HomeMy WebLinkAboutCaptain John Underhill I
John Underhill is among the few people whose family does not have deep roots in the early history of
the Town of Southold but, has remained in our local collective memory. Whether he is remembered as
being famous or infamous, depends on the individual.
Underhill lived in the town of Southold for approximately three to five years, moving here sometime
before 1656,then leaving in 1659 to make his home in the Town of Brookhaven and then in Town of
Oyster Bay.
Born between 1597 in England or 1608 in Holland (depending on which source you consult), Underhill's
family had been favored for three generations by the royals of England, until his father. John Underhill
senior(1674-1608), became involved in the Earl of Essex's rebellion against Queen Elizabeth. Realizing
that the plot had been uncovered in 1601, the family fled England for the Netherlands and joined a
group of Puritans.
In 1628, Underhill married Heylken (Helena) de Hooch and became a cadet in the guard of the Prince of
Orange.Two years later he was recruited by John Winthrop of Massachusetts Bay Colony along with
Daniel Patrick to help train the militia.'
The following year he became a freeman of the Massachusetts colony,which meant that he had the right
to vote and served in public office. He also had a say in who else could live in the area. By 1634 he had
become a Deputy(a representative) of Boston in the government, known as the General Court of
Massachusetts.2
The Europeans settlers almost as soon as they arrived had a troubled relationship with the Pequots and
their allies. Seeking to gain control of the European trade,the Pequots attempted to take control of a
Dutch trading center by ambushing and killing the Narragansetts who were on their way to trade with
the Dutch. The Dutch retaliated by seizing and holding hostage a popular Pequot Sachem Tatobem,who
they then killed. This led to the Pequots retaliating by killing a man they thought was Dutch, but turned
out to be the Englishman John Stone.'
Underhill was one of the military officers assigned the task of retaliating against the Pequots. He with
groups of soldiers that, "...burnt their houses, cut downe their corne, destroyed some of their dogges in
stead of men...,, He notes in a memoir he wrote in 1638, ransacking and setting alight Indian villages on
three separate occasions.
1636, Underhill as second in command under John Mason led the troops in the Pequot wars. The most
significant battle that he participated in was the raid against the Pequot fort in Mystic, Connecticut.
There, in his own words,
"We set on our march to surround the Fort, Captain John Mason approaching to the west end, where it
had an entrance to pass into it, myself marching to the southside,surrounding the fort,placing the
Indians for we had about three hundred of them without side of our soldiers in a ring battalia, giving a
volley of shot upon the fort... Haven given fire, we approached near to the entrance which they had
stopped full, with arms of trees, or brakes:myself approaching to the entrance found the work too heavy
for me, to draw out all those which were strongly forced in... but feeling the Fort was to Hot for us, we
devised a way how we might save ourselves and prejudice them, Captain Mason entering into a
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Wigwam, brought out afire brand, after he had wounded many in the house, then he set fire on the west
side where he entered, my self set fire on the south end with a train of powder, the fires of both meeting
in the center of the Fort blazed most terribly, and burnt all in the space of half an hour,many courageous
fellows were unwilling to come out, and fought most desperately through the palisades... many were
burnt in the Fort, both men, women, and children, others forced out, and came in troops to the Indians,
twenty and thirty at a time, which our soldiers received and entertained with the point of the sword,
down fell men, women, and children, the whose that escaped us fell into the hands of the Indians, that
were in the rear of us, it is reported by themselves, that there were about four hundred souls in this fort,
and not above five of them escaped out of our hands..Sometimes the Scripture declares women and
children must perish with their parent... We had sufficient light from the word of God for our
proceedings"'
Underhill in 1637,was then stationed in Saybrook with a force of 20 men to defend the fort from the
Dutch and the local Indians. While there he began to follow the religious teachings of John Wheelwright
and Ann Hutchinson,which were considered heresy. After signing a petition supporting Wheelwright and
Hutchinson's teachings he was removed from his post when he refused to recant his support of
Wheelwright and Hutchinson, probably seeking to avoid conflict with the colonial government he left the
New World and traveled to England.' There he wrote and published his military activities in a pamphlet
called, Newes From America.
In the summer of the following year, he came back to Massachusetts. He still supported Wheelwright
and Hutchinson, but was tolerated in the community, until he was caught having an affair with his
neighbor's wife.This led to his banishment from the Massachusetts Bay colony. Underhill along with
John Wheelwright and his other followers, moved to Dover, in what later became New Hampshire.'
