Fourth Generation Inclusive

Historical Documents of Genealogical Interest to Researchers of North Carolina's Free People of Color

Tag: Winn

Political Register.


County Officers. …

Commissioners – E.B. Jordan, Washington Winn, J.K. Smith, N.G. Holland

Justices of the Peace. …

Geo. W. Simmons. Date of Qualification, Aug. 30th, 1873. Post Office Address, Dudley.

The Legislative Manual and Political Register of the State of North Carolina for the Year 1874. Raleigh (1874).

In the 1860 census of Buck Swamp, Wayne County: Washington Winn, 35, carpenter, wife Temperance J., and children Aaron, 17, Levi, 15, Elizabeth, 13, James, 11, and Giles, 9.

They are very well known.

$200 Reward. Ranaway from the subscriber, on the 22nd inst., FOUR NEGRO BOYS, named as follows: CHARLES WINN, aged about 24; WILLIAM, aged about 17 years; JOHN, aged 14 years; JIM, aged about 12 years.

The above boys are very well known as the children of Adam Winn. I think they intend trying to get to some free state. The above reward will be given for their delivery, or for their confinement in any jail in the State.   THOMAS BENNETT. Mt. Olive, Wayne co., July 25, 1854.

Fayetteville Observer, 3 August 1854.

[Sidenote: Adam Winn was a free man. Several of his sons were slaves. — LYH]

Levi & Betsy Winn.

Image LEVI WINN was probably born in northern Duplin County. Elizabeth, called “Betsy,” last name unknown, was his second wife. They are buried at First Congregational Church in Dudley, Wayne County.

Photo by Lisa Y. Henderson, March 2013.

In the 1860 census of Buck Swamp, Wayne County: Levi Winn, 47, blacksmith, wife Elizabeth, 39, and children Henry, 21, David, 20, Pinkney, 19, George, 17, Charles, 15, Mary, 13, Martha, 11, John, 9, Elizabeth, 7, Susan, 5, and Levi, 3.

Near the blacksmith shop on the old road.

I, Thomas Hollowell, of the County of Wayne and the State of North Carolina being in feeble health but of sound mind and memory do make this my last will and testament in manner and form as follows: First – I give to my wife all my household and kitchen furniture, my buggie and harness also I have one note I hold against John Hollowell in the hands of my executors for them to pay to her the amount of interest so long as she may live. My will further is that my two sons Jesse and Thomas shall furnish my wife a bountiful support and in case they shall refuse at any time, I wish for her to have a dower laid off on the lands I leave them. Second – I give to my Levi Hollowell two notes that I hold against him. Item 3rd – I give to my granddaughter Elizabeth A. Stanton one note that I hold against her brother Thomas H. Stanton. Item 4th – I give to my grandson Levi H. Massey one acre of land joining Dudley on the south side of the old road near Levi Winn‘s blacksmith shop. Item 5th – I give to my son John Hollowell two shares in the Wilmington and Weldon Railroad Company. Item 6th – I give to my son Jesse Hollowell all the land I own lying on the east side of my Gin Branch also the upper part in the Big Fork down to where the bend of the Branch comes nearest together, and then down the run of Big Fork to the head of the Gin Branch and then to extend down the Canal to the run of Brook’s Swamp except the privilege of enough land near the Gin House at the end of the Gin Dam to put up a cotton screw also two shares in the Wilmington and Weldon Railroad Company, also two lots in Dudley known as No. 5 and No. 15. Item 7th – I give to my son Thomas L. Hollowell all the land I own on the west side of said Gin Branch from the line marked out for Jesse Hollowell to the aforesaid Brook’s Swamp also one share in the Wilmington and Weldon Railroad Company, two lots in Dudley known as No. 13 and 14, and one note that I hold against the said Thomas L. Hollowell. Item 8th – I wish my executors hereafter named to pay all of my just debts out of my estate not heretofore named and given away. Item 9th – My will and desire is that the balance of the amount due my estate in John Hollowell’s hands after paying the interest to my wife during her life and the balance of my estate after paying my debts to be equally divided between my living children and to those deceased to the heirs of their body. Lastly – I constitute and appoint my son John Hollowell and my grandson Levi H. Massey Executors to this my last will and testament hereby revoking all other wills by me made this 25th of 10th month A.D. 1861. Thomas Hollowell. Sealed in the presence of – Mary E. Hollowell, Jesse T. Hollowell.

