The above pedigree for John Chesterman is possible though at this stage speculative, derived solely from the earliest Chesterman entries in the Clyffe Pypard burial register.
John Chesterman married Catherine Hedge on 18 Oct 1602 in Clyffe Pypard. Catherine Chesterman was buried there just over a year later. Based on the chronology, Catherine was not the mother of any of John's known children the name of whose mother is unknown.
In 1607 John Chesterman was a witness to the Will of George Farmer als. Hyward of Clyffe Pypard, tailor. John's brother, Michael Chesterman, was one of the overseers of George's Will.
The Will of John Chesterman of Cleeve Peper, Wiltshire, written 30 Aug 1636, proved 28 Nov 1636
[paragraphed for easier reading]
In the name of God Amen The Thirty day of August in the second yeere of the Raigne of king Charles, I John Chesterman of Cleeve Pepper in the County of Wiltes yeoman do Constitute & ordeyne this my last will & Testament in maner & forme followeing.
First I doe bequeath unto Almighty God my Soule to be saved by the meritte & passions of Jesus Christ And my body to be buryed in the Churchyard of Cleeve aforesaid.
Item I geve unto my brother Michaell Chesterman his Children Forty shillings apeece
Item I geve unto John Chesterman my godsonne the sonne of John Chesterman of Bushton forty shillings which money my will is shalbe payde six monthes after my decease
Item I geve unto Francis Chesterman of the parish of Linname my kinsman* Tenn pounds which he oweth unto mee by him And tenn pound more to be payd within three monthes after my decease
Item I geve six shillings eight pence to the Church of Cleeve Peper to be imployed towardes the buying of a Pulpett Cloth.
Item I geve unto the poore of Cleeve Peper six shillings eight pence.
All other my Debts goodes howsehold stuffe, bills bandes I doe bestowe and geve unto my welbeloved wife shee satisfyeing and dischargeing my Legacyes geven aforesaid whome I doe make & ordeyne the sole Executrix of this my last will & Testament
In wittnes whereof I have hereunto sett my hand and Seale the & yeere abovewritten. John Chesterman.
Sealed in the presence of Henry Burford, Henry White
Probate follows in Latin, in which John's wife is identified as Matilda Chesterman, sole executrix.
* John's kinsman Francis Chesterman of Linname can be identified as his nephew, born in 1606 in Lyneham, son of Francis Chesterman of Clack Lyneham (d. 1634) and Alice his wife.