Individual Details

John is said to have immigrated to America in 1727 aboard the ship "Eagle's Wing" which docked at New Castle, Delaware. He came with his wife, four sons and a daughter. His three married sisters and their husbands came on the same ship - Elizabeth & James Moor, Jane & Alexander Ritchey, and Catherine & John Dudgeon.
The families went first to Lancaster Co PA to Chestnut Level. In approximately 1738 they moved to Lunenburg Co VA, the "Caldwell Settlement" where John founded the Cub Creek Presbyterian Church. John and son William were among the Justices of the Peace in Lunenburg.

http://www.concentric.net/~pvb/GEN/jvres.html
The founders of the Caldwell Presbyterian Settlement arrived at New Castle, DE in 1727 on a ship named the Eagle's Wing or the Eagle Wing, and it had apparently been a ship that made regular trips to New Castle aver the period from about 1717 to 1750 or so, carrying mainly Scots-Irish immigrants, however no records of its passenger lists have been found.

Two of the sons shown - Robert and James were born many years after the others. Since they are apparently named in John's will - perhaps they had a younger mother, although no wife was living at the time John died, and John does refer to minor children.

Lunenberg Tax list of 1748 by William Caldwell includes John, James, David Caldwell and himself.
In 1749, there was James, James Jr., John, David, William, and a John Caldwell on the Dan River.
1750: David, James & James Jr., William, Henry, John & John Jr.

http://files.usgwarchives.net/va/lunenburg/deeds/deedbk01.txt
WILL OF JOHN CALDWELL
Presented at the court continued and held for Lunenburg County, Virginia, the
third day of April, 1751.
In the name of our Eternal and Almighty God, who formed the Universe by the Word of his power, and governs it by the dictates of His wisdom, I, John Caldwell, of Cub Creek in Virginia, being in health of Body, sound Memory and full of tranquility, for which I adore the divine goodness of God, however, not knowing how soon or how suddenly my change may come, I ordain and declare this to be my last Will and Testament.
In the first place, I must humbly resign my Immortal Spirit into the hands of my most
Merciful Creator, beseeching him to receive it into the number of his Elect through the merits of Jesus Christ. Then, as for my perishing Body, I entrust it may be committed to its kindred earth without pomp or needless expense, with a firm persuasion that my Redeemer lives and shall stand on earth at the last Day I most earnestly recommend my fatherless children to the care of the most Merciful Providence of God, to guard them from the wiles of the crafty and the oppression of the powerful and so to direct the conduct of their lives that they receive to themselves his everlasting blessing and protection then as for the Estate with which it hath pleased God to Bless me, by His permission, I dispose thereof in the following manner:
(1st) My firm intention is that the few debts which may be owing at the time of my death, be punctually paid and speedily discharged, and as I have taken an honest care in my lifetime topay all that were considerable, I desire that no appraisement be made but an
Inventory taken of all my Personal Estate and left in the power of my Executor for the use and the support of my children that shall be under age at my decease.
Imprimis I leave and bequeath unto my oldest son, William Caldwell, four hundred acres of land whereon he now lives with all the improvement thereunto belonging to him and his heirs forever, and also twelve pounds ten shillings in cash, and also my great Bible.
I also leave and bequeath to my son, John Caldwell, four hundred acres of land
known by the name of Flag Spring, and I empower my Executor to sell and make a
title to said land for the use of John Caldwell, as said Executor thinks proper. I likewise leave and bequeath to my son, John Caldwell, one hundred acres of land where my Mill now stands, together with the Mill and all improvements thereunto, to be let, rented or sold at the discretion of my executor for the use of said John Caldwell.
I also leave and bequeath to my son James Caldwell, five hundred acres of land whereon I now live, with all improvement thereunto, belonging to him and his heirs forever.
I also leave and bequeath to my son, David Caldwell, five hundred acres of land lying on the east side of Cub Creek, being part of one thousand and eight acres by estimation more or less, being part of the aforementioned one thousand and eight acres, beginning at the mouth of Lawes Creek, then up Cub for quantity, to him and his heirs forever.
I also leave and bequeath to my son Robert Caldwell, six hundred acres of land lying on the West side of Cub Creek, part of it being of the aforementioned one thousand and eighty acres, and the remainder being three hundred acres adjoining the aforesaid land
lying on Walkers Branch, to him and his heirs forever.
I also order and impower my Executor to sell and title the remainder of the aforesaid thousand and eighty acres of land lying above the mouth of Walkers Branch adjoining John S_____(Short?), for the use and support of my children that shall be under age
at the time of my death.
I also leave and bequeath to my three sons, Viz: John, Robert and James Caldwell, all my horses, geldings, mares and colts, to be divided amongst them at the discretion of my executor, and for the due performance of this my last will and testament, I hereby appoint
and ordain my son, David Caldwell, my executor and guardian of as many of my children as shall be under age at the time of my death, and last of all, I hereby revoke all former
wills by me made at any time, and do declare and ordain this to be my last will and testament.
Witness my hand and seal this 26th day of November in the year of our Lord one
thousand seven hundred and forty eight.'
Signed, John Caldwell
Witnesses Present:
William Rogers
George Moore
John McNeese

