This is an amazing story of enslavement, emancipation and independence throughout the 19th century and continuing through the Reconstruction era.  Isaac was born into slavery in 1818.  His mother was an unknown enslaved woman and his father, Josiah Holleman, was a white landowner in western Isle of Wight County near the Blackwater River, where Surry, Southampton, and Isle of Wight counties meet.  Isaac later met and fathered three children with Malinda Pretlow, a Free Negro.  By 1836 his enslaver and father, Josiah, applied to the court for Isaac’s emancipation.

Josiah continued to enslave others, and about a decade later when Josiah made his will, he referred to Isaac as enslaved. Josiah died shortly afterwards, and the estate executor sold Isaac for $355 to Richard Urquhart of “Clements” and “Strawberry Plains” plantations to help pay estate debts.  But Isaac fled during the Civil War and made his way to Fortress Monroe, becoming “contraband” -- a second emancipation.   

Shortly afterward, by 1866, Isaac applied for financial assistance from the Freedman’s Bureau to travel home to Nansemond county, bringing his 3 children and a new second wife Ann Gray Holleman.  Within 5 years, 1871, in an extraordinary move, Isaac and Ann bought a 50-acre farm about 2½ miles southeast of Windsor off Tyler Rd (Rt. 608). He paid about $200. Here they reared 10 children who lived. And, as Isaac’s three children with his first wife grew to adulthood, they and their families lived nearby.  The Holleman farm home place was the hub near where Isaac’s children and descendants lived.  Isaac died in 1898. In 1912 the farm ownership changed to son Nonnie J. Holleman. It stayed in the family until the late 1940s. Later, it became part of N&W Railroad property, and is still farmed today by rental from NWRR.  The farm home, other structures, and a small cemetery at the home farm where Isaac is buried are now plowed over. Nonnie, son of Isaac and Ann, is buried with several siblings and descendants in the nearby Tyler cemetery just a mile from the Holleman farm. Also buried there is Georgie Tyler, the Superintendent of schools for black students during segregation. The cemetery is on a farm of her husband Harvey’s family. 

The Windsor Middle school is named for Georgie Davis Tyler. There is a display about her in the school. Mrs. Tyler first began teaching in the one room school called Muddy Fork in 1912, then for two years at Blooming Light Hall, then teaching with Mr. George Gwaltney at the new, two room Windsor School, sometimes called Sugar Hill. After three years she was appointed a Jeanes Supervisor. During that time there were 27 schools, and she was to visit each one twice per month. She retired in 1946.  Named for her in 1950 were an elementary and high school in Windsor. The new middle school that opened in 2014 is now named for her.       

Reference: H. H. King, Historic Isle of Wight County, Virginia, pp 155-158.  See also:  https://www.historicisleofwight.com/uploads/5/4/0/5/5405029/tyler_bio.pdf

http://www.theschoolhousemuseum.org/FormerEducatorsandbrSupportPersonnel/tabid/176/Default.aspx https://www.thetidewaternews.com/2014/09/12/iwcs-comes-full-circle-with-opening-of-new-middle-school/

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