Proved November Term 1865.

Book R14, Page 239, Wayne County Superior Court Clerk’s Office, Wayne County Courthouse.

Where Thunder Swamp Branch crosses the main road.

Adam Winn to Lemuel Cherry

State of North Carolina, Duplin County   }         This indenture made this 30th of July 1841 Between Adam Winn of the one part and Lemuel Cherry of the other part and both of the same State and County witness that I the said Adam Winn for and in consideration of the sum of twelve dollars to him in hand paid by Lemuel Cherry before the sealing and delivery of these presents the receipt whereof is hereby acknowledged hath given  granted bargained and sold do by these presents bargain sell and make over unto him the said Lemuel Cherry his heirs executors Administrators & assigns forever a certain ankerage or tract of land lying and being in the County of Duplin and on the waters of thunder swamp it being part of the land that Adam Winn bought of Lucy Win and part of the old Jonson tract of land and I the said Adam Winn doth assign over to the said Lemuel Cherry all the right title interest or claim in the before mentioned land containing ten acres more or less and begins and runs as follows (viz) Begins on main road that runs in Wayne and where thunder swamp branch crosses the main road an runs up said road to a large pine and then corners a new made corner and then runs a strait line of marked trees to William L. Hills line and then with Hills line to said Cherrys line then down said Cherrys line to the beginning and I the said Adam Winn doth my heirs executors & admrs or assigns no warrant and defend the before mentioned lands unto him the said Lemuel Cherry his heirs executors admrs or assigns forever against all other person or persons whatsoever laying any claim to the same in witness whereof I the said Adam Winn have hereunto set my hand and seal the day and date first above written signed sealed and delivered in the presence of Kenan Millard and Wm P. Cherry   Adam Winn (seal)

North Carolina, Duplin County Court January term 1852

The due execution of the foregoing deed is proved in open Court by the acknowledgement of Adam Winn the bargainor and ordered to be registered.  B.F. Grady Clk

Grantor Book 20, Page 407, Duplin County Register of Deeds Office, Duplin County Courthouse.

In the 1850 census of North Division, Duplin County: Adam Winn, 45, farmer, with William, 13, Marshal, 11, John, 9, Woodard, 7, Woodley Winn, 5, plus Moses Simmons, 18. Adam reported $3800 in real property.  [Sidenote: Lemuel Cherry, 71, white, farmer, is listed four households away from Adam Winn in this census. His household included Elender Young, 50, who was white. Elender Young was likely the mother of America Young, who married Adam Winn’s brother Charles Winn.  Also, though Adam’s sons are listed as free, they were in fact his own slaves. More about that later. — LYH]

Sarah “Sallie” Greenfield Winn.


SARAH GREENFIELD WINN was born about 1820, probably in southeast Wayne County.  She married Gray Winn about 1835 and was widowed in 1850.  Their children were Elizabeth Winn Simmons, Edward James Winn, Eliza Winn, Penny Winn Simmons, Ally Winn and Washington Francis Winn. She died in 1909 and is buried near her son Edward in a small family graveyard near Dudley in Wayne County.

Photograph by Lisa Y. Henderson, March 2013.

In the 1850 census of South Side of the Neuse, Wayne County: Sally Winn, 30, and children Betsey, 14, Edw’d J., 12, Eliza, 10, Penny, 6, Ally, 4, and Washington, 1.

Where are they now?: No. 20.

