Matthew Whipple was born about 1557, most likely in Essex County, England and possibly in the town of Bocking. He married about 1582 to Joan (MNU). She was buried in Bocking on 19 May 1612,

Matthew Whipple the elder of Bocking, Essex, clothier, left a will dated 19 December 1616 and proved 28 January 1618.

New England Historical & Genealogical Register 44:389

My capital messuage or tenement, with the yards, gardens, orchards, members and appurtenances, situated in Bradford Street in Bocking, now in the occupation of me the said Mathewe, from and after my decease shall remain to Mathewe Whippell mine eldest son, upon condition that he shall pay or cause to be paid to my son John Whippell fourscore pounds within three months next after my decease, and to my daughter Jane thirty ponds within six months, and to my daughter Elizabeth thirty pounds within twelve months, and to my daughter Mary thirty pounds at one and twenty or day of her marriage, and to my daughter Amie thirty pounds at one and twenty or day of marriage, upon reasonable demand made by the said Jane, Elizabeth, Mary and Amye. To my daughter Amce (?) six silver spoons of the better sort, two high latten candlesticks, my biggest brass pot and three pounds six shillings and eight pence. To my daughter Johane forty shillings. To my daughter Jane two silver spoons, two pewter platters of the greater sort, one pewter candlestick, one half headed bedstedle, my best flock bed, a flock bolster, a coverlet and a pair of blankets. To my daughter Elizabeth two silver spoons, one pewter candlestick, two pewter platters of the greater sort, a half headed bedstedle , next the best, a floc bed, a floc bolster, a coverlet, a pair of blanks and the little chest which was her mothers. To my daughter Mary two silver spoons, two pewter platters and a pewter salt, a trundle bedsteadle, a flock bed, a flock bolster, a coverlet, a pair of blankets. To my daughter Amye two silver spoons, two pewter platters, a pewter salt, a trundle bedsteadle, a flock bed, a flock bolster and a pair of blankets. To my son John a joyned table and frame standing in my old parlor (and other movables). To my sister, wife of Richard Rathbone twenty shillings, To Hercules Stephens ten shillings. To my grandchildren Hercules Arthur, Margaret Arthur, Henry Caldham and Anne Caldham six shilling eight pence apiece. To the poor of Bocking twenty shillings. All the rest to my son Matthew, sole executor.

Matthew seems to have been fairly well to do, as he left cash gifts totally £200 to his children, aside from silver spoons, furniture and other household goods and his home and land on Bradford Street in Bocking. That would be almost £50,000 today or about $65,000.

Children (All events in Bocking, Essex, England unless otherwise noted):

1. Anne, baptized 1 September 1583; married John Pepper, 13 January 1605/06; not mentioned in her father’s 1616 will
2. Margaret, baptized 28 March 1585; buried 13 February 1608/09; married Lawrence Arthur, 5 July 1603
3. Joan; married Henry Caldam, 6 May 1613 and possibly (2) Nicholas Ives, 16 May 1636
4. Jane, baptized 3 September 1587; married (1) Edward Feast, 15 April 1619 (2) John Wallys, 17 April 1626
5. Matthew, no baptismal entry found, but he is called eldest son, so perhaps born c1590;  died November 1646, Ipswich, Essex, Massachusetts; married (1) Anne Hawkins, 7 May 1622 (2) Rose Barker/Baker, widow of Lionel Chute of Ipswich, between 7 May 1645 and 13 November 1646.
6. Elizabeth, baptized 14 April 1594; married Isaac Greene, 3 September 1618
7. John, baptized 29 August 1596; died about 30 June 1669, Ipswich, Essex, Massachusetts; married (1) Susanna Clarke, 28 August 1621, St. Andrew by the Wardrobe, London, England (2) Jennet (MNU) Dickenson, widow of Thomas Dickenson
8. Mary, born after 1595, as she was under the age of 21 when her father wrote his will in December 1616; married (1) Richard Baker, 9 May 1625
9. Amy, baptized 20 January 1604/05; married William Horton, 31 October 1626

There is a lot of mixed up information about this family to be found online.

From the Essex County, Massachusetts Early Probate Records, 1635-1681, volume 1:87-91, is the will of Matthew Whipple, written the seventh day of the third month (May?) 1645. Inventory of his estate was taken on the 24th day of the ninth month (November?) 1646.

I have to wonder about Matthew Whipple’s marriage to Rose Chute. He updated his will on the 13th day of the ninth month (November?) 1646 and the inventory of his estate happened just 11 days later. It would seem that he recovered from some type of illness at the time he wrote his will in 1645 and was healthy enough to marry again, but either declined or died from a second ailment in 1646.

My line of descent is through Matthew of Bocking who died in 1618 and then through his son John who married Susannah Clarke.

I’ve done no further research into any of the other children beyond what I have posted here and John’s line, but my advice to descendants of Matthew through any of his other children is to not copy, paste and/or merge online data without doing your own research!

There is an excellent starting point. I would highly recommend reading/purchasing The Genealogist, Volume 20, No. 2, Fall 2006, published for The American Society of Genealogists by Picton Press as it contains a well researched article by William Wyman Fiske –  The Whipple Family of Bishops Stortford, Hertfordshire: Proposed Ancestral Origin of Matthew Whipple of Bocking, Essex, and a Whipple Ancestral Line for Arthur Gary of Roxbury, Massachusetts.