The connection between the Pickerings of Oswaldkirk and the Pickerings who lived in the village of Cawton and were buried in the parishes of Gilling East and Hovingham is entirely hypothetical. However, circumstantial evidence points to a link:
• the proximity of Cawton to Oswaldkirk,
• the recurrence of the name George down the generations,
• the name Hester, which is unique to the Oswaldkirk and Cawton Pickerings,
• the relative wealth of the family.

Only a Y-DNA test will establish whether the two families are related. I therefore encourage the male descendants of the later Pickerings of Cawton (who are relatively sure that there is no “non paternal event” in their line) to take the test.

15th Generation

(1.1.3.1.1.3.1.1.1.1.1.1.1.1.)4. George PICKERING born c1540, married c1560 Unknown UNKNOWN.
Children:
(1.1.3.1.1.3.1.1.1.1.1.1.1.1.)4.1. Unknown PICKERING.

16th Generation

(1.1.3.1.1.3.1.1.1.1.1.1.1.1.)4.1. Unknown PICKERING born c1560, married c1580 Unknown UNKNOWN.
Children:
(1.1.3.1.1.3.1.1.1.1.1.1.1.1.)4.1.1. Unknown PICKERING

17th Generation

4.1.1. Unknown PICKERING born c1580, married 1600 Unknown UNKNOWN.
Children:
4.1.1.1. George PICKERING
4.1.1.2. John PICKERING
4.1.1.3. William PICKERING

18th Generation

4.1.1.1. George PICKERING yeoman, Sandwith Grange, Oswaldkirk, North Riding, born c1600, died Cawton, North Riding, buried 1 October 1661 Gilling East, married 1635 Mary TURNER born Dalby, North Riding.
Children:
4.1.1.1.1. Thomas PICKERING
4.1.1.1.2. Ann PICKERING
4.1.1.1.3. Unknown PICKERING

4.1.1.2. John PICKERING born c1610, died Cawton, North Riding, buried 27 April 1697 Gilling East, married 14 August 1632 Hovingham, North Riding Ann PECKITT buried February 1661 Hovingham, North Riding.
Children:
4.1.1.2.1. James PICKERING
4.1.1.2.2. Hester PICKERING
4.1.1.2.3. Elizabeth PICKERING
4.1.1.2.4. Jane PICKERING

4.1.1.3. William PICKERING born c1620, buried 15 November 1681, Hovingham, North Riding, married c1640 Jane PICKERING buried May 1681 Hovingham, North Riding.
Children:
4.1.1.3.1. William PICKERING
4.1.1.3.2. Sarah PICKERING
4.1.1.3.3. Unknown PICKERING
4.1.1.3.4. John PICKERING

19th Generation

4.1.1.1.1. Thomas PICKERING baptised 12 November 1635 Oswaldkirk.

4.1.1.1.2. Ann PICKERING born Scackleton, North Riding, baptised 3 June 1639 Hovingham, North Riding.

4.1.1.1.3. Unknown PICKERING died Scackleton, North Riding, buried April 1642 Hovingham, North Riding.

4.1.1.2.1. James PICKERING born South Holme, North Riding, baptised 14 October 1632 Hovingham, North Riding, married Elizabeth UNKNOWN buried 27 August 1670 Hovingham, North Riding.
Children:
4.1.1.2.1.1. Ann PICKERING
4.1.1.2.1.2. Elizabeth PICKERING

4.1.1.2.2. Hester PICKERING baptised 12 February 1637 Hovingham, North Riding.

4.1.1.2.3. Elizabeth PICKERING baptised 6 October 1639 Hovingham, North Riding.

4.1.1.2.4. Jane PICKERING baptised 22 January 1646 Hovingham, North Riding.

4.1.1.3.1. William PICKERING born Howthorpe, North Riding, baptised 12 May 1644 Hovingham, North Riding, married Unknown UNKNOWN.
Children:
4.1.1.3.1.1. Unknown PICKERING