At a court continued and held for Lunenburg County the third day of April, 1751
The within written last will and testament of John Caldwell, deceased, was exhibited in Court by David Caldwell, Executor, therein made oath thereto according to law and the same was proven by oaths of all the witnesses thereto and ordered to be recorded, and on the motion of the said executor who have first together with sureties, entered into bond and acknowledge same. Certificate was granted him for obtaining a probate of the
said will in due form.
Teste: Clement Reed, C.L.C.
Truly recorded Teste: Clement Reed
Recorded Deed Book 1, pages 498-499
A copy Teste:
W.R. Moore, Clerk
Lunenburg County Circuit Court
by Grace I Marshall, Deputy Clerk
(Typist note: This was a certified typed copy of the will.)

http://files.usgwarchives.net/va/charlotte/church/cubcreekhist.txt
The first log structure was known as the Caldwell Meeting House and was probably
erected shortly after John Caldwell led a group of Scotch Irish to "the back parts of
Virginia" and established the Caldwell Community on Cub Creek around 1738.

In late 1727, John Caldwell, his wife and five children, landed at Newcastle in the
Colony of Delaware, a part of "a considerable exodus of Scotch Presbyterians
from Ulster County, Ireland. Looking for religious freedom and for exemption of
taxation for the support of the Established Church."

Finding the choicest locations in Pennsylvania already occupied they moved on
to Virginia and when the Act of Toleration was passed in 1738 they were in Albemarle
County, Virginia, having removed there about 1733. On May 26, 1738, John
Caldwell appeared before the Philadelphia Synod of the Presbyterian Church, asking
the Synod to officially ask the government to ensure frontiersmen the right to worship
as they pleased as there were a large group of Presbyterians planning to settle in the
back parts of Virginia.

On May 30th, such a letter "To the Honorable William Gooch, Esquire, Lieutenant
Governor of the Province of Virginia" was approved by the Synod, and James
Anderson carried the letter to Williamsburg and received a favorable reply from
Governor Gooch. There is evidence to suggest the occupation of the land was
under way when Governor Gooch's reply was communicated to the Synod at their
session in 1739. The Caldwell Settlement occupied an area of about 5 or 6
square miles on Cub, Wallace and Turnip Creeks and was bounded on the south
by the Staunton River.

Find A Grave Memorial# 13410344. Said buried Cub Creek Cemetery, Charlotte Co VA. Probably traditional as stones seem to be fieldstones.

