Mr. CALLINGWOOD had children:
1. Peter CALLINGWOOD b. ca. 1570;28 m. Anna;29 d. between 14 Feb. 1644 to 22 Nov. 1645
   Trusley, Derbyshire30
2. John CALLINGWOOD b. about 1580;31 m. Jane GREENE;26 bur. 9 Jan. 1621 [1621/2] Rolleston,
   Staffordshire1
3. Richard CALLINGWOOD26 m. Frances ARBLASTER;32 d. between 22 Mar. 1642 to
   22 July 1645, Caldwell, Derbyshire33

John CALLINGWOOD lived at Anslow, Rolleston Parish, Staffordshire,
England, but his ancestry probably lies a few miles away in Caldwell
or Stapenhill, Derbyshire, England.  

"In 1068 the Manor of Caldwell was given to the Abbey of Burton by
William the Conqueror, and it was held by them until the Dissolution of the
Monasteries. (Richard de Calingewood is recorded as tenant here in 1351)...
In 1545 Henry VIII gave the Manor of Caldwell to Sir William Paget.
His son Henry, Lord Paget, sold it in 1555 to Peter Collingwood, (or he
bought it in 1564?)"34 That Peter died testate in 1586, but how
John or his brothers are related is not known at this time.

Another interesting article about the origin of the name Callingwood also
mentions Richard de Callangwode in 1324.35

John's wife was Jane GREENE.26 They had eight children baptized
at Rolleston, to which Anslow belonged. His will only named his youngest
son William, but stated he had eight children. The probate of the will
named the minors as Sara, John, Jane, Anne, Elizabeth,Thomas, Walter,
and William, matching those in the parish records.26

Important mentions in his will were that if his wife died before his youngest
child reached age 21, then John Greene and Walter Greene, "my brothers in law",
Peter Callingwood "my natural brother", and Richard Callingwood "my brother in law"
were to have tuition of the children.26  It may be that Richard married
a sister of John, or the term was sometimes used to describe a half brother. 

The probate of the will indicated that Walter Greene was at Burton upon Trent.26 
John's inventory was taken before Peter CALLINGWOOD of Trusley, County of Derby, 
Richard CALLINGWOOD of Caldwell in the County of Derby, and others.27 

Wills were examined for the Diocese of Lichfield, which included Staffordshire,
Derbyshire, Shropshire, and Warwickshire. Other than the will for John's brother 
Peter at Trusley, all the wills were at Stapenhill/Caldwell. Those were:
Richard Calyngwood, 1538 Stapenhill 
John Calyngewodd, 1555 Caldwell
Ralph Kalengwood 1558 Stapenhill
William Calyngwod 1561 Stapenhill
John Calyngewood, 1578/9 Stapenhill
Peter Callingwood 1586 Caldwell
William Callingwood 1610 Caldwell
Thomas Callengwood 1616 Caldwell
Thomas Callengwood 1638 Caldwell
William Callengwood 1638 Caldwell
Peter Callingwood 1645 Trusley
Richard Callengwood 1645 Caldwell
Those wills were examined, and no connection to John or his brothers Peter
and Richard was found. Caldwell is a chapelry within Stapenhill. Unfortunately
the parish registers for Stapenhill [Caldwell] don't survive before 1679, and the
Bishop's Transcripts don't survive before 1663. 

Caldwell, Stapenhill, Rolleston, Anslow, and Barton under Needwood are all
within a few miles of each other, as is Burton upon Trent where Walter
Greene lived after his marriage at Rolleston. 

John CALLINGWOOD and Jane GREENE had children:
1. Sara CALLINGWOOD bap. 2 Dec. 1607;1 m. George WRAY 13 Nov. 1634;4
2. John CALLINGWOOD bap. 16 May 1609;1 m.1. -?- -?-;5 m.2 Sarah (widow)5 ALLEN5 9 Sep. 1682;6
   d. between 7 Dec. 1685 and 23 Feb. 1685 [1685/6] London, England3
3. Jane CALLINGWOOD bap. 29 Apr. 1610;1 (m. Mr. BEAVER)?
4. Anne CALLINGWOOD bap. 5 Feb. 1611 [1611/2];1 m. Thomas GASSAWAY 6 Jan. 1631 [1630/1]
   bur. 26 May 1647 St. Margaret's, Westminster, Middlesex, England4
5. Elizabeth CALLINGWOOD bap. 14 Mar. 1613 [1613/4]1 m. (Mr. READING)?
6. Thomas CALLINGWOOD bap. 1 Feb. 1615 [1615/6];1 m. Katherne [Catherine] WESSON
   2 June 1640;9
7. Walter CALLINGWOOD26 bap. 23 Mar. 1617 [1617/8]1
8. William CALLINGWOOD26 b. 1 May 1620;1

