I notice that several surnames on the list of free African Americans of Winchester, VA are shared by members of related families, including:

JACKSON
Manuel

JENKINS
John, laborer, Cameron
Lucky, spinster
(This family possibly is related to James Jenkins, father of Josephine Jenkins who married Reuben Strange, a son of Richard and Sarah Strange of Winchester, VA)

JORDAN
Sylvester
Lewis
Warner
Baylor

LEONARD
Moses (husband of Courtney, daughter of Reuben Strange)

ROBINSON
Charles, waiter, Loudoun County
Ginny
Jenny (wife of Charles), William Stell's
Polly, washerwoman, Kent
Robert
Edg (Edgar?)

SMITH
George
Milley, spinster, Kent

STRAGE (STRANGE)
Richard (husband of Sarah; son of Reuben Strange, FPOC in 1817)

WALLS
Caty/Catherine, spinster, Cameron
Ann, spinster, Cameron
(Moses Leonard & Courtney Strange were married Dec. 1827 by James Walls)
*
STRANGE // Marriages of African Americans in Clarke County VA record books:

Reuben & Betsie Strange: parents of John, born c. 1837
John & Jane Strange: parents of James, born c. 1843; Stephen, born c. 1848
John & Cloe (Chloe) Strange: parents of Reuben, born c. 1856
Macklin & Evalina Williams: parents of Clara, born c. 1843 (Could be misprint for Cloe/Chloe?)
James & Ann Smith: parents of Helen, born c. 1846
Edward & Sallie Williams: parents of Millia A., born c. 1849; Catherine born c. 1862
Henry & Louisa Robinson: parents of Delilah, born c. 1853

John 30, widower black, Clarke Co., VA Farm Hand, parents Reuben & Betsie Strange, married 13 Jan 1867 to Clara Williams, 24, single, black, Clarke Co., parents Macklin & Evalina Williams, Af-Am. (John Strange born circa 1837; Clara Williams born circa 1843—could be misprint for Cloe/Chloe?)
*
James, 21 widower, black, Clarke Co., Farm Hand, parents John & Jane Strange, m 5 Oct 1867 to Helen Smith, 21, widow, black, Clarke Co., parents James & Ann Smith (Different surname not given), Af-Am. [James Strange & Helen Smith born circa 1846]
*
Stephen, 22 widower, black, Clarke Co., Farm Hand, parents John & Jane Strange, married 29 Oct 1870 to Millia A. Williams, 21 single, black, Clarke Co., parents Edward & Sallie Williams, Af-Am couple. [Stephen Strange born circa 1848; Millia A. Williams 1849]
*
Stephen, 22 widower, black, Clarke Co., Farm Hand, parents John & Jane Strange, married 29 Oct 1870 to Millia A. Williams, 21 single black, Clarke Co., parents Edward & Sallie Williams, Af-Am couple. [Stephen Strange born circa 1848; Millia A. Williams 1849]
*
Reuben, 23, single, black, Clarke Co., Farm Hand, parents John & Cloe (Chloe) Strange, married 14 Aug 1879 in White Post, Clarke Co., to Catherine Williams 17, single, black, Clarke Co., parents Edward & Sallie Williams, Af-Am [Reuben born circa 1856; Catherine 1862]