de PICKERING

6th Generation

1.1.3.1.1.1. Richard de PICKERING landholder Oswaldkirk and Ampleforth, North Riding, born c1280, died 1349, married Joan de BARTON (daughter of Nicholas de BARTON).
Children:
1.1.3.1.1.1.1. Thomas de PICKERING
1.1.3.1.1.1.2. Joan de PICKERING
1.1.3.1.1.1.3. Hugh de PICKERING

1.1.3.1.1.2. John de PICKERING commissioner, landholder Great Habton, North Riding, married Eufamia UNKNOWN.
Children:
1.1.3.1.1.2.1. Eleanor de PICKERING

1.1.3.1.1.3. Adam PICKERING rector of Londesborough, East Riding, master of St. James Hospital, Northallerton, North Riding.

1.1.3.1.1.4. Robert de PICKERING bailiff, landholder Pickering, Farmanby and Great Habton, North Riding, married Unknown UNKNOWN.
Children:
1.1.3.1.1.4.1. John de PICKERING
1.1.3.1.1.4.2. Robert de PICKERING

1.1.3.1.1.5. William de PICKERING.

1.1.3.1.1.6. Roger de PICKERING.

7th Generation

1.1.3.1.1.1.1. Thomas de PICKERING woodward of Pickering forest, landholder Ampleforth and Holme, North Riding, born c1310, died 1348, buried Oswaldkirk, married Margaret MALECAKE (daughter of Alan and Itaria MALECAKE) landholder in Lockton.
Children:
1.1.3.1.1.3.1.1. Richard de PICKERING
1.1.3.1.1.3.1.2. Alice de PICKERING
1.1.3.1.1.3.1.3. Roger de PICKERING
1.1.3.1.1.3.1.4. John de PICKERING
1.1.3.1.1.3.1.5. Geoffrey de PICKERING

1.1.3.1.1.1.2. Hugh de PICKERING priest, master of the Hospital of St. Mary, York, North Riding.

1.1.3.1.1.1.3. Joan de PICKERING nun, prioress of Rosedale Priory, North Riding, 1310.

1.1.3.1.1.2.1. Eleanor de PICKERING married Geoffrey SUETHAND.

1.1.3.1.1.4.1. John de PICKERING rector 1320 church of St. Crux, York, North Riding, prior 1369 St. Augustine’s friars, York.

1.1.3.1.1.4.2. Robert de PICKERING vicar 1349 St. German’s, Winestead, East Riding, rector 1359 St. Oswald’s, Oswaldkirk, North Riding, vicar 1363 All Saints’ Preston, East Riding, chaplain 1391 St. Peter and St. Paul’s, Pickering, North Riding, landholder Great Habton and Pickering, North Riding.

8th Generation

1.1.3.1.1.3.1.1. Richard de PICKERING landholder Oswaldkirk and Lockton, North Riding, born 18 October 1330, married Beatrice DARRELL.
Children:
1.1.3.1.1.3.1.1.1. John de PICKERING

1.1.3.1.1.3.1.2. Alice de PICKERING prioress 1352 Yedingham Priory, East Riding.

1.1.3.1.1.3.1.3. Roger de PICKERING master of St. Mary Magdalene Hospital, Ripon.

1.1.3.1.1.3.1.4. John de PICKERING rector 1384 St. Mary’s Castlegate, York, North Riding, died c1395 York, North Riding.

1.1.3.1.1.3.1.5. Geoffrey de PICKERING abbot c1397-c1400 of Byland Abbey, North Riding, died before 1417.

9th Generation

1.1.3.1.1.3.1.1.1. John de PICKERING landholder Oswaldkirk, Ampleforth and South Holme, North Riding, born c1350, married c1370 Unknown UNKNOWN.
Children:
1.1.3.1.1.3.1.1.1.1. Roger PICKERING

10th Generation

1.1.3.1.1.3.1.1.1.1. Roger PICKERING born c1370, married Margaret UNKNOWN.
Children:
1.1.3.1.1.3.1.1.1.1.1. Sir Richard PICKERING
1.1.3.1.1.3.1.1.1.1.2. Joan de PICKERING
1.1.3.1.1.3.1.1.1.1.3. John de PICKERING
1.1.3.1.1.3.1.1.1.1.4. Robert de PICKERING
1.1.3.1.1.3.1.1.1.1.5. Hugh de PICKERING
1.1.3.1.1.3.1.1.1.1.6. Edmund de PICKERING
1.1.3.1.1.3.1.1.1.1.7. Matilda de PICKERING
1.1.3.1.1.3.1.1.1.1.8. Marjory de PICKERING