That Anne Callingood who married Thomas Gassaway and John CALLINGWOOD
of London are siblings is certain. Anne's son Nicholas GASSAWAY in his
Anne Arundel County, Maryland, will mentioned a bequest left by
his Uncle John CALLINGWOOD of London,2 and John's will named
his "Nephew Nicholas GAHSAWAY."3

There are several indications that the family at Rolleston is the correct
identity of Anne and brother John. On the marriage allegation for John
Collingwood in 1682 as a widower, he was age 73, matching the birth date
of John at Rolleston.5

In his will John CALLINGWOOD was identified as an Armorer. John was
granted his freedom on 20 November 1633 by order of the Lord Mayor and
Court of Alderman.7 While most freedom listings contained the name
of the apprentice's father and prior residence, as well as their master, the
entry for John CALLINGWOOD did not. No listing of when he was apprenticed
was found. Most had typically been bound either 7 or 9 years, and John
had probably been apprenticed after the death of his mother in late 1625.

After obtaining his freedom, John CALLINGWOOD also had several apprentices 
throughout the years. The most important is that two children of Thomas
CALLINGWOOD of Walsall, Staffordshire, were apprenticed to John. Thomas
was apprenticed on 20 December 1661, and John on 10 June 1662.8
Rolleston is about 28 miles, from Walsall. The probable age of Thomas 
CALLINGWOOD based on his 1640 marriage is consistent with the Thomas
born 1615/6 at Rolleston, and no other candidates to be the Thomas who
married in 1640 have been located other than the one born at Rolleston.

A connection is indicated with the BEAVER family. Nicholas 
GASSAWAY [Sr.] in his will had indicated that the bequest left
him by his uncle John CALLINGWOOD in London was in the possession
of his "cousin Samuel BEAVER."2 John CALLINGWOOD in his will mentioned
his niece Elizabeth BEAVER and also left a bequest to Jane BEAVER
who was living with him at the time he wrote his will. It may be
Jane BEAVER living with him is identical to his sister Jane.

John CALLINGWOOD's will also named his "sister READING's" granddaughter
Jane WARD and his "cousin Callingwood WARD." This WARD family is found
at Barton-under-Needwood, Staffordshire, which is about 9 miles from
Rolleston, and 19 miles from Walsall. The location of this WARD family
named in John CALLINGWOOD's will supports that John was the person
born close by at Rolleston, and that his brother Thomas moved to Walsall.
Callingwood WARD also went to Anne Arundel Co., MD, where he married, and
Nicholas Gassaway lived. Collingwood WARD named his first child Godfrey,
after his father, adding further support to the Rolleston connection being
correct. 

It is also noteworthy that the birth of Anne CALLINGWOOD in 1611/2 is
consistent with her 1631 marriage to Thomas GASSAWAY. 

An additional connection is that John CALLINGWOOD in his will made a
bequest to Samuel WRAY, with no relationship stated. There was a
Sara CALLINGWOOD who married George WRAYE at St. Margaret's,
Westminster Church in London, the same church where Anne CALLINGWOOD
married Thomas GASSAWAY.23 That marriage would be for John
and Anne's sister Sara, who did have a son Samuel [W]RAY.

A relation with the LEAFE family is indicated. John CALLINGWOOD
left bequests to Sarah LEAFE and to Sarah LEAFE's sister CALLINGWOOD
dwelling in Staffordshire. The 1698 Calvert Co., MD will of Francis
LEAFE made his "cousin Nicholas GASSAWAY" [Jr.] one of his executors.10 
That Nicholas was the grandson of Thomas GASSAWAY and Anne CALLINGWOOD,
as his father Nicholas had died in 1691/2. 