4.1.1.3.2. Sarah PICKERING born Baxtonhowe, North Riding, baptised 3 March 1647 Hovingham, North Riding.

4.1.1.3.3. Unknown PICKERING born Baxtonhowe, North Riding, baptised 2 February 1651 Hovingham, North Riding.

4.1.1.3.4. John PICKERING buried 20 November 1659 Hovingham, North Riding.

20th Generation

4.1.1.2.1.1. Ann PICKERING baptised 10 August 1664 Hovingham, North Riding.

4.1.1.2.1.2. Elizabeth PICKERING baptised 27 August 1670 Hovingham, North Riding.

4.1.1.3.1.1. Unknown PICKERING born c1670, married Unknown UNKNOWN.
Children:
4.1.1.3.1.1.1. Matthew PICKERING
4.1.1.3.1.1.2. George PICKERING

21st Generation

4.1.1.3.1.1.1. Matthew PICKERING born c1710, buried 13 May 1767 Appleton-le-Street, North Riding, married 20 April 1731 Appleton-le-Street, North Riding Elizabeth HARPER buried 3 July 1782 Appleton-le-Street, North Riding.
Children:
4.1.1.3.1.1.1.1. Richard PICKERING
4.1.1.3.1.1.1.2. George PICKERING
4.1.1.3.1.1.1.3. Mary PICKERING
4.1.1.3.1.1.1.4. Isabel PICKERING
4.1.1.3.1.1.1.5. Matthew PICKERING

4.1.1.3.1.1.2. George PICKERING post office assistant, born c1720, buried 14 August 1785 Appleton-le-Street, North Riding, married 29 March 1741 Appleton-le-Street, North Riding Mary NATTRISS buried 15 December 1797 Appleton-le-Street, North Riding.
Children:
4.1.1.3.1.1.2.1. Stephen PICKERING
4.1.1.3.1.1.2.2. George PICKERING
4.1.1.3.1.1.2.3. Mary PICKERING
4.1.1.3.1.1.2.4. John PICKERING
4.1.1.3.1.1.2.5. Isabel PICKERING
4.1.1.3.1.1.2.6. Jane PICKERING

22nd Generation

4.1.1.3.1.1.1.1. Richard PICKERING baptised 17 July 1732 Appleton-le-Street, North Riding, buried 20 July 1732 Appleton-le-Street, North Riding.

4.1.1.3.1.1.1.2. George PICKERING baptised 10 July 1733 Appleton-le-Street, North Riding, buried 20 April 1804 Malton, North Riding.

4.1.1.3.1.1.1.3. Mary PICKERING baptised 3 August 1735 Appleton-le-Street, North Riding, buried 28 February 1813 Appleton-le-Street, North Riding.

4.1.1.3.1.1.1.4. Isabel PICKERING baptised and buried 15 April 1739 Appleton-le-Street, North Riding.

4.1.1.3.1.1.1.5. Matthew PICKERING baptised 11 July 1742 Appleton-le-Street, North Riding, buried 21 July 1818 Malton, North Riding, married 22 August 1774 Malton, North Riding Catherine ANDERSON (daughter of Christopher ANDERSON) baptised 22 June 1745 Malton, North Riding.
Children:
4.1.1.3.1.1.1.5.1. George PICKERING
4.1.1.3.1.1.1.5.2. Matthew PICKERING
4.1.1.3.1.1.1.5.3. Mary PICKERING
4.1.1.3.1.1.1.5.4. Elizabeth PICKERING
4.1.1.3.1.1.1.5.5. Christopher PICKERING

4.1.1.3.1.1.2.1. Stephen PICKERING baptised 2 February 1742 Appleton-le-Street, North Riding, buried 21 November 1772 Appleton-le-Street, North Riding, married 29 January 1765 Slingsby, North Riding Eleanor HORNER buried 20 April 1779 Appleton-le-Street, North Riding.
Children:
4.1.1.3.1.1.2.1.1. Mary PICKERING
4.1.1.3.1.1.2.1.2. Stephen PICKERING
4.1.1.3.1.1.2.1.3. Helen PICKERING
4.1.1.3.1.1.2.1.4. Ellen PICKERING