11th Generation

1.1.3.1.1.3.1.1.1.1.1. Sir Richard PICKERING knight, 1431-1432 sheriff of Yorkshire, commissioner of the peace for Yorkshire, landholder Rydale and North Riding, born c1390, died 11 September 1441, buried in St. Oswald’s, Oswaldkirk, North Riding, married Margaret HILDYARD.
Children:
1.1.3.1.1.3.1.1.1.1.1.1. Sir John PICKERING
1.1.3.1.1.3.1.1.1.1.1.2. Thomas PICKERING

Pickering of Oswaldkirk arms
Sir Richard Pickering's arms
Sir Richard Pickering
Sir Richard Pickering
Tomb of Sir Richard Pickering
tomb of Sir Richard Pickering
St. Oswald's, south side of nave
Nave of St. Oswald's church
nave of St. Oswald's, 2016

1.1.3.1.1.3.1.1.1.1.2. Joan de PICKERING nun, Nun Monkton nunnery, West Riding.

1.1.3.1.1.3.1.1.1.1.3. John de PICKERING controller of Calais, landholder Oswaldkirk and Ampleforth, North Riding, died before 1437, married Cecily UNKNOWN.
Children:
1.1.3.1.1.3.1.1.1.1.3.1. Elizabeth de PICKERING

1.1.3.1.1.3.1.1.1.1.4. Robert de PICKERING gentleman, Oswaldkirk, North Riding.

1.1.3.1.1.3.1.1.1.1.5. Hugh de PICKERING.

1.1.3.1.1.3.1.1.1.1.6. Edmund de PICKERING.

1.1.3.1.1.3.1.1.1.1.7. Matilda de PICKERING married John DILCOCK.

1.1.3.1.1.3.1.1.1.1.8. Marjory de PICKERING married Unknown HORSMAN.

12th Generation

1.1.3.1.1.3.1.1.1.1.1.1. Sir John PICKERING governor of English merchants, Flanders, commissioner of the peace, landholder Oswaldkirk, Ampleforth, Pickering and Lockton, North Riding, born c1430, died before 1510, married 1st Joan GREEN (daughter of Sir Thomas GREEN and Marina BELLERS) born in Greens Norton, Northamptonshire, died before 1470, married 2nd Margaret EGREMONT (daughter of Thomas PERCY) died Elmswell, East Riding.
Children of Sir John PICKERING and Joan GREEN:
1.1.3.1.1.3.1.1.1.1.1.1.1. Thomas PICKERING
1.1.3.1.1.3.1.1.1.1.1.1.2. Elizabeth PICKERING
1.1.3.1.1.3.1.1.1.1.1.1.3. Eleanor PICKERING
1.1.3.1.1.3.1.1.1.1.1.1.4. Hugh PICKERING
Children of Sir John PICKERING and Margaret EGREMONT:
1.1.3.1.1.3.1.1.1.1.1.1.5. Margaret PICKERING

1.1.3.1.1.3.1.1.1.1.1.2. Thomas PICKERING abbot of Whitby Abbey, genealogist, died 1475 Whitby, North Riding.

1.1.3.1.1.3.1.1.1.1.3.1. Elizabeth de PICKERING landholder Scalby, Barmston, Arnold and Long Riston, East Riding.

13th Generation

1.1.3.1.1.3.1.1.1.1.1.1.1. Thomas PICKERING esquire, landholder Oswaldkirk, Ampleforth, Pickering and Lockton, North Riding, and Cherry Burton, East Riding, born c1450 died 1509, buried Greyfriars’ Newgate, London, married Joan FITZWILLIAM (daughter of Sir Thomas FITZWILLIAM of Mablethorpe and Margaret HARINGTON), had children with Jane UNKNOWN, servant.
Children of Thomas PICKERING and Joan FITZWILLIAM:
1.1.3.1.1.3.1.1.1.1.1.1.1.1. Sir William PICKERING
1.1.3.1.1.3.1.1.1.1.1.1.1.2. John PICKERING
1.1.3.1.1.3.1.1.1.1.1.1.1.3. Margaret PICKERING
1.1.3.1.1.3.1.1.1.1.1.1.1.4. Thomas PICKERING
1.1.3.1.1.3.1.1.1.1.1.1.1.5. Unknown PICKERING
Children of Thomas PICKERING and Jane PICKERING
1.1.3.1.1.3.1.1.1.1.1.1.1.6. Anthony PICKERING
1.1.3.1.1.3.1.1.1.1.1.1.1.7. Unknown PICKERING

Grey Friars within Newgate, early 16th century
before the Great Fire, 1666
Wren's reconstruction
Wren's church
before the Blitz, 1940
before the Blitz, 1940
Greyfriars today

1.1.3.1.1.3.1.1.1.1.1.1.2. Elizabeth PICKERING married 1st Francis HASTINGS (son of Sir Roger HASTINGS), married 2nd John FITZWILLIAM (son of Sir Thomas FITZWILLIAM and Margaret HARINGTON).