Starting in 1639, Underhill's movements become difficult to trace. He starts out in Dover, elected to
government office, he styles himself as the Governor of the Exeter and Dover settlements. After his first
term, in an effort to ingratiate himself with some of the local powers, he overstepped and arrested
Gabriel Fish on charges of speaking against the king.$ Losing local support and the governor's office, he
traveled south with some followers and petitioned New Amsterdam to be allowed (as Governor
Underhill)to settle on Dutch territory.' In the same year, he also appeared in the records of the Colony of
New Haven as a freeman.10
In the following year he lost support among the people who traveled south with him, and was
summoned to Boston to answer the charges against him for his earlier adultery and heresy.11 In what
had to be a calculated move, Underhill appears in front of the Boston Court, "it was a spectacle which
caused many weeping eyes, though it afforded matter of much rejoicing to behold the power of the Lord
Jesus in his ordinances,"wrote Winthrop. "He came in his worst clothes(being accustomed to take great
pride in his bravery and neatness) without a band, in afoul linen cap pulled close to his eyes...With many
deep sighs and an abundance of tears, he "lay open is wicked course, his adultery, his hypocrisy, his
persecution of God's people here, and especially his pride.""12
He was forgiven and re-admitted into the church at Massachusetts Bay. He then moved to Stamford,
Connecticut,which was part of the New Haven Colony, before returning to New Amsterdam,were he
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leased a house and tobacco farm in Flatlands (now Brooklyn).13 Ever restless, he returned to Stamford,
where he was elected as their representative to the General Court at New Haven 14
While at Stamford, he was hired as a mercenary to work for New Amsterdam in their war against the
Lenape Indians.15 In 1644, he led troops that slaughtered and burned 120 people at Massapequa on
Long Island16,then the troop headed north and killed and burned an estimated 500 to 700 members of
the Siwanoy and Wechquaesgeek(Lenape)groups of the Wappinger Confederacy.The Dutch report of
the incident notes, "...resolved, with Serjeant Major Van Der Hill, to set fire to the huts,whereupon the
Indians tried every way to escape, not succeeding in which they returned back to the huts preferring to
perish by fire than to die by our hands. What was most wonderful that among this vast collection of
Men, Women and children, not one was heard to cry or scream" 17 For his work, Underhill was rewarded
with land on Manhattan and an island called Bergen Island.18
Needless to say,tensions were high from the friction and death toll between the Lenape and
Dutch/English communities. A Dutch man, Captain Blauvelt, after an argument with Daniel Patrick, a
founder of the community of Greenwich, shot and killed Patrick. Underhill took Blauvelt into custody
and had him incarcerated on the second floor of his house. Blauvelt was being guarded by Thomas
Stevenson and Georg Slowson, when he escaped. Stevenson and Slowson claimed that Underhill
convinced them that Blauvelt could be by himself in the upper chamber while they relaxed downstairs.19
Blauvelt was never recaptured. The following year, 1645, Underhill was elected to the governing council
of New Amsterdam.20 He became the Sheriff of Flushing sometime before 165121
The historian, Benjamin Thompson, remarks that Underhill's, "character was somewhat eccentric...
everything he did was prone to extremes.,, During the first Dutch and English War, even though
Underhill,who was probably born in Holland, married to a Dutch woman, and was living and working for
the Dutch, decided that he was pro-English. He lost his position as Sheriff when he was accused of
writing a seditious and mutinous letter, "..when some of that nation endeavored, by sinister means and
open practices, to dispossess and drive the Company wholly from that country of America, or at least to
bring its subjects there under their government. This means consisted in debauching and inciting them,
and endeavoring to seduce them from the oath they have taken and by which they were bound to the
Company,23 The letter written in 1653, rails against the government of Peter Stuyvesant and
enumerates the troubles that the Stuyvesant regime has caused or failed to solve.24
Having worn out his welcome with the Dutch, he writes to the United Colonies Commissioners offering
his services.25 Leaving New Amsterdam, he either travelled first to Providence, Rhode Island or he
established himself in Southold.
It is not known when John Underhill arrived in Southold, but he was here as of 1656. His wife Helena,
had fallen ill, and Underhill wrotes to the nearest trained medical help,John Winthrop Jr., in New
London, asking for medicine that could cure her.26 In 1658, Helen died and was the first person to be
interred in the cemetery at the First Presbyterian Church at Southold.
According to Southold Town Records, Underhill had property in the town as of 1658 and he sold that
property in 1659 to Thomas Moore.27 He then left the North Fork and moved west. Possibly settling
first in Cromwell Bay(today called Setauket).
