To accurately follow the Woodruffs, it is necessary to also follow John Woodruff’s stepfather, John Gosmer, and his mother, Elizabeth Cartwright, who married Gosmer just 15 days after the death of John’s father.

Young John Woodruff, born c1604, who had been living in St. Mary Northgate with his parents, returned to Fordwich with his mother’s remarriage.

As a young man, he ventured to nearby Nonington, where he married Ann Ward on 8 October 1627. Little is known about this couple, given the time period and the fact that in the late 1630s, the Gosmers and Woodruffs left England for Massachusetts.

Whether they traveled as one family group is uncertain, but it is likely they did. John Woodruff’s son, John, was reportedly baptized in Sturry, Kent, England on 16 April 1637, not long before the trip across the ocean would have been made. Although I have found the transcription of this baptism, there are MANY John Woodruffs living in this area of Kent in the early-to-mid-1600s. I have no idea how early family historians sorted out these people.

To better understand this family, there are some details shared in Francis Woodruff’s 1908 book, The Woodruffs of New Jersey who came from Fordich, Kent, England by way of Lynn, Massachusetts, and Southampton, Long Island.

First, regarding John Gosmer – he may have been the “push” factor that influenced the extended family’s decision to leave England when they did.

For the back story – Gosmer is not a particularly common surname in England. In addition to John Gosmer marrying the widowed Elizabeth Woodruff in 1611, there is a second marriage record in 1618 for one John Gosmer, bachelor, marrying widow Ann Woodruff at St. Mary Northgate.

Nothing is known of John Gosmer Sr.’s life before he married Elizabeth in 1611, including his birth year. He may have been old enough to have had a previous marriage with a son born, say 1595, who would have been of marriageable age in 1618. What became of the younger John Gosmer is unknown.

Next, in 1613, John Gosmer, an assistant to the church warden, signed a record of the christenings, marriages and burials in St. Mary Northgate.

Further, John Gosmer was involved in a business dispute with the Fordwich Corporation in his role as a tenant of the Chapter of
Canterbury. I’m not sure exactly what these entities were but this was apparently died to the town resisting the payment of ship-money (shipping tax, perhaps) demanded by King Charles on the cusp of the English Civil War. In 1639, the government repeated its demand for this money to be paid by “Mr. Gosmer’s successor,” indicating that John Gosmer was elsewhere – presumably in Massachusetts.

John Gosmer reportedly appears in the records of Lynn, Essex, Massachusetts c1639, but I have not found that record. The Gosmers’ and Woodruffs’ time in Massachusetts was short as by 10 March 1639, the founding of Southampton, Long Island was in the works.

By December 1640, John Gosmer’s name appears on the list of parties involved in the “Indian deed” for lands that became Southhampton, Long Island, New York.

By 1644, John Gosmer was styled “gentleman” and he was a magistrate in Southampton. In 1650, John Gosmer’s only son, Richard, died. He had been appointed to the Southampton whaling squadron on 7 March 1644 from the 3rd Ward. He appears to have been born in England, but living on his own since his father was appointed to the same whaling squadron from the 2nd Ward. Whether Richard ever married and had a son is unknown.

In 1655, John Gosmer bought property in Boston, Suffolk, Massachusetts, which he deeded to his “kinswoman” Ann Carter, widow of Richard Carter in 1658. The question of how John Gosmer and Ann Carter were related has not been answered.

In 1657, John Woodruff succeeded John Gosmer in the whaling squadron, which was apparently a group of men charged with cutting up whales that drift into the shoreline. Francis Woodruff states that it was Gosmer’s stepson (who would have been 53 years old) who took his place, but John Woodruff’s son, also John, born in 1637, was certainly old enough to possibly be the new appointee.

Also in 1657, John Woodruff Sr. received a “tenement” (home) and five acres of land from John Gosmer; that deed was recorded on 20 February 1660/61, likely soon after the death of John Gosmer.

Finally, on 29 July 1659, he deeded to his “adopted son who hat lived with me from a child, all my goods and chattells, house and lands” with the consent of his wife, Elizabeth, who apparently survived him, although the date of her death is not known.

The February 1660/61 deed is the last time the Gosmer name is found in the records.

Now to continue the family sketch of John Woodruff, born c1604. By the late 1630s, John Woodruff also disappears from the Kent parish records. A list of the first settlers of Southampton, dated 1640/41 included John Gosman/Gosmer and John Woodruff.

John and Ann Woodruff had three surviving children – one son, John, and two daughters, Anne and Elizabeth. The baptism of John in Sturry, Kent on 16 April 1637 is recorded in the parish register. However, no birth/baptismal records have been found his daughters. It’s possible that they were born in Southampton.

John Woodruff wrote his will on 4 May 1670, leaving one half crowne to his son, John (the Elder) Woodruff, who became one of the founders and, by then, was living in Elizabethtown, New Jersey. Daughters Anne and Elizabeth, seemingly unmarried as no husbands or surnames were mentioned in the will, were each to receive £20 after the wife’s decease.

Years ago, I read somewhere that these two sons named John were by different wives, which makes sense to me since the Younger was born c1650 and Anne and Elizabeth were not yet married.

It’s certainly possible that John had two wives, both named Ann.

However, Francis Woodruff, in his 1908 book (cited above) that:

the peculiar and particular wording in the case of the eldest son may perhaps mean that family friction was not entirely avoided when the younger brother was adopted as son, and made heir, by the step-grandfather. [John Gosmer].

Exactly what that means isn’t clear to me. I get one John born c1637 and one born c1650. Does that mean that John the Younger was adopted and not a Woodruff by birth? Or, what I think makes more sense, is perhaps the original version I read about John having two wives, each of whom wanted a son named John.

Personally, I believe that John Gosmer’s “adopted” son was John born c1604, since he stated that John lived with him from the time he was a child and John Woodruff would have been about 7 years old when his mother married John Gosmer.

The executors of John Woodruff’s 1670 estate were John the Younger and widow Anne Woodruff.

Children of John Woodruff and Anne Ward:

1. John the Elder, baptized 11 April 1637, Sturry, Kent, England; died between 27 April 1691, when he wrote his will, and 25 May 1691, the date the will was proved, Elizabethtown, New Jersey; married probably Sarah Ogden, daughter of John Ogden of Southampton, Long Island, New York, c1659. Their daughter Sarah was born 4 January 1660/61. His will mentions wife Mary, perhaps a second marriage?
2. Anne, born c1642; died after 1670 when she is mentioned in her father’s will; reportedly married Robert Woolley [who was born 1615???] This needs more research.
3. Elizabeth, born c1644; died after 1670 when she is mentioned in her father’s will; married Mr. ____ Dayton of East Hampton, New York – ?perhaps Ralph Dayton, who settled in Elizabethtown, New Jersey. This needs more research.
4. John the Younger, born c1650, probably Southampton, New York; died between 14 January 1701, the date he made his will, and 1 April 1703, the date the will was proved, Southampton, Long island, New York; married Hannah Newton, c1675

Francis Woodruff also states that John’s daughter Anne married Robert Woolley. Something is off here, as Robert Woolley is purported to have been born in 1615, St. Albans, Hertfordshire, England.

Lacking a marriage record, is there other evidence tying John Woodruff’s daughter, Anne, to this Robert Woolley, aside from the fact that John sold his house to them?

To summarize, I believe, at this point, that John Gosmer’s adopted son was John Woodruff, born c1604 and that it is likely that that same John (born c1604) married twice with a son John born to each wife.

Can anyone add clarification to this conundrum?