1.1.3.1.1.3.1.1.1.1.1.1.3. Eleanor PICKERING married 1st 1480 Well, North Riding, Richard MIDDLETON, master of Duke of Gloucester’s household, married 2nd William BOROUGH.

1.1.3.1.1.3.1.1.1.1.1.1.4. Hugh PICKERING granted 1485 Park (now Gaynes) Hall, Essex, buried Oswaldkirk, North Riding, married Margaret UNKNOWN, buried Oswaldkirk, North Riding.

1.1.3.1.1.3.1.1.1.1.1.1.5. Margaret PICKERING married 1st John BARTON (son of Christopher BARTON and Margaret DANBY), married 2nd before 1536 Robert ROOS.

14th Generation

1.1.3.1.1.3.1.1.1.1.1.1.1.1. Sir William PICKERING knight marshal to Henry VIII, settled and sold holdings Yorkshire, granted lands of dissolved monasteries Yorkshire and Denbighshire, born c1475, died 1542 Pickering House, St. Mary Street (now St. Mary Mary Axe), Aldgate, London, reburied St. Helen’s Bishopgate, London, married c1510 Eleanor FAIRFAX (daughter of Sir William FAIRFAX) buried 27 June 1563 Oswaldkirk, North Riding, had a child with Unknown UNKNOWN.
Children of Sir William PICKERING and Eleanor FAIRFAX:
1.1.3.1.1.3.1.1.1.1.1.1.1.1.1. Sir William PICKERING
1.1.3.1.1.3.1.1.1.1.1.1.1.1.2. Ann PICKERING
1.1.3.1.1.3.1.1.1.1.1.1.1.1.3. Unknown PICKERING
Children of Sir William PICKERING and Unknown UNKNOWN:
1.1.3.1.1.3.1.1.1.1.1.1.1.1.4. George PICKERING

Pickering House, 1561
Agas Map of London
area of Pickering House, 1666
(after the Fire), British Library
area of Pickering House, 1720
John Stow
site of Pickering House: no. 9?
H.M. Land Registry, 1992
area of Pickering House, 2016

epitaph of Sir William Pickering, father and son

1.1.3.1.1.3.1.1.1.1.1.1.1.2. John PICKERING gentleman, commissioner of array, born c1480, died 1521, married c1500 Jane PERCEHAY (daughter of Lyon PERCEHAY).
Children:
1.1.3.1.1.3.1.1.1.1.1.1.1.2.1. John PICKERING
1.1.3.1.1.3.1.1.1.1.1.1.1.2.2. Anthony PICKERING
1.1.3.1.1.3.1.1.1.1.1.1.1.2.3. Agnes PICKERING

1.1.3.1.1.3.1.1.1.1.1.1.1.3. Margaret PICKERING married Robert TENANT clerk

1.1.3.1.1.3.1.1.1.1.1.1.4. Thomas PICKERING steward of Dame Maude Parr’s household, married Alice GOLDING (daughter of Sir John GOLDING).

1.1.3.1.1.3 1.1.1.1.1.1.1.5. Daughter PICKERING.

1.1.3.1.1.3.1.1.1.1.1.1.1.6. Anthony PICKERING attorney, Calais, France, member of the Calais Constabulary, died before 1542.

1.1.3.1.1.3.1.1.1.1.1.1.1.7. Unknown PICKERING possible second child born after 1509.

15th Generation

1.1.3.1.1.3.1.1.1.1.1.1.1.1.1. Sir William PICKERING knight, ambassador to France, settled and sold holdings Yorkshire and Denbighshire, born 1517 died 4 January 1575 Pickering House, St. Mary Street (now St. Mary Mary Axe), Aldgate, London, buried St. Helen’s Bishopgate, London, had a child with Unknown UNKNOWN.
Children:
1.1.3.1.1.3.1.1.1.1.1.1.1.1.1.1. Hester PICKERING

