A Y-DNA test taken by an American Pickering whose ancestors came from County Durham reveals matches with men bearing the name Bruce, who were living in eastern Scotland on either side of the Forth of Tay in Fife and Forfarshire in the late 18th century. This can only mean that they shared DNA with the Anglo-Norman de Brus family, which was granted vast estates in both England and Scotland.

The Pickerings emerged in the years following the Norman Conquest, and the Killington family stemmed from the Skelton branch of the de Brus family which held lands in and around the town of Pickering. The names William, Adam, Robert and Richard appear with as much regularity among the families of Pickering and de Brus of Pickering as they do in the two main lines of the de Bruses of Skelton and of Annandale. Furthermore, the de Bruses maintained a clear policy of ensuring that younger sons remained subordinate to the senior line, supporting it as tenants, clerics or administrators, in order to preserve the unity and power of the lordship. Peter III was the last of the Skelton branch of the de Bruses to put this policy into practice. He had acquired estates in Westmorland through his mother, Hawise of Lancaster, and brought William de Pickering over the Pennines to serve as constable and later steward on his estates in Kendal. In c1260 Peter enfeoffed William of his late brother’s manor at Killington, together with Firbank, and Killington manor was to remain in the Pickering family continuously until 1582, when Anne, the last representative of the senior Pickering line, died.

Another factor that points to a relationship between the two families is provided by their arms which show a distinct similarity. The only differences between those of the Yorkshire de Bruses, a lion rampant azure, and those of the Killington Pickerings is that the field is ermine and the lion is crowned or. When the Skelton and Annandale Bruses went their separate ways, the latter adopted as their arms a field or and a chief and saltire gules, though the later arms of the Bruce family of Scotland display both versions: those of Annandale with a Skelton canton. Though a member of the Skelton line, the effigy of Sir William de Brus of Pickering in Pickering church displays the arms of Brus of Annandale, differenced by a saltire engrailed and a chief indented (borne by Robert de Brus V), but it is said that the family used the arms of both branches.

The spelling used for the family’s name is Pickering, although various versions appear in the documents on which this pedigree is based.

1st Generation

1. Thomas de PICKERING married Unknown UNKNOWN.
Children:
1.1. William de PICKERING

2nd Generation

1.1. William de PICKERING born c1220 probably Pickering, North Riding, constable of Kendal c1250, died Killington, Westmorland, married Unknown UNKNOWN, died c1270 Killington, Westmorland.
Children:
1.1.1. Sir Thomas PICKERING

3rd Generation

1.1.1. Sir Thomas PICKERING born c1255 Killington, Westmorland, died c1340, married Elizabeth de GREYSTOKE (daughter of Thomas de GREYSTOKE).
Children:
1.1.1.1. John de PICKERING
1.1.1.2. Richard de PICKERING
1.1.1.3. Robert de PICKERING

4th Generation

1.1.1.1. John de PICKERING died c1335, married Margaret UNKNOWN.

1.1.1.2. Richard de PICKERING parson 1331 Hormead, Hertfordshire; parson 1334 Burton-in-Kendal, Westmorland; parson 1348 Woodford by Thrapston, Northamptonshire.

1.1.1.3. Robert de PICKERING born c1280 Killington, Westmorland, died before 1346, married c1330 Maud UNKNOWN (widow of John de YORK, widow of Walter de OSGODBY).
Children:
1.1.1.3.1. Sir James PICKERING
1.1.1.3.2. John de PICKERING

5th Generation

1.1.1.3.1. Sir James PICKERING knight, Member of Parliament, Speaker of the House of Commons, Sheriff of York, born c1332 Ellerton, East Riding, died c1398, married Agnes UNKNOWN.
Children:
1.1.1.3.1.1. Thomas de PICKERING
1.1.1.3.1.2. Joan de PICKERING
1.1.1.3.1.3. William de PICKERING

1.1.1.3.2. John de PICKERING coroner, burgess of Carlisle.

6th Generation

1.1.1.3.1.1. Thomas de PICKERING escheator 1406 of York, buried 1406 Ellerton Priory, East Riding, married Katharine UNKNOWN buried before 1406 Ellerton Priory, East Riding.
Children:
1.1.1.3.1.1.1. Sir John PICKERING
1.1.1.3.1.1.2. Margaret PICKERING