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While in Cromwell Bay, he along with a group of residents petitions the Connecticut to join their colony.28
He married Elizabeth Feake in 1658. Feake was the daughter of Elizabeth Fones,was very well
connected to the powerful in New England. Her mother Elizbeth Fones was the widow of Henry
Winthrop,John Winthrop Sr's son and the sister-in-law of John Winthrop Jr.29
In 1661, Underhill was among the buyers of land in Brookhaven Town when Old Field was divided, he
purchased two-six acres lots.30 Around that same year he seems to have uprooted his family again to
move to Oyster Bay.31
Underhill,then appeared in testimony given in Huntington, in 1665 as a witness in a property ownership
debate and he re-enters politics, becoming the delegate to the Duke's Laws convention in Hempstead,
representing Oyster Bay.32 He also struck up a friendship with New York Governor Richard Nicolls and
was appointed the Surveyor of Customs for Long Island.33
The following year in 1666, Underhill purchased an additional three acres in Old Field.34 After complaints
by the Matinecocks over settlers encroaching on their property,the governor surprisingly appointed
John Underhill as the representative for the Matinecocks in the court case.35 Underhill also in 1666,
petitioned Governor Nicolls,to be released from having to serve in the military.36 But he did not leave
the government completely, He was appointed in 1667, by Duke of York as High Constable and
Undersheriff of North Riding of Yorkshire.37
He purchased 150 acres of land from the Matinecock tribe to the north and west of the community of
Oyster Bay in what is today, Locust Valley. In 1672 he died at his home and is buried nearby with a very
grand monument to mark his grave.
1 Capt.John Underhill Gets Un-Banished From Massachusetts Bay, 1640. New England Historical Society&
Nathaniel Shurtleff, Records of the Governor and Company of the Massachusetts Bay in New England.75.
2 Shurtleff, 116.
3 Michael Leroy Oberg, Uncas First of the Mohegans.42.
4 John Underhill, Newes From America,7,8, 15.
5 Underhill,37-39. Note: this passage has been edited with modern spelling,for easier comprehension of the
reader.
6 Shurtleff,208.
Edward Chase Jr., Early Exeter History.
s Charles Bell, History of Exeter New Hampshire, 16-17.
9 B. Fernow, Documents Relating to the History of the Early Colonial Settlements Principally on Long Island,volume
14,26.
to Charles Hoadly, Records of the Colony and Plantation of New Haven from 1638-1649, 10.
11 Shurtleff,251.
12 John Winthrop's Journal,3 Sept 1640,as quoted in Capt.John Underhill Gets Un-Banished From Massachusetts
Bay, 1640 by New England Historical Society.
13 Fernow,volume 14,36.
14 Hoadly,85.
is Benjamin Trumbull,A Complete History of Connecticut, 138-140. Underhill had the permission of the Court at
New Haven for this expedition—New Haven Colony Records, 116.
16 E.B.O'Callaghan, Documents Relative to the Colonial History of the State of New York vol 1, 186-187.
...the English under Sergeant major van der Hyl(who, a few days previously,had offered his services and was
accepted), the old soldiers under Peter Cock, all acommanded by Mr. La Montagne, to proceed hence in three
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Yachts,land in Scout's Bay on Long Island,march towards Heemstede,[Hempstead]where there is an English
Colonie dependent on us. Some who had been sent forward in advance, dexterously killed an Indians who was out
as a spy. Our force formed themselves into two divisions, Van Der Hil with fourteen English towards the smallest,
and Eighty men towards the largest village,named Mastsepe;[Dutch notation for Massapegue(Fort Neck in South
Oyster Bay, today known as Massapequa)]both were very successful,killing about one hundred and twenty men"
17 Eugene M. Boesch, Native Americans of Putnam County&Historical Society of the New York Courts,John
Underhill. Trumbull, History of Connecticut, 147. The site of the massacre is as Boesch points out is believed to be
either Pound Ridge or Bedford,both communities are just north of Greenwich and Stamford.
18 Historical Society of the New York Courts,John Underhill.
19 Hoadly, 127-128.
20 Historical Society of the New York Courts,The Eight Men (1643-1647)and the Remonstrance of the Manhatas.
zl Fernow,vol 14, 143.
zz Benjamin Thompson, History of Long Island,1839 edition,337.
zs E.B.O'Callaghan, Documents Relative to the Colonial History of the State of New York,vol II, 135-136.
14 E.B.O'Callaghan,vol II, 151.
15 David Pulsifer, Records of the Colony of New Plymouth in New England,vol 10,52.
"Josephine C. Frost, Underhill Genealogy,vol 2, 17-18. Massachusetts Historical Society Winthrop Family Paper
Microfilm reel 15 John Underhill to JW Jr 12 April 1656.
27 According to J.Wickham Case,editor of the Southold Town Records,he believes that Underhill was as resident
for one year. Southold Town Records,vol 1,75.