4.1.1.3.1.1.2.2. George PICKERING baptised 21 October 1744 Appleton-le-Street, North Riding, buried 28 February 1790 Appleton-le-Street, North Riding, married 5 October 1771 Appleton-le-Street, North Riding Jane SMITH.
Children:
4.1.1.3.1.1.2.2.1. George PICKERING

4.1.1.3.1.1.2.3. Mary PICKERING baptised 6 March 1748 Appleton-le-Street, North Riding, married 7 December 1773 Appleton-le-Street, North Riding George BOSS.

4.1.1.3.1.1.2.4. John PICKERING baptised 27 December 1751 Appleton-le-Street, North Riding, buried 17 April 1803 Appleton-le-Street, North Riding, married 22 December 1779 Appleton-le-Street, North Riding Mary GRAY.
Children:
4.1.1.3.1.1.2.4.1. John PICKERING

4.1.1.3.1.1.2.5. Isabel PICKERING baptised 16 April 1756 Appleton-le-Street, North Riding, buried 2 June 1756 Appleton-le-Street, North Riding.

1.1.1.3.1.1.2.6. Jane PICKERING baptised 9 April 1777 Appleton-le-Street, North Riding, buried 15 August 1800 Appleton-le-Street, North Riding.

23rd Generation

4.1.1.3.1.1.1.5.1. George PICKERING post office assistant, baptised 24 September 1775 Malton, North Riding.

4.1.1.3.1.1.1.5.2. Matthew PICKERING baptised 13 March 1777 Norton, East Riding, living independent means 1841 Leicester, Leicestershire, married Sarah UNKNOWN born c1778, died before 1851.
Children:
4.1.1.3.1.1.1.5.2.1. Charles PICKERING
4.1.1.3.1.1.1.5.2.2. Henry PICKERING
4.1.1.3.1.1.1.5.2.3. Christopher PICKERING

4.1.1.3.1.1.1.5.3. Mary PICKERING baptised 8 May 1779 Norton, East Riding, buried 6 October 1812 Malton, North Riding.

4.1.1.3.1.1.1.5.4. Elizabeth PICKERING baptised 6 May 1781 Norton, East Riding, married 12 April 1803 Malton, North Riding John STAMPER.

4.1.1.3.1.1.1.5.5. Christopher PICKERING gentleman, book keeper, bacon factor, attorney, baptised 4 July 1785 Norton, East Riding, married 1st 20 October 1807 Malton, North Riding Ann JEFFERSON, married 2nd 1844 Leeds, West Riding Elizabeth HOPTON born c1806 Leeds, West Riding.
Children of Christopher PICKERING and Ann JEFFERSON:
4.1.1.3.1.1.1.5.5.1. Henrietta PICKERING
4.1.1.3.1.1.1.5.5.2. George PICKERING
4.1.1.3.1.1.1.5.5.3. Emma PICKERING
4.1.1.3.1.1.1.5.5.3. Christopher PICKERING
Children of Christopher PICKERING and Elizabeth HOPTON:
4.1.1.3.1.1.1.5.5.5. Matthew Henry PICKERING

4.1.1.3.1.1.2.1.1. Mary PICKERING baptised 7 August 1765 Appleton-le-Street, North Riding, buried 8 August 1765 Appleton-le-Street, North Riding.

4.1.1.3.1.1.2.1.2. Stephen PICKERING baptised 4 July 1767 Appleton-le-Street, North Riding.

4.1.1.3.1.1.2.1.3. Helen PICKERING baptised 7 April 1769 Appleton-le-Street, North Riding, buried 19 September 1771 Appleton-le-Street, North Riding.

4.1.1.3.1.1.2.1.4. Ellen PICKERING baptised 20 October 1771 Appleton-le-Street, North Riding, married 29 October 1798 Malton, North Riding William WEBSTER.

