Pickerings of Oswaldkirk

It seems likely that the Pickerings of Oswaldkirk emerged from the de Brus family. The first known member, Thomas de Pickering, was a contemporary of William de Brus, the younger son of Adam I, who Dr. Blakely thinks may have given rise to the Pickerings of Killington (see Origins). The de Bruses and the Pickerings of Oswaldkirk maintained close ties through their land holdings and shared the same lion rampant azure arms before the Pickerings adopted the gules chevron argent of Sir Richard and later the gules chevron or of Sir William.

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

de Brus of Skelton and Annandale

de Brus of Skelton and Annandale, adapted from The Brus Family in England and Scotland, 1100-c1290 by Dr. Ruth M. Blakely

early arms

later arms

later arms

Oswaldkirk  Pickerings final arms

final arms

1st Generation

1. Thomas de PICKERING born before 1200, married Unknown UNKNOWN.
Children:
1.1. Adam de PICKERING

2nd Generation

1.1. Adam de PICKERING born before 1200 married Unknown UNKNOWN.
Children:
1.1.1. Adam de PICKERING
1.1.2. Unknown de PICKERING
1.1.3. John de PICKERING

3rd Generation

1.1.1. Adam de PICKERING died after 1314, married Maud UNKNOWN.
Children:
1.1.1.1. John de PICKERING
1.1.1.2. Thomas de PICKERING

1.1.2. Unknown de PICKERING married Mathilda UNKNOWN died after 1252.
Children:
1.1.2.1. William de PICKERING
1.1.2.2. Geoffrey de PICKERING
1.1.2.3. James de PICKERING
1.1.2.4. Adam de PICKERING

1.1.3. John de PICKERING monk, living 1251.

4th Generation

1.1.1.1. John de PICKERING died after 1265 childless.

1.1.1.2. Thomas de PICKERING died after brother John, married Unknown UNKNOWN.
Children:
1.1.1.2.1. William de PICKERING

1.1.2.1. William de PICKERING died after 1314.

1.1.2.2. Geoffrey de PICKERING died after 1293 married Unknown UNKNOWN.
Children:
1.1.2.2.1. Hugh de PICKERING

1.1.2.3. James de PICKERING died after 1295.

1.1.2.4. Adam de PICKERING tax collector Whitby and Scarborough, living 1317, married Maud UNKNOWN.

5th Generation

1.1.1.2.1. William de PICKERING died after 1337, married Unknown UNKNOWN.
Children:
1.1.1.2.1.1. Richard de PICKERING
1.1.1.2.1.2. Robert de PICKERING
1.1.1.2.1.3. John de PICKERING
1.1.1.2.1.4. Adam de PICKERING
1.1.1.2.1.5. William de PICKERING

1.1.2.2.1. Hugh de PICKERING died after 1312.

6th Generation

1.1.1.2.1.1. Richard de PICKERING died 1349, married Joan of BARTON (daughter of Nicholas of BARTON).
Children:
1.1.1.2.1.1.1. Thomas de PICKERING
1.1.1.2.1.1.2. Hugh de PICKERING
1.1.1.2.1.1.3. Joan de PICKERING
1.1.1.2.1.1.4. Nicholas de PICKERING

1.1.1.2.1.2. Robert de PICKERING died before 1409, married Unknown UNKNOWN.
Children:
1.1.1.2.1.2.1. Robert de PICKERING
1.1.1.2.1.2.2. John de PICKERING

1.1.1.2.1.3. John de PICKERING died after 1415, married Eufamia UNKNOWN.
Children:
1.1.1.2.1.3.1. Eleanor de PICKERING

1.1.1.2.1.4. Adam de PICKERING master of St. James’s Hospital, Northallerton, North Riding, died after 1347.

1.1.1.2.1.5. William de PICKERING.

7th Generation

1.1.1.2.1.1.1. Thomas de PICKERING born c1310, died c1348, married Margaret MALECAKE (daughter of Alan MALECAKE) died c1379 Ampleforth, North Riding.
Children:
1.1.1.2.1.1.1.1. Richard de PICKERING
1.1.1.2.1.1.1.2. Roger de PICKERING
1.1.1.2.1.1.1.3. Alice de PICKERING
1.1.1.2.1.1.1.4. John de PICKERING

1.1.1.2.1.1.2. Hugh de PICKERING priest, master of the Hospital of St. Mary, Bootham, York, died after 1331.

1.1.1.2.1.1.3. Joan de PICKERING nun at Rosedale Priory, prioress of Keldholme Priory.

1.1.1.2.1.1.4. Nicholas de PICKERING died after 1322.

1.1.1.2.1.2.1. Robert de PICKERING vicar at Winestead, East Riding, rector at Oswaldkirk, North Riding, vicar at Preston, East Riding, chaplain, died after 1403.