1.1.1.3.1.2. Joan de PICKERING married Christopher MORESBY born c1360.

1.1.1.3.1.3. William de PICKERING clergyman, granted lands 1382 Thorganby, East Riding.

7th Generation

1.1.1.3.1.1.1. Sir John PICKERING knight, born c1385 Killington, Westmorland, died 23 March 1420, married Helen HARINGTON (daughter of Sir Richard HARINGTON).
Children:
1.1.1.3.1.1.1.1. Sir James I PICKERING
1.1.1.3.1.1.1.2. Margaret PICKERING
1.1.1.3.1.1.1.3. Catherine PICKERING
1.1.1.3.1.1.1.4. Helen PICKERING
1.1.1.3.1.1.1.5. Maria PICKERING
1.1.1.3.1.1.1.6. Alice PICKERING

1.1.1.3.1.1.2. Margaret PICKERING married 1403 Hugh de LAMPLUGH.

8th Generation

1.1.1.3.1.1.1.1. Sir James PICKERING knight, born 29 August 1413 Killington, Westmorland, died before 1474, married 1st Mary LOWTHER (daughter of Sir Robert LOWTHER) died 1430, married 2nd Margaret NORWOOD (daughter of Sir John NORWOOD).
Children of Sir James I PICKERING and Mary LOWTHER:
1.1.1.3.1.1.1.1.1. James II PICKERING
1.1.1.3.1.1.1.1.2. Margaret PICKERING
1.1.1.3.1.1.1.1.3. Isabel PICKERING
1.1.1.3.1.1.1.1.4. Mabel PICKERING
1.1.1.3.1.1.1.1.5. Joan PICKERING
Children of Sir James I PICKERING and Margaret NORWOOD:
1.1.1.3.1.1.1.1.6. Sir Edward PICKERING

1.1.1.3.1.1.1.2. Margaret PICKERING married Sir Robert ROOS.

1.1.1.3.1.1.1.3. Catherine PICKERING married Sir Unknown STAPLETON.

1.1.1.3.1.1.1.4. Helen PICKERING married Thomas BOROUGH.

1.1.1.3.1.1.1.5. Maria PICKERING nun.

1.1.1.3.1.1.1.6. Alice PICKERING born Ellerton, East Riding, married Thomas PALMES esquire, died September 1433 Naburn, East Riding, buried St. George’s, Fishergate, York.

9th Generation

1.1.1.3.1.1.1.1.1. James PICKERING esquire, born Harrington, Cumberland, killed 1460 Battle of Wakefield, Sandal Magna, West Riding, married Margaret UNKNOWN (daughter or widow of Robert or Roger LASCELLES of Escrick) died 17 November 1499.
Children:
1.1.1.3.1.1.1.1.3.1. James PICKERING
1.1.1.3.1.1.1.1.3.2. Margaret PICKERING
1.1.1.3.1.1.1.1.3.3. John PICKERING
1.1.1.3.1.1.1.1.3.4. William PICKERING
1.1.1.3.1.1.1.1.3.5. Christopher PICKERING
1.1.1.3.1.1.1.1.3.6. Ellen PICKERING
1.1.1.3.1.1.1.1.3.7. Unknown PICKERING

The family has ever since quartered the arms of Lascelles with their paternal arms.

1.1.1.3.1.1.1.1.2. Margaret PICKERING married Richard BOTILLER

1.1.1.3.1.1.1.1.3. Isabel PICKERING married John LEYBURN.

1.1.1.3.1.1.1.1.4. Mabel PICKERING married Thomas ACCLAMBY.

1.1.1.3.1.1.1.1.5. Joan PICKERING married Nicholas ACCLAMBY.

1.1.1.3.1.1.1.1.6. Sir Edward PICKERING knighted 1487 Battle of Stoke Field, East Stoke, Nottinghamshire, appointed 1495 constable Holt castle, steward of manors Bromfield cum Yale and Chirk, Denbighshire, Wales, married Joan MASSY (daughter of Sir Geoffrey MASSY, widow of William STANLEY).
Children:
1.1.1.3.1.1.1.1.6.1. Edward PICKERING
1.1.1.3.1.1.1.1.6.2. John PICKERING
1.1.1.3.1.1.1.1.6.3. William PICKERING