4.1.1.3.1.1.2.2.1. George PICKERING baptised 2 March 1772 Appleton-le-Street, North Riding.

4.1.1.3.1.1.2.4.1. John PICKERING baptised 23 May 1780 Appleton-le-Street, North Riding, buried 31 May 1780 Appleton-le-Street, North Riding.

24th Generation

4.1.1.3.1.1.1.5.2.1. Charles PICKERING baptised 2 November 1817 Melton Mowbray, Leicestershire.

4.1.1.3.1.1.1.5.2.2. Henry PICKERING chemist and druggist, 30 April 1820 Melton Mowbray, Leicestershire, died 1872 Leicester, Leicestershire.

4.1.1.3.1.1.1.5.2.3. Christopher PICKERING baptised 14 April 1822 Melton Mowbray, Leicestershire.

4.1.1.3.1.1.1.5.5.1. Henrietta PICKERING baptised 25 March 1811 Malton, North Riding, married 17 January 1835 Malton, North Riding George GREEN.

4.1.1.3.1.1.1.5.5.2. George PICKERING farmer, baptised 9 December 1812 Malton, North Riding, married 13 July 1842 Settrington, North Mary RICHARDSON (daughter of George and Hannah RICHARDSON) born 29 November 1820 Settrington, North Riding.
Children:
4.1.1.3.1.1.1.5.5.2.1. Henry Jefferson PICKERING

4.1.1.3.1.1.1.5.5.3. Emma PICKERING baptised 13 July 1814 Malton, North Riding, married 1 February 1841 Norton, North Riding John AVISON.

4.1.1.3.1.1.1.5.5.3. Christopher PICKERING painter, born 11 July 1816 Malton, North Riding, married 1840 Leeds, West Riding Caroline SAMPTON straw hat maker, born c1821 Sheffield, West Riding.
Children:
4.1.1.3.1.1.1.5.5.3.1. George PICKERING
4.1.1.3.1.1.1.5.5.3.2. Christopher PICKERING

4.1.1.3.1.1.1.5.5.5. Matthew Henry PICKERING born 1849 Wortley, West Riding.

25th Generation

4.1.1.3.1.1.1.5.5.2.1. Henry Jefferson PICKERING shoemaker, railway platelayer, hawker, rent collector, baptised 20 August 1843 Norton, East Riding, married 1869 Halifax, West Riding Ellen BULL born c1845 Newport Pagnell, Buckinghamshire.
Children:
4.1.1.3.1.1.1.5.5.2.1.1. Alfred PICKERING
4.1.1.3.1.1.1.5.5.2.1.2. Mary PICKERING
4.1.1.3.1.1.1.5.5.2.1.3. Emily PICKERING
4.1.1.3.1.1.1.5.5.2.1.5. Arthur PICKERING
4.1.1.3.1.1.1.5.5.2.1.6. Walter PICKERING

4.1.1.3.1.1.1.5.5.3.1. George PICKERING born c1842 Leeds, West Riding

4.1.1.3.1.1.1.5.5.3.2. Christopher PICKERING born c1846 Leeds, West Riding

26th Generation

4.1.1.3.1.1.1.5.5.2.1.1. Alfred PICKERING born c1871 Halifax, West Riding.

4.1.1.3.1.1.1.5.5.2.1.2. Mary PICKERING born c1872 Copley, West Riding.

4.1.1.3.1.1.1.5.5.2.1.3. Emily PICKERING born c1873 Cote Hill, Halifax, West Riding.

4.1.1.3.1.1.1.5.5.2.1.4. Henry PICKERING born 1875 Cote Hill, Halifax, West Riding.

4.1.1.3.1.1.1.5.5.2.1.5. Arthur PICKERING born 1879 Cote Hill, Halifax, West Riding.

4.1.1.3.1.1.1.5.5.2.1.6. Walter PICKERING born 1880 Cote Hill, Halifax, West Riding.