Francis LEAFE had two wives. The wife named in his will at the time
of his death was named Anne. Francis LEAFFE of Anne Arundel County
by 1679 had transorted himself, Sarah, his wife, Francis, his son,
Jane Eaton, his daughter, & John Hoane, his servant.22

Francis LEAFE's will also stated that "I desire my Cozen Gassaway
to see that money and Estate in England be recovered for my Children." 
That statement implies that:
1. There was an inheritance from England that was through his
   deceased wife Sarah, as it was for his children.
2. Since Nicholas GASSAWAY, Jr., was appointed to recover it, that
   it was due from John CALLINGWOOD's will.
Those would suggest that the Sarah LEAFE named in John CALLINGWOOD's
will was identical to Francis LEAFE's wife Sarah. As Sarah had a 
sister CALLINGWOOD in Staffordshire, it would seem likely she was
Sarah, born in 1641, the daughter of Thomas CALLINGWOOD.

The given name of the "Sister Reading" named in the will of John
CALLINGWOOD is not known. From elimination of the spouses of the
other daughters, that sister may have been Elizabeth. 
(Elizabeth)? CALLINGWOOD b. 1613/4; m. Mr. READING;3
    1. daughter READING b. say 1631; m. -?- -?-
        1. Jane -?-;1 b. say 1648 m. Godfrey WARD; they had 
           children baptized at Barton Under Needwood, Staffordshire
            1. Francis WARD b. 13 Jan. 1664;11 bur. 25 Jan. 1664;12
	    2. Callingwood WARD b. 31 Dec. 1665;13 m. March 1694 Alice LASKE,
               All Hallow's Parish, Anne Arundel Co., MD23; living 1711;25
	        1. Godfrey WARD b. 10 Mar. 1695;24
            3. Jane WARD b. 10 Sep. 1667;14
            4. Philip WARD b. 18 Mar. 1669;15 bur. 31 Mar. 1669;16
            5. Dorathy WARD bap. 12 May 1671;17

Sara CALLINGWOOD and husband George WRAY had known children:
   1. Mary WRAY bap. 20 May 1640;18
   2. John WRAY bap. 19 June 1642;19
   3. Samuel WRAY1 bap. 28 Jan. 1646;20

(Jane)? CALLINGWOOD who m. Mr. BEAVER had known children:
   1. Samuel BEAVER2
   2. Elizabeth BEAVER3

Thomas COLLINGWOOD and wife Katherine/Catherine WESSON had known children,
who were all baptized at Wallsal, Stafforshire:
   1. Sarah CALLINGWOOD bap. 6 July 1641;9 m. Francis LEAFE;
      d. 1679 to 1698 MD
   2. Thomas CALLINGWOOD b. 16 Aug. 1643;9
   3. [Jane]? bap. 26 March 1645;9
   4. John CALLINGWOOD  bap. 18 Aug. 1647;21
   5. Mary CALLINGWOOD bap. 13 Jan. 1649 [1649/50];21
   6. Anne CALLINGWOOD bap. 28 Nov. 1652;21