From Boyle Co KY Website:
John Caldwell, the immigrating ancestor of the Caldwell family in Boyle County, was born 9 January 1683 in Lifford Parish, Ballyoogan, County Donegal, Ireland. His ancestry can be traced back at least five generations to Alexander Caldwell, who immigrated from Scotland to Ireland before 1600. The immigrant John married Margarette Phillips and they are the parents of Margaret Amey Caldwell, wife of James Mitchell, Sr. mentioned in another section of this program. John and Margarette Phillips Caldwell eventually made their home in the Cub Creek area of Lunenburg County, Virginia, where John, his son David, and grandson Robert were ruling elders in the Cub Creek Presbyterian Church. [Cub Creek Presbyterian Church and Congregation 1738-1838, Elizabeth Venable Gaines, page 33] John Caldwell of Scotch ancestry, but of Irish birth emigrated from Antrim, Ireland around 1727, and settled first at Chestnut Level, Lancaster Co., PA and later removed to Charlotte County, Virginia.
The seven children of John and Margarette Phillips Caldwell were:
(1) Captain William Caldwell, born in Ireland and died at Cub Creek, Lunenburg County, Virginia. Captain William married Rebecca Walkup Parks in Ireland and served as a major in the French and Indian War. He was a large land owner and planter in the Lunenburg County, Virginia area.
(2) Thomas Caldwell, born 1706 in Ireland, died at Cub Creek, now Charlotte County, Virginia, in March 1765. Thomas married Mary Jane Parks in Ireland.
(3) David Caldwell, born in 1709 in County Donegal, Ireland, and died in Cub Creek. David married Mary Dudgeon about 1736 in Mercer County, Kentucky, the daughter of John Dudgeon and Catherine Caldwell. His wife died about 1820 at Caldwell’s Station, Mercer County, Kentucky. David’s will set aside 10 acres for use of a Presbyterian Meeting House called “Meeting House Land” which became the site of the Cub Creek Presbyterian Church. This was the first Presbyterian congregation in Virginia south of the James River. After David died his wife moved with her children to Kentucky. Part of her family settled in Adair County, KY.
(4) Mar garet Amey Caldwell – her story is told in the Mitchell section of this program
(5) John Caldwell, Jr. was born in Ireland and died in Tennessee. He married Margaret Eleanor Ewing and after her death in 1745 married Jane Kennedy.
(6) Robert Caldwell, born in 1731 in Lancaster County, Pennsylvania, died in July 1806 in Mercer County, Kentucky. This Robert was the founder of Caldwell’s Station on Town Fork of Salt River, between Perryville Road and Lebanon Road about 5 miles from Danville in Mercer County (now Boyle) in Kentucky. He married Mary Logan, daughter of David Logan and Martha Dudgeon. Robert and Samuel McDowell represented the Concord (Danville) Presbyterian Church at the very first Presbyterian Conference in Kentucky, held at Cane Run Meeting House near Harrodsburg on 12 July 1785.
Note: There is a James that was a son as named in John's will but the residence of this James makes me think that the following James Caldwell was misplaced and does not belong in this family:
(7) Reverend James Caldwell served as a Chaplain in the New Jersey Brigade and was known as the “Fighting Parson”. He actively secured rations and supplies for the troops and was made Deputy Quartermaster General in the Quartermaster Corps. In 1780 his church and home were burned by Tories. His wife went to Connecticut Farms, New Jersey, but was shot and killed with her baby in her arms through the window by German mercenaries. James Caldwell was shot in Elizabethport, NJ by James Morgan in a dispute over a package that Morgan wanted to examine. Morgan was convicted of Caldwell’s murder in January 1782.

John's granddaughter, Martha Caldwell married Patrick Calhoun and was the mother of John Caldwell Calhoun, the leading statesman and well-known Senator from the South." [Historical and Biographical Sketch of the Caldwell Family, Page 20-21] Other prominent descendants are General Samuel Caldwell, Colonel of Kentucky Troops in 1812, attorney, and first clerk of Logan County, Russellville, KY; Elias Boudinot Caldwell, clerk of the US Supreme Court for 25 years; a number of ministers and several wives of governors.
It is through the influence of the Caldwells and some of the other families who lived in the Cub Creek area of Virginia that Dr. David Rice came to the Danville area to be the pastor of the Presbyterian Church. According to Calvin Morgan Fackler’s book A Chronicle of The Old First Presbyterian Church, Danville, Kentucky, Rice had been in the Cub Creek area serving as a pastor there from 1767-1771. James Mitchell, Rice’s son-in-law had already come to Kentucky first; he may have come to reaffirm for David Rice the credit of establishing a Presbyterian Church here. Documents show that this meeting house, built on the town square, was the first in the west.

Birth	1683	Lifford Parish, Ballyoogan, Donegal, Ireland
Marriage	4 Jan 1702/03	Lifford Parish, Ballyoogan, Donegal, Ireland - Margaret Phillips
Death	6 Oct 1750	Lunenburg County, Virginia
Burial		Cub Creek Cemetery, Charlotte County, Virginia

Spouse	Margaret Phillips (1685 - 1748)
Child	William Findley CALDWELL (1704 - 1761)
Child	Thomas CALDWELL (1706 - 1747)
Child	David CALDWELL (1709 - 1765)
Child	Margaret CALDWELL (1712 - 1750)
Child	John CALDWELL (1715 - )
Child	ROBERT CALDWELL (1732 - 1806)
Child	Living

Father	Joseph Caldwell (1656 - 1730)
Mother	Jane McGhie (1661 - )
Sibling	Catherine Caldwell (1691 - )