10th Generation

1.1.1.3.1.1.1.1.3.1. James PICKERING esquire, born before 1443, died 2 May 1498, married Anne MORESBY (daughter and heir of Sir Christopher MORESBY) died 1523.
Children:
1.1.1.3.1.1.1.1.3.1.1. Anne PICKERING
1.1.1.3.1.1.1.1.3.1.2. Sir Christopher PICKERING
1.1.1.3.1.1.1.1.3.1.3. James PICKERING
1.1.1.3.1.1.1.1.3.1.4. Thomas PICKERING
1.1.1.3.1.1.1.1.3.1.5. William PICKERING

1.1.1.3.1.1.1.1.3.2. Margaret PICKERING born c1444, died after 1469, buried Wighill, West Riding, married c1458 Sir William STAPLETON born c1432, died December 1503, buried Wighill, West Riding.

1.1.1.3.1.1.1.1.3.3. John PICKERING gentleman, born c1456, married Gretton, Northamptonshire Agnes UNKNOWN.
Children of John PICKERING and Agnes UNKNOWN:
1.1.1.3.1.1.1.1.3.3.1. John PICKERING

see Pickerings of Northamptonshire

1.1.1.3.1.1.1.1.3.4. William PICKERING gentleman, Kendal, Westmorland.

1.1.1.3.1.1.1.1.3.5. Christopher PICKERING esquire, appointed 15 September 1500 steward of manors Penrith and Gamblesby, Cumberland.

1.1.1.3.1.1.1.1.3.6. Ellen PICKERING engaged 2 October 1480 to Richard MIDDLETON manservant of the Duke of Gloucester.

1.1.1.3.1.1.1.1.3.7. Unknown PICKERING.

1.1.1.3.1.1.1.1.6.1. Edward PICKERING living 1501 Bromfield, Denbighshire, Wales, died without issue.

1.1.1.3.1.1.1.1.6.2. John PICKERING porter 1502-1510 Holt Castle, Denbighshire, Wales, landholder 1562 Holt, Denbighshire, Wales, married Unknown UNKNOWN.
Children:
1.1.1.3.1.1.1.1.6.2.1. Sir John PICKERING
1.1.1.3.1.1.1.1.6.2.2. Lancelot PICKERING

The relationship between John Pickering and Lancelot Pickering is based circumstantial evidence.

1.1.1.3.1.1.1.1.6.3. William PICKERING

11th Generation

1.1.1.3.1.1.1.1.3.1.1. Anne PICKERING born c1483, married 1st 1515 Sir Robert BELLINGHAM married 2nd 19 October 1541 Sir Richard ASSHETON.

1.1.1.3.1.1.1.1.3.1.2. Sir Christopher PICKERING knight, Sheriff of Cumberland, landholder in Cumberland, Westmorland and Yorkshire, born 1485, knighted 1513 Battle of Flodden Field, died 7 September 1516 Penrith, Cumberland, married Jane or Elizabeth LEWKNER (daughter of Sir Roger LEWKNER).
Children:
1.1.1.3.1.1.1.1.3.1.2.1. Anne PICKERING

1.1.1.3.1.1.1.1.3.1.3. James PICKERING married Elizabeth THRELKELD (daughter of Sir Lancelot THRELKELD and Margaret BROMFLET) inherited 1510 Crosby Ravensworth, Westmorland.
Children:
1.1.1.3.1.1.1.1.3.1.3.1. William PICKERING
1.1.1.3.1.1.1.1.3.1.3.2. Lancelot PICKERING