28 J. Hammond Trumbull, Public Records of the Colony of Connecticut 1636-1665,341.
z9 Elizabeth Fones married three times,her first husband Henry Winthrop,the son of John Winthrop Sr,governor of
the Massachusetts Bay Colony,her brother in law John Winthrop Jr,the founder and governor of New London,Ct.
Her second husband was Lt Robert Feake,who was military Lt under Captain Daniel Patrick and helped to found
Greenwich,CT. Feake,abandoned her and the family. Fone married her her last husband was William Hallet.
Without getting a divorce from Feake—but because she was so politically well connected,she was never brought
up on charges of bigamy,however the couple moved to New Amsterdam,just in case the winds of politics changed.
so Archibald C Weeks, Brookhaven Town Records vol 1, 135.
31 Frost,31.
sz Fernow,vol 14,571,565.Thompson 338.
ss Fernow,vol 14,566-567.
34 Weeks, 145.
ss Fernow,vol 14,587,589,595,629.
"Fernow,vol 14,595.
37 Frost,32.Thompson,338.The North Riding of Yorkshire is one of the many names of the Queens(and later
Nassau)Counties on Long Island during the colonial period.
Bell, Charles. 1888. History of Exeter New Hampshire. Exeter, New Hampshire: Self Published.
Boesch, Eugene J. n.d. "Native Americans of Putnam County." Web.arch ive.org. Accessed December 11,
2023.
https://web.a rch ive.org/web/20070927212443/http://www.ma hopacl i bra ry.org/local history/ad
dendum.htm.
Bond, Henry. 1860. Genealogies of the Families and Descendants of the Early Settlers of Watertown, MA.
Boston, Massachusetts: New England Historical Genealogy Society.
Chase, Edward Jr. 2016. "Early Exeter History." Exeter Historical Society. June 24. Accessed November 6,
2023. https://www.exeterhistory.org/exeter-history/2016/6/24/early-exeter-history-1638-1887.
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Courts, Historical Society of the New York. n.d. "John Underhill." Historical Society of the New York
Courts. Accessed December 11, 2023. history.nycourts.gov/figure/john-underhill/.
Cox,John Jr. 1916. Oyster Bay Town Records volume 1. New York, New York:Tobias Wright.
Fernow, B. 1883. Documents Relating to the History of the Early Colonial Settlements Principally onLong
Island. Albany, New York:Weed, Parsons and Company.
Frost,Josephine C. ed. 1932. Underhill Genealogy. Brooklyn, New York: Myron C.Taylor for the Underhill
Society.
Hoadly, Charles J. 1857. Records of the Colony and Plantation of New-Haven From 1638-1649. New
Haven, Connecticut: Case,Tiffany and Company.
Macy, Harry Jr. 2002. "Captain John Underhill." Underhill Society of America. Accessed November 6,
2023. https://underhillsociety.org/cpage.php?pt=15.
Oberg, Michael Leroy. 2003. Uncas First of the the Mohegans. Ithaca, New York: Cornell University Press.
O'Callaghan, E.B. 1853. Documents Relative to the Colonial History of the State of New York Procured in
Holland, England and France vol 1. Albany, New York:Weed, Parsons and Company.
—. 1858. Documents Relative to the Colonial History of the State of New York vol 2. Albany, New York:
Weed, Parsons and Company.
Pulsifer, David ed. 1859. Records of the Colony of New Plymouth in New England volume 10. Boston,
Massachusetts:William White by order of Legislature of the Commonwealth of Massachusetts.
Shurtleff, Nathaniel B. 1853. Records of the Governor and Company of the Massachusetts Bay in New
England. Boston: Massachusetts Commonwealth.
Society, New England Historical. 2022. "Capt.John Underhill Gets Un-Banished From Massachusetts Bay,
1640." New England Historical Society. Accessed November 6, 2023.
https://newenglandhistoricalsociety.com/?s=John+Underhill+.
n.d. "The Eight Men (1643-1647) and the Remonstrance of he Manhatas." Historical Society of the New
York Courts. Accessed December 11, 2023. https://history.nycourts.gov/about_period/eight-
men/.
Thompson, Benjamin. 1839. History of Long Island. New York, New York: E. French.
Trumbull,J. Hammond. 1850. The Public Records of the Colony of Connecticut. Hartford, Connecticut:
Brown & Parsons.
Underhill,John. 1638. Newes From America. London, UK:JD for Peter Cole.
—. 1656. "Winthrop Family Papers ." Letter John Underhill to John Winthrop Jr. Unpublished,
Massachusetts Historical Society Winthrop Family Papers Microfilm,April 12.
Weeks,Archibald C. 1924. Brookhaven Town Records vol 1. New York, New York:Tobias A Wright.
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