1.1.1.2.1.2.2. John de PICKERING chaplain, parson of a moiety of the church of St. Mary, Castlegate, York, rector of the church of St. Mary, died c1394.

1.1.1.2.1.3.1. Eleanor de PICKERING married Geoffrey SUETHAND.

8th Generation

1.1.1.2.1.1.1.1. Richard de PICKERING born 18 October 1330, died after 1374, married Unknown UNKNOWN.
Children:
1.1.1.2.1.1.1.1.1. Sir Richard PICKERING
1.1.1.2.1.1.1.1.2. John PICKERING
1.1.1.2.1.1.1.1.3. Joan PICKERING

1.1.1.2.1.1.1.1.4. Robert PICKERING
1.1.1.2.1.1.1.1.5. Hugh PICKERING
1.1.1.2.1.1.1.1.6. Edmund PICKERING
1.1.1.2.1.1.1.1.7. Mathilda PICKERING
1.1.1.2.1.1.1.1.8. Marjory PICKERING

1.1.1.2.1.1.1.2. Roger de PICKERING clerk, master of St. Mary Magdalene Hospital, Ripon, died after 1383.

1.1.1.2.1.1.1.3. Alice de PICKERING prioress of Yedingham Priory, died after 1352.

1.1.1.2.1.1.1.4. John de PICKERING prior of the Austin Friars, York.

9th Generation

1.1.1.2.1.1.1.1.1. Sir Richard PICKERING M.P., Sheriff of Yorkshire, knight, died 11 September 1441, married Margaret UNKNOWN.
Children:
1.1.1.2.1.1.1.1.1.1. Sir John PICKERING
1.1.1.2.1.1.1.1.1.2. Geoffrey de PICKERING
1.1.1.2.1.1.1.1.1.3. Thomas PICKERING

Pickering of Oswaldkirk arms

Pickering of Oswaldkirk 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

1.1.1.2.1.1.1.1.2. John PICKERING controller of Calais, died before 1441, married Cecily UNKNOWN.
Children:
1.1.1.2.1.1.1.1.2.1. Elizabeth PICKERING

1.1.1.2.1.1.1.1.3. Joan PICKERING nun at Nun Monkton.

1.1.1.2.1.1.1.1.4. Robert PICKERING.

1.1.1.2.1.1.1.1.5. Hugh PICKERING.

1.1.1.2.1.1.1.1.6. Edmund PICKERING.

1.1.1.2.1.1.1.1.7. Mathilda PICKERING married John DILCOCK.

1.1.1.2.1.1.1.1.8. Marjory PICKERING married Unknown HORSMAN.

10th Generation

1.1.1.2.1.1.1.1.1.1. Sir John PICKERING knight, Commission of the Peace, controller of great and petty custom Newcastle-upon-Tyne, born c1430, died before 1504, married 1st Joan GREEN (daughter of Sir Thomas GREEN and Marina BELLERS), born Greens Norton, Northamptonshire, died before 1470, married 2nd Margaret EGREMONT (daughter of Thomas PERCY, Lord EGREMONT).
Children of Sir John PICKERING and Joan GREEN:
1.1.1.2.1.1.1.1.1.1.1. Thomas PICKERING
1.1.1.2.1.1.1.1.1.1.2. Elizabeth PICKERING
1.1.1.2.1.1.1.1.1.1.3. Eleanor PICKERING
Children of Sir John PICKERING and Margaret EGREMONT:
1.1.1.2.1.1.1.1.1.1.4. Margaret PICKERING

1.1.1.2.1.1.1.1.1.2. Geoffrey de PICKERING abbot of Byland, North Riding.

1.1.1.2.1.1.1.1.1.3. Thomas PICKERING precentor, later abbot of Whitby abbey, genealogist, died 1475 Whitby, North Riding.

1.1.1.2.1.1.1.1.2.1. Elizabeth PICKERING.

11th Generation

1.1.1.2.1.1.1.1.1.1.1. Thomas PICKERING esquire, died 1509, buried in Christ Church Greyfriars, Newgate, London, married Joan FITZWILLIAM (daughter of Sir Thomas FITZWILLIAM and Margaret HARINGTON), had a child with Jane UNKNOWN servant.
Children of Thomas PICKERING and Joan FITZWILLIAM:
1.1.1.2.1.1.1.1.1.1.1.1. Sir William PICKERING
1.1.1.2.1.1.1.1.1.1.1.2. John PICKERING
1.1.1.2.1.1.1.1.1.1.1.3. Margaret PICKERING
1.1.1.2.1.1.1.1.1.1.1.4. Thomas PICKERING
Children of Thomas PICKERING and Jane UNKNOWN:
1.1.1.2.1.1.1.1.1.1.1.5. Anthony 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

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

1.1.1.2.1.1.1.1.1.1.3. Eleanor PICKERING married William BOROUGH.

1.1.1.2.1.1.1.1.1.1.4. Margaret PICKERING married after 1480 John BARTON (son of Christopher BARTON of Whenby and Margaret DANBY).