T.W. was born in North Carolina in the 1940s. He is descended from the following free people of color, all of Robeson County, unless otherwise noted:

(1) Keziah Brooks [1815-1893]

(2) Hugh Chavis [1807-1862] via Effie Ann Chavis [1827-1917]

(3) Matilda Jones

(4) Mackie Jane Locklear [1845-??]

(5) Richmond Locklear via Anna Eliza Locklear [1840-??]

(6) Thomas Locklear [1780-ca1865] via Thomas Locklear [1828-1892] via Nicholas Locklear (ca1845-??)

(7) William Maynor [1805-ca1880] via Angus Maynor [1832-ca1890] via Jordan Riles Maynor [1860-1941]

(8) Bryant Oxendine [1838-ca1875]

(9) Solomon Oxendine [1831-1897] via Martha Oxendine [1862-??]

(10) Clarissa Sweat [1814-1897]

(11) Emily Terry [1848-1919, Cumberland/Wayne]

(12) Charles Winn [1817-1892, Duplin/Wayne] via William Winn [1835-??, Wayne/Robeson]

(13) Martin Woodell via Patsey Woodell [1837-1880]

(14) Elender Young [1800-ca1865, Duplin/Wayne] via America Young [1820-1900, Duplin/Wayne]

William & Pennie Winn Simmons.

ImageWILLIAM and PENNIE WINN SIMMONS. William Simmons was born about 1837 in Sampson County to James Simmons and Winnie Medlin Simmons.  Pennie Winn, born about 1844, probably in Wayne County, was the daughter of Gray Winn and Sallie Greenfield Winn.

In the 1850 census of Northern District, Sampson County: James Simmons, 52, ditcher, wife Winney, 40, and children Nancy, 17, Bryant, 15, William, 13, and Martha, 11.

In the 1850 census of South Side of the Neuse, Wayne County: Sally Winn, 30, and children Betsey, 14, Edw’d J., 12, Eliza, 10, Penny, 6, Ally, 4, and Washington, 1.

5 chears, one cubbard, 3 bee gumes.

“Account of the Sale of the property of Matthew Aldridg Deceased sold by Joseph Hollowell Adm. on a credit of six months, Nov 20th 1868”

His widow [Catherine Boseman (or Simmons) Aldridge] purchased five “chears”, cart wheels and an axle, two tables (one small), two beds and furniture, “one cubbard & contents,” a clock, a gun, “3 Bee Gumes & work bench,” a tub dipper, kitchen furniture, a blind mare and two beehives.  Green Simmons, George Simmons and David Winn purchased tools, and “Robbert Aldridg,” who likely was Matthew Aldridge’s brother, bought the fourth and fifth beehive choices.  A note on William Carter for a $27.50 debt, due 1 January 1869, was described as doubtful.  The Application for Letters of Administration in the file notes that Aldridge’s heirs were John Henry Aldridge, Wm. Aldridge, Frances Aldridge, Della Aldridge, Mary Ann Aldridge, Joanna Aldridge, and James Thomas Aldridge.

In the 1860 census of Buck Swamp, Wayne County: Matthew Aldridge, 50, wife Catharine, 28, and children William, 10, John H., 16, Frances, 7, Delia, 3, and Mary A., 1, with James Boseman, 26.  All the Aldridges described as mulatto, and Matthew and James worked as railroad hands.  Matthew reported owning $200 real estate and $25 personal property.

Estate Records, Wayne County Records, North Carolina State Archives; US Federal Population Schedules.


We promise to pay.

On demand the first day of January 1848 we or Either of us do promise to pay John Lewis the Admr for ayres of urban Lewis decd it being for the sum of thirty dollars and fifty cents it for Rent of the land belonging to M. Husted lying on the East side of the Railroad joining James Kelly this January 29th 1847 test Obed Brock             Gray X Winn, Levi Winn, Adam X Greenfield

Estate Records, Wayne County Records, North Carolina State Archives.

[Side note: Urban Lewis (1788-1846) was my great-great-great-great-great-grandfather. — LYH]