1. Rolleston, Staffordshire, 1569-1724 General Register, FHL Microfilm 1526108.
2. Nicholas Gassaway Senr. will, MD wills 2:228-231 [image 229 of 412].
3. John Callingwood will, Peculiars of the Deaneries of the Arches (London),
   Shoreham & Croydon, Wills S. & C. 1679-1684, L. S. & C.  1684/5-1689, Volume 2,
   page 201 verso, FHL Microfilm 91792, Item 1.
   John Callingwood will transcription.
4. Arthur Meredyth Burke, Memorials of St. Margaret;s Church, Westminster:
   Comprising the Parish Registers, 1539-1660, and the Churchwardens' Accounts,
   1460-1603, (London: Eyre & Spottiswoode, 1914).
5. George J. Armytage, _Allegations for Marriage Licenses Issued by the Vicar-General
   of the Archbishop of Canterbury, July 1679 to June 1687_, (London: Harleian Society, 1890),
   p. 106 [image 110/355]. 
6. "England Marriages, 1538–1973," database, FamilySearch, John Callingwood and Sarah Allen
   citing Saint Gabriel Fenchurch, London, London, England, reference, index based on FHL Microfilm
   394830.
7. Armourer's and Brasiers Company, Apprentice Bindings and Freedom Admissions, 
   Volume 12079 / 2, 1603-1661, p. 77, FHL Microfilm 1469188, Item 3.
8. Rootchat listing. 
9. Frederic W. Willmore, Transcript of the First Register Book of the Parish Church
   of Saint Matthew, Walsall, 1570-1649, (Walsall, England: W. H. Robinson, 1890).
     p. 295 Thomas Callingswood et Katherne Wesson 
     p. 130 Sara Callingswood fil Thomas
     p. 134 Thomas Kallingswood fil Thomas
     p. 139 Jane Rallingswood (sic) fil Thomas
10. Francis Leafe will, Maryland Wills 6:194-196 [imdage 198 of 493].
11. "England, Staffordshire, Church Records, 1538-1944", database, FamilySearch, Francis Ward, 13 Jan. 1664.
12. "England, Staffordshire, Church Records, 1538-1944", database, FamilySearch, Francis Ward, bur. 25 Jan. 1664.
13. "England, Staffordshire, Church Records, 1538-1944", database, FamilySearch, Callingwood Ward, 23 Jan. 1665.
14. "England, Staffordshire, Church Records, 1538-1944", database, FamilySearch, Jane Ward, 10 Sep. 1667.
15. "England, Staffordshire, Church Records, 1538-1944", database, FamilySearch, Phillip Ward, 18 Mar. 1669.
16. "England, Staffordshire, Church Records, 1538-1944", database, FamilySearch, Phillip Ward, 31 Mar. 1669.
17. "England, Staffordshire, Church Records, 1538-1944", database, FamilySearch, Darathy Ward, 12 May 1671.
18. "England Births and Christenings, 1538-1975," database, FamilySearch, Mary Wray, 20 May 1640.
19. "England Births and Christenings, 1538-1975," database, FamilySearch, John Wray, 19 June 1642.
20. "England Births and Christenings, 1538-1975," database, FamilySearch, Samuel Wray, 28 Jan. 1646.
21. Norman W. Tildesley, Wallsal Parish Registers, Marriages 1663-1754, Baptisms 1646-1678 (Wednesfeld, England:
    Staffordshire Parish Registers Society), FHL Book 942.46 B4pr v. 70.
      p. 86 John s. of Thomas and Cathren Challingwood  
      p. 89 Mary d. of Thomas and Catherine Callingwood
      p. 94 Anne d. of Thomas and Catherine Callingwood
22. Maryland Patents WC2, p.60 [image 34 of 233.
23. All Hallow's Parish Register, Anne Arundel Co., MD, p. 4 [image 18/227]
24. All Hallow's Parish Register, Anne Arundel Co., MD, p. 17 [image 9/227]
25. Beaufort Co., NC, Record of Deeds 1:156. 
26. John Callingwood will, Diocese of Lichfield, Episcopal Consistory Court,
    Original wills, administrations, inventories, C 1621-1625, FHL DGS 7620763.
    John Callingwood inventory and will transcription.
27. John Callingwood inventory, Diocese of Lichfield, Episcopal Consistory Court,
    Original wills, administrations, inventories, C 1621-1625, FHL DGS 7620763.
28. Estimate from first child baptized at Trusley in 1597.
29. Trusley, Devonshire, Parish Register.
30. Peter Callingwood will, Prerogative Court of Canterbury wills, 1644-1645,
    140 Rivers, FHL DGS 8310478.
31. Estimate from first child baptized in 1607.
32. John Sleigh, A History of the Ancient Parish of Leek in Staffordshire:
    Including Horton, Cheddleton, and Ipstones, (London, Bemrose & Sons, 1883), 
    p. 163.
33. Richard Callingwood will, Diocese of Lichfield, Episcopal Consistory Court,
    Original wills, administrations, inventories, C 1645, FHL DGS 7621421.
34. The History of Caldwell.
35. Robin Sydney Collingwood, "On the possible origins of the name
    Collingwood in the north of England, (R S Collingwood, 2014).