12th Generation

1.1.1.2.1.1.1.1.1.1.1.1. Sir William PICKERING knight marshal to Henry VIII, died 1542 Pickering House, St. Mary Street (now St. Mary Axe), Aldgate, London, buried St. Helen’s Bishopsgate, London, married Eleanor FAIRFAX (daughter of Sir William FAIRFAX), had a child with Unknown UNKNOWN.
Children of Sir William PICKERING and Eleanor FAIRFAX:
1.1.1.2.1.1.1.1.1.1.1.1.1. Sir William PICKERING
1.1.1.2.1.1.1.1.1.1.1.1.2. Ann PICKERING
Children of Sir William PICKERING and Unknown UNKNOWN:
1.1.1.2.1.1.1.1.1.1.1.1.3. 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

1.1.1.2.1.1.1.1.1.1.1.2. John PICKERING gentleman, born before 1509, died 1521, married Jane PERCEHAY.
Children:
1.1.1.2.1.1.1.1.1.1.1.2.1. Anthony PICKERING

1.1.1.2.1.1.1.1.1.1.1.3. Margaret PICKERING married Robert TENAUNT.

1.1.1.2.1.1.1.1.1.1.1.4. Thomas PICKERING master of Trinity Hospital, Fossgate, York, married Alice GOLDING.

1.1.1.2.1.1.1.1.1.1.1.5. Anthony PICKERING.

13th Generation

1.1.1.2.1.1.1.1.1.1.1.1.1. Sir William PICKERING knight, M.P., ambassador, born 1517, died 4 January 1575 Pickering House, St. Mary Street (now St. Mary Axe), Aldgate, London, buried St. Helen’s Bishopsgate, London, unmarried, had a child with Unknown UNKNOWN.
Children:
1.1.1.2.1.1.1.1.1.1.1.1.1.1. Hester PICKERING

Sir William's tomb

Sir William Pickering's tomb

Sir William's effigy

Sir William Pickering's effigy
photo: SilverTiger

Sir William's arms (note the chevron or)

Sir William Pickering's arms

St. Helen's then

St. Helen's Bishopsgate then

St. Helen's now

St. Helen's Bishopsgate now

1.1.1.2.1.1.1.1.1.1.1.1.2. Ann PICKERING living 1576, married Roger DELAREUR (DE LA RIVER).

1.1.1.2.1.1.1.1.1.1.1.1.3. George PICKERING.

1.1.1.2.1.1.1.1.1.1.1.2.1. Anthony PICKERING gentleman, born before 1521, buried 8 July 1592 Threekingham, Lincolnshire, married Unknown UNKNOWN.
Children:
1.1.1.2.1.1.1.1.1.1.1.2.1.1. John PICKERING
1.1.1.2.1.1.1.1.1.1.1.2.1.2. Thomas PICKERING
1.1.1.2.1.1.1.1.1.1.1.2.1.3. Isabel PICKERING

14th Generation

Hester Pickering c1580

courtesy of Ashmolean Museum
of Art and Archaeology, Oxford

Hester Pickering c1580 portrait and detail

Hester Pickering c1580
detail of portrait (right)

1.1.1.2.1.1.1.1.1.1.1.1.1.1. Hester PICKERING died 12 May 1592 London, married Boughton Malherbe, Kent, Sir Edward WOTTON (son of Thomas WOTTON and Elizabeth RUDSTON) knight, comptroller of the household to Queen Elizabeth and to James I, ambassador to Portugal born Boughton Malherbe, Kent, died c1625.

1.1.1.2.1.1.1.1.1.1.1.2.1.1. John PICKERING living 1571, married Unknown UNKNOWN.
Children:
1.1.1.2.1.1.1.1.1.1.1.2.1.1.1. John PICKERING

1.1.1.2.1.1.1.1.1.1.1.2.1.1.2. Anthony PICKERING

1.1.1.2.1.1.1.1.1.1.1.2.1.2. Thomas PICKERING yeoman, born before 1574, buried 30 March 1593 Threekingham, Lincolnshire, married Unknown UNKNOWN.
Children:
1.1.1.2.1.1.1.1.1.1.1.2.1.2.1. Anthony PICKERING

1.1.1.2.1.1.1.1.1.1.1.2.1.3. Isabel PICKERING married 20 January 1578 Hedon Ralph WADE bailiff.

The Pickerings of Oswaldkirk are probably the ancestors of the Pickerings of Holderness, but the two trees remain separate until definitive proof of a connection comes to light.

Biographical details available on request.