1.1.1.3.1.1.1.1.3.1.4. Thomas PICKERING holder Yewbarrow Hall, Westmorland, married Unknown UNKNOWN.
Children:
1.1.1.3.1.1.1.1.3.1.4.1. William PICKERING
1.1.1.3.1.1.1.1.3.1.4.2. Thomas PICKERING
1.1.1.3.1.1.1.1.3.1.4.3. Robert PICKERING

1.1.1.3.1.1.1.1.3.1.5. William PICKERING gentleman, died c1588 Cumberland, married Winifred THRELKELD (daughter of Sir Lancelot THRELKELD and Margaret BROMFLET) inherited 1510 Threlkeld, Cumberland.
Children:
1.1.1.3.1.1.1.1.3.1.5.1. Sir Christopher PICKERING
1.1.1.3.1.1.1.1.3.1.5.2. John PICKERING
1.1.1.3.1.1.1.1.3.1.5.3. Thomas PICKERING
1.1.1.3.1.1.1.1.3.1.5.4. Edward PICKERING
1.1.1.3.1.1.1.1.3.1.5.5. Elizabeth PICKERING
1.1.1.3.1.1.1.1.3.1.5.6. Winifred PICKERING
1.1.1.3.1.1.1.1.3.1.5.7. Alice PICKERING
1.1.1.3.1.1.1.1.3.1.5.8. Jane PICKERING
1.1.1.3.1.1.1.1.3.1.5.9. Anne PICKERING

1.1.1.3.1.1.1.1.6.2.1. Sir John PICKERING landholder Hem, Denbighshire, Wales, married Unknown UNKNOWN.
Children:
1.1.1.3.1.1.1.1.6.2.1.1. Francis PICKERING
1.1.1.3.1.1.1.1.6.2.1.2. Elizabeth PICKERING

The relationship between Sir John Pickering and Francis Pickering is based circumstantial evidence.

1.1.1.3.1.1.1.1.6.2.2. Lancelot PICKERING.

see the Pickerings of Kirklington

12th Generation

1.1.1.3.1.1.1.1.3.1.2.1. Anne PICKERING inherited Killington and Firbank, born c1546, died 25 April 1582, married 1st May 1530 Sir Francis WESTON (son of Sir Richard WESTON) knight, born c1511, executed 17 May 1536 for alleged adultery with Queen Anne Boleyn, married 2nd Sir Henry KNEVETT (son of Thomas KNEVETT and Muriel HOWARD) knight, M.P., born East Horseley, Surrey, died before 1564, married 3rd John VAUGHAN High Sheriff of Yorkshire 1594-1595, died before 1582.

In 1547 Anne purchased half of the manor of Sedbergh, West Riding, from Robert Pykeryng, probably the son of the founder of the Puckerings of Flamborough. In 1572 she settled Escrick, East Riding, on her son Henry Knevett, and it passed through his daughter’s husband into the Howard family. With John Vaughan, her third husband, Anne sold her holdings in Cumberland, and their son Francis subsequently sold Killington and Firbank to the manors’ tenants. Finally in 1599 Lord Thomas Knevett, the brother of Henry, sold the two manors of Ellerton, East Riding. These transactions brought to an end the tenure in the East Riding, Cumberland and Westmorland of the Pickerings of Killington.

1.1.1.3.1.1.1.1.3.1.3.1. William PICKERING lawyer, part holder Crosby Ravensworth, Westmorland.

1.1.1.3.1.1.1.1.3.1.3.2. Lancelot PICKERING esquire, J.P., part holder Crosby Ravensworth, Westmorland, married Elizabeth BLENKINSOP (daughter of Thomas BLENKINSOP and Magdalen MUSGRAVE).
Children:
1.1.1.3.1.1.1.1.3.1.3.2.1. Thomas PICKERING

1.1.1.3.1.1.1.1.3.1.4.1. William PICKERING heir, livery 1515 lands Westmorland.

1.1.1.3.1.1.1.1.3.1.4.2. Thomas PICKERING gentleman, co-holder Cark Hall, Lancashire, died 3 November 1584 Stepney, Middlesex, married Margaret STARKEY (daughter of Nicholas STARKEY).
Children:
1.1.1.3.1.1.1.1.3.1.4.2.1. Thomas PICKERING

