by Ronny O. Bodine


The following article was first published in
the December 1999 issue of the
Owsley Family Historical Society Newsletter.

Among the many families that have married into the Owsleys, probably none other is as well known as the Middletons. When Thomas Owsley and Mary Middleton married about 1746, they established a family that made a significant impact on the history of Kentucky. This account draws upon a number of previously published histories and presents the immediate ancestory of Mary Middleton Owsley in compact form. Readers are invited to obtain copies of cited references found in the bibliography at the end of this article.

1. ROBERT MIDDLETON, the immigrant ancestor, was transported to Maryland, along with Benjamin Arnold and Thomas Thornton, by Benjamin Rozer of Charles County, Maryland prior to 16 Feb 1671. Born c1651 (being aged 'about 30' in a deposition filed Aug 1681), he died shortly before 6 May 1708 in Prince George's County, Maryland when Mary Middleton and John Middleton signed the bond to administer his estate. In 1681 the Council at St. Mary's City commissioned him a coronet in the Mounted Troops under Captain Randolph Brandt. In 1696 he was appointed a justice and also a coroner for Prince George's County. From 1704-1708 he was a warden and vestryman of St. John's Church of Piscataway Parish at Broad Creek. He secured his first land in 1679, being a 112 acre tract called "Wickham." He was married in 1672 to Mary Wheeler, daughter of Major John Wheeler and his wife Mary. John Wheeler gave to Robert and Mary Middleton "for fatherly love and natural affections" his 365 acre plantation "Wheeler's Hope." Besides the five known sons, there may have been others and surely daughters as well.

     a. Capt. John Middleton, born c1673, he died before 1750, probably in Fairfax County, Virginia to which place he had moved about 1741. He was married c1695 to Mary. Court records repeatedly refer to him as 'Captain' supporting the belief he had a militia commission, probably in the Prince George's Rangers. He was elected vestryman of St. John's Church of Piscataway Parish in 1707. As principal heir, he inherited his father's entire estate and established his seat on the family estate of "Wheeler's Hope."

     b. James Middleton, born c1675 in Charles County, Maryland; died there shortly before 6 Oct 1769 when his will of 5 Aug 1769 was proved. He married Sarah, daughter of John Smith, who survived him.

     c. Thomas Middleton. See 2, following.

     d. Robert Middleton, born c1682 in Charles County, Maryland; died probably about 1729. He was married to Elizabeth Smith.

     e. William Middleton, born c1686 in Charles County, Maryland; died shortly before 15 Nov 1769 when his will of 15 May 1769 was proved in Charles County. From 1732 to 1741 and again in 1748 he represented Charles County in the General Assembly and from 1739 to 1747 served as a Justice of the Peace. He was married (1) c1712 to Elizabeth Tears, widow of John Keech, and daughter of Rev. Hugh and Ruth (Wynne, Wine) Tear. She was living 16 July 1748 but was deceased by 30 Aug 1758. By the latter date he was married (2) to Henrietta.

2. THOMAS MIDDLETON was born 1676-8 in Charles County, Maryland. He died shortly before 4 Jan 1745 when his estate was appraised. He was married (1) c1702 to Penelope, daughter of William and Mary Hatton. Her parents left portions of their respective estates to her children. He married (2) 1735 the widow Alice Smallwood, who died soon after their marriage. He married (3) 1735/6 to Susanna Brett, widow of George Brett. Thomas Middleton was appointed Captain of Rangers of Prince George's County in 1698 and served as parish vestryman 1706-1733. All of his children were born of his first wife.

     a. Mary Middleton, married by 1729, William Hawkins, to whom her father "for love and affection" deeded "Long Point" comprising 60 acres in Prince George's County, Maryland.

     b. Hatton Middleton, born 9 Dec 1705 in St. John's Piscataway Parish; died shortly before 1 Jun 1733 when the estate administration bond of his widow was filed in Prince George's County, Maryland. Before 1731 he married Jane. She died shortly before 20 Feb 1769 when her will was proved in Prince George's County.

     c. Thomas Middleton. See 3, following.

     d. Benjamin Middleton, born 24 Feb 1709/10.

     e. Penelope Weston Middleton, born 29 Mar 1712.

     f. Sarah Middleton.

     g. Elizabeth Middleton.

     h. Eleanor Middleton.

     i. Susannah Middleton.

The four youngest daughters were all unmarried and under age on 25 Mar 1735 when their grandmother's inheritance was delivered to their guardians.

3. THOMAS MIDDLETON was born 29 Jan 1707/8 in Prince George's County, Maryland. In 1745 he approved the inventory of his father's estate and shortly afterwards settled in Fairfax County, Virginia. In 1763 he was one of the purchasers at the estate sale of William Owsley, of Loudoun County, Virginia and was living in 1776 in Prince George’s County, Maryland when he gave a deposition declaring his age as 67.  He is said to have been married c1729 to Ann Bayne, though evidence appears based solely upon family tradition and that a granddaughter, Ann Bayne Owsley (1747- 1792) bore the name.

     a. Mary Middleton. See 4, following.

     b. Thomas Middleton. Died 1809 in Kentucky. Married to Nancy.

     c. Hatton Middleton, for service as a Captain in the Georgia Militia during the Revolutionary War he was awarded a 575 acre bounty land warrant in 1784.

     d. Benjamin Middleton.

     e. Walter Middleton. In a deed of 8 Aug 1766, he refers to himself as late of Prince George's County, Maryland and now of Loudoun County, Virginia, and as a grandson of Thomas Middleton. (Loudoun Co. Deeds E: 235-6). Apparently married to Elizabeth Chadwell, he may be identical with the Walter Middleton who appears on the 1795 tax list of Lincoln County, Kentucky.

     f. Sarah Middleton.

     g. Henry Middleton, married Nancy Ann Owsley (1772-1817), daughter of William Owsley.

4. MARY MIDDLETON. Born 1730 in Virginia, she died 16 Sep 1808 on the family plantation in Garrard County, Kentucky. In 1746 she was married to Thomas Owsley. Thomas was born 1731-2 in Prince William County, Virginia and died 1 Nov 1796 in Madison County, Kentucky.



Herndon, John Goodwin. Robert Middleton of Charles and Prince Georges Counties, Maryland and Numerous Descendants of His. Haverford, PA, 1954.

Lloyd, Daniel B. The Middletons and Kindred Families of Southern Maryland. Bethesda, MD, 1975.

Taylor, Jamie Kay Kemp, ed. Middleton Family Newsletter. 1994- . 210 Avenue M., Abernathy, TX 79311. E-mail

Semmes, Raphael Thomas. The Semmes and Allied Families. Baltimore, 1918.

Smith, Elizabeth Wiley. The History of Hancock County, Georgia. II: Ancestors, Families, and Genealogies. Wilkes Pub. Co.: Washington, GA, 1974.