Byland Abbey, 2016 and 2022

St. Helen’s Bishopgate, City of London

Sir William's tomb
photo: David Babington-Smith
Sir William's effigy
Sir William Pickering's effigy
photo: SilverTiger
Sir William's arms
St. Helen's then
St. Helen's Bishopsgate then
St. Helen's now
St. Helen's Bishopsgate now

1.1.3.1.1.3.1.1.1.1.1.1.1.1.2. Ann PICKERING born c1530 married 20 August 1556 Oswaldkirk, North Riding Roger DELARYVER.

1.1.3.1.1.3.1.1.1.1.1.1.1.1.3. Unknown PICKERING born c1540, married 1562 Thomas DALTON.

1.1.3.1.1.3.1.1.1.1.1.1.1.1.4. George PICKERING born c1540, married Unknown UNKNOWN.
Children:
1.1.3.1.1.3.1.1.1.1.1.1.1.1.4.1. Unknown PICKERING

see Pickerings of Cawton

1.1.3.1.1.3.1.1.1.1.1.1.1.2.1. John PICKERING gentleman, born c1500, buried February 1565 Bishop Burton, East Riding, married c1520 Joan UNKNOWN died October 1565 Bishop Burton, East Riding.
Children:
1.1.3.1.1.3.1.1.1.1.1.1.1.2.1.1. Robert PICKERING
1.1.3.1.1.3.1.1.1.1.1.1.1.2.1.2. Thomas PICKERING
1.1.3.1.1.3.1.1.1.1.1.1.1.2.1.3. Hugh PICKERING
1.1.3.1.1.3.1.1.1.1.1.1.1.2.1.4. John PICKERING

see Pickerings of Holderness

Hester Pickering c1580 portrait and detail
Hester Pickering c1580
detail of portrait (right)
Hester Pickering c1580
courtesy of Ashmolean Museum
of Art and Archaeology, Oxford

1.1.3.1.1.3.1.1.1.1.1.1.1.2.2. Anthony PICKERING gentleman, clerk, born c1520, buried 8 July 1592 in Threekingham, Lincolnshire, married Joan GOWER (daughter of Sir John GOWER and Elizabeth GOLDSBOROUGH, widow of Hugh CLITHEROE).
Children:
1.1.3.1.1.3.1.1.1.1.1.1.1.2.2.1. John PICKERING
1.1.3.1.1.3.1.1.1.1.1.1.1.2.2.2. Thomas PICKERING

1.1.3.1.1.3.1.1.1.1.1.1.1.2.3. Agnes PICKERING born c1525, died 1580 Threekingham, Lincolnshire.

see Pickerings of Threekingham

16th Generation

1.1.3.1.1.3.1.1.1.1.1.1.1.1.1.1. Hester PICKERING holder of Oswaldkirk and Ampleforth, North Riding, and Valle Crucis, Denbighshire, died 8 May 1592 Pickering House, St. Mary Street (now St. Mary Mary Axe), Aldgate, London, married 1 September 1575 Boughton Malherbe, Kent Sir Edward WOTTON (son of Thomas WOTTON and Elizabeth RUDSTON) knight, baronet, comptroller of the household of Queen Elizabeth and James I, ambassador to Portugal, born 1548 Boughton Malherbe, Kent, died 1628 Boughton Malherbe, Kent.

Valle Crucis Abbey, 2023

Sources:
Historical Works of Simeon of Durham, vol. 3, Simeon’s Account of the Siege of Durham, pp.765-768
: https://archive.org/details/historicalworks00simegoog/page/n359
Marriage and Murder in Eleventh-century Northumbria: A Study of ‘De Obsessione Dunelmi’: https://books.google.fr/books/about/Marriage_and_Murder_in_Eleventh_century.html?id=Crnv8jaK7hkC
Bloodfeud: Murder and Revenge in Anglo-Saxon England: https://books.google.fr/books?id=Mz7k0NeveBYC&pg and https://archive.org/details/bloodfeudmurderr0000flet_s2h2/page/n8
Prosopography of Anglo-Saxon England: https://pase.ac.uk/jsp/index.jsp
(Pickering:) The Evolution of an English Town, pp.90-92 (not online)
Early Yorkshire Charters, vol. 2, pp.505-526: Greystoke Fee: https://archive.org/details/earlyyorkshirech02farruoft/page/506
The Honor and Forest of Pickering, vols. 2, 3 and 4:
https://archive.org/stream/honorforestofpic02turt
https://archive.org/details/honorforestofpic03turt
https://archive.org/details/honorforestofpic04turt
Allen Name Meaning: https://www.ancestry.com/name-origin?surname=allen
FTDNA Surname Projects: https://www.familytreedna.com/group-project