1.1.1.3.1.1.1.1.3.1.4.3. Robert PICKERING gentleman, holder Isham, Northamptonshire, married Margaret LOWICK (daughter and heir of John LOWICK, gentleman, Isham, Northamptonshire).
Children:
1.1.1.3.1.1.1.1.3.1.4.3.1. Elizabeth PICKERING
1.1.1.3.1.1.1.1.3.1.4.3.2. Thomas PICKERING
1.1.1.3.1.1.1.1.3.1.4.3.3. Ann PICKERING

see Pickerings of Northamptonshire

1.1.1.3.1.1.1.1.3.1.5.1. Sir Christopher PICKERING knight, J.P., M.P., Sheriff of Cumberland, holder Threlkeld, Cumberland, and Ormside, Westmorland, born c1545, unmarried, had a child with Unknown UNKNOWN, died 15 January 1621, buried Ormside, Westmorland.
Children:
1.1.1.3.1.1.1.1.3.1.5.1.1. Frances PICKERING

1.1.1.3.1.1.1.1.3.1.5.2. John PICKERING benefactor Yedingham Priory, joint lord Ellerton, East Riding, married Agnes UNKNOWN.

1.1.1.3.1.1.1.1.3.1.5.3. Thomas PICKERING living 1581 Escrick, married Margaret UNKNOWN.

1.1.1.3.1.1.1.1.3.1.5.4. Edward PICKERING.

1.1.1.3.1.1.1.1.3.1.5.5. Elizabeth PICKERING.

1.1.1.3.1.1.1.1.3.1.5.6. Winifred PICKERING.

1.1.1.3.1.1.1.1.3.1.5.7. Alice PICKERING.

1.1.1.3.1.1.1.1.3.1.5.8. Jane PICKERING.

1.1.1.3.1.1.1.1.3.1.5.9. Anne PICKERING.

1.1.1.3.1.1.1.1.6.2.1.1. Francis PICKERING gentleman, 1632 Mayor of Holt, died 3 September 1635 Holt, Denbighshire, Wales, married Holt, Denbighshire, Wales Margaret WORRALL.
Children:
1.1.1.3.1.1.1.1.6.2.1.1.1. Francis PICKERING

1.1.1.3.1.1.1.1.6.2.1.2. Elizabeth PICKERING married John ALFORD (son of John ALFORD) house owner Beverley, East Riding, landholder Hull area, East Riding, M.P. 1589 Hedon, East Riding, died c1601 Fawley, Buckinghamshire.

13th Generation

1.1.1.3.1.1.1.1.3.1.3.2.1. Thomas PICKERING sold c1615 manor and part demesne Crosby Ravensworth, Westmorland, born Crosby Ravensworth, Westmorland, married Unknown UNKNOWN.
Children:
1.1.1.3.1.1.1.1.3.1.3.2.1.1. Thomas PICKERING

1.1.1.3.1.1.1.1.3.1.4.2.1. Thomas PICKERING yeoman, holder 1582 Cark Hall, settled 1614 property Cark on daughter Anne and her husband Robert Curwen, died Nether Cark, Lancashire, buried 27 January 1617 Cartmel, Lancashire, married Cartmel, Lancashire Agnes UNKNOWN, died Nether Cark, Lancashire, buried 24 August 1616 Cartmel, Lancashire.
Children:
1.1.1.3.1.1.1.1.3.1.4.2.1.1. Isabel PICKERING
1.1.1.3.1.1.1.1.3.1.4.2.1.2. Janet PICKERING
1.1.1.3.1.1.1.1.3.1.4.2.1.3. Ellen PICKERING
1.1.1.3.1.1.1.1.3.1.4.2.1.4. Anne PICKERING

1.1.1.3.1.1.1.1.3.1.5.1.1. Frances PICKERING inherited 1621 property Ormeshead, Threlkeld and Wensdale (sic), married 1st Cyprian HILTON died 1649, married 2nd 26 October 1620 Ormside, Westmorland John DUDLEY (son of Edmund DUDLEY) lawyer, buried 7 March 1623 Ormside, Westmorland.

1.1.1.3.1.1.1.1.6.2.1.1.1. Francis PICKERING soldier, born c1625, leased land Holt, died after 1656 Holt, Denbighshire, Wales.

14th Generation

1.1.1.3.1.1.1.1.3.1.3.2.1.1. Thomas PICKERING married Frances CARUS.
Children:
1.1.1.3.1.1.1.1.3.1.3.2.1.1.1. Lancelot PICKERING

1.1.1.3.1.1.1.1.3.1.4.2.1.1. Isabel PICKERING born Nether Cark, Lancashire, baptised 25 April 1575 Cartmel, Lancashire.

1.1.1.3.1.1.1.1.3.1.4.2.1.2. Janet PICKERING born Nether Cark, Lancashire, baptised 3 February 1579 Cartmel, Lancashire.

1.1.1.3.1.1.1.1.3.1.4.2.1.3. Ellen PICKERING born Nether Cark, Lancashire, baptised 22 March 1581 Cartmel, Lancashire.

1.1.1.3.1.1.1.1.3.1.4.2.1.4. Anne PICKERING heiress Cark Hall, born Nether Cark, Lancashire, baptised 13 April 1583 Cartmel, Lancashire, buried 5 August 1657 Cartmel church, Lancashire, married 20 January 1602 Cartmel, Lancashire Robert CURWEN (son of Walter and Elizabeth CURWEN) cup bearer to Queen Elizabeth, baptised 19 June 1575 Cartmel, Lancashire, buried 2 March 1649 Cartmel, Lancashire.

15th Generation

1.1.1.3.1.1.1.1.3.1.3.2.1.1.1. Lancelot PICKERING baptised 24 September 1620 Crosby Ravensworth, Westmorland.

Sources:
British History Online, Barony of Kendale: https://www.british-history.ac.uk/kendale-barony/vol2
Visitations of the North, Part III, A Visitation of the North of England, circa 1480-1500: https://archive.org/details/visitationsnorth03/page/130
Heraldic Visitation of the Northern Counties in 1530: http://books.google.fr/books?id=ve0OvvM9qr8C
The Visitation of Yorkshire in the years 1563 and 1564: https://archive.org/details/visitationofyork00flow
Visitations of Yorkshire and Northumberland in A.D. 1575
Visitations of the Counties of Cumberland and Westmorland 1615 and 1656: https://archive.org/stream/pedigreesrecorde00sainrich#page/n3
The Visitation of the County of York begun in 1665 and finished in 1666: http://quod.lib.umich.edu/m/moa/ahe1867.0001.001/5?view=image&size=75
Gascoigne Questions, John Watson: https://groups.google.com/g/soc.genealogy.medieval/c/fNvHmqfTaGs/m/Pkm_T3thwhoJ
Pickering of Killington, John Watson: https://groups.google.com/forum/#!msg/soc.genealogy.medieval/NqANTZXJ7vk/y4BW8R2pw7UJ
Killington and Firbank: http://www.british-history.ac.uk/kendale-barony/vol2/pp416-439
Pickerings of Killington / Lascelles of Escrick, Brad Verity: https://groups.google.com/g/soc.genealogy.medieval/c/Ql2T2Zz19M4/m/433emGd9HcYJ
Sir James Pickering of Killington, Westmorland and Selby, Yorkshire: http://www.historyofparliamentonline.org/volume/1386-1421/member/pickering-sir-james-1398
Ellerton.info, A One-Place Study: http://www.bubwith.net/ellerton/index.html
The Pickerings of Barlby, York and Wetherby, P. Spencer Umfreville Pickering: https://dcms.lds.org/delivery/DeliveryManagerServlet?dps_pid=IE2130611
The English Baronetage, volume IV, Thomas Wotton: https://books.google.fr/books?id=KmUUAAAAYAAJ&pg
A genealogical and heraldic history of the extinct and dormant baronetcies of England, John and John Bernard Burke: https://archive.org/details/agenealogicalan03burkgoog
The Brus Family in England and Scotland 1100-c1290, Dr. Ruth Margaret Blakely: http://etheses.dur.ac.uk/1594