Honoring Sacrifices, Dreams you nurtured, and the Love you bestowed upon our Lineage.

Honoring Those Who Came Before Us, Isaac and Ann Grey Holleman

by Susan White, Holleman Genealogists and Historian

Editor's note, this is the climax of the Isaac and Ann Grey Holleman story which first surfaced in this blog when your editor shared lunch with Sandi Royal in 2013.  Descendants of  Josiah Holleman of Isle of Wight County, Virgina, both African-American and European American, have been jointly researching this American story for over a decade.  On Saturday, March 1, 2025, Isaac Holleman descendants visited the site of Isaac's farm, one mile south of the town of Windsor, Virginia, off Route 608. Susan White explains how the story unfolded. - Glenn N. Holliman

 Family

Our white Holleman ancestors in Isle of Wight, Virginia, enslaved people.  We don’t know if that practice started with Christopher Holleman (Holliman, Hollyman), our first immigrant, but it could have.  Christopher grew tobacco, a labor- intensive crop, and must have needed helpers for his harvest.  My fifth great grandfather, Josiah Holleman, (1771-1848) enslaved at least eleven Black men, women, and children during his lifetime, including Isaac Holleman (1818-abt 1898), the main subject of my family genealogical research for years.  He fathered Isaac, and at least one other Black man, James (1825-unk) with an enslaved Black woman. Isaac’s story was shared in public at a presentation sponsored by the Isle of Wight Historical Society on June 22, 2024 at the Georgie Tyler Middle School, Windsor, Virginia. 

Isaac’s descendants, have been enlarging this story that continues to broaden.  Glenn Holliman first mentioned Isaac in his 27 June 2013 blog post where he spoke of Sandi Royal’s research and retelling of family lore, that Isaac “ran off with Ann Gray, a white woman,” whose family was against the relationship.  Sandi spoke of a picture of a “white woman” that hung in her family’s house for years.  I learned of this story in 2016, from Glenn, at a Smithfield, Virginia Holleman family reunion.

 Glenn N. Holliman and Susan White at a 2016 Isle of Wight conference. 

At that time, I had just begun to research my own connection with Josiah Holleman, who was my fifth great grandfather.  One of his sons, William Henry Holleman (1795-1834), was my own Holleman ancestor, and he was an enslaver, as well.  Identifying the relationships between my Holleman enslavers and enslaved people around Isle of Wight county in the eighteenth and nineteenth centuries has been and continues to be difficult. We discovered some of the truth of Ann Gray, however, and where she came from, most likely Nansemond County, VA.  Sandi Royal, my daughter Lea Marshall, my brother, Eddie Gallier and I have used the tools of DNA, paper records, National Archives aerial photography, and sometimes pure dumb luck to dig into this story.                

Isaac fathered children first with Malinda Pretlow, a free Black woman, and then with his wife, Ann Gray.  Descendants from both unions have connected over the past few years to learn more about their roots.

Sandra Royal 

 

                                                               Nonnie L. Holliman
                   

 Kenya Allmond

 

The Family Farm in Windsor                       

 After their escape from enslavement during the Civil War, Isaac and Ann Holleman bought a 50 acre farm in 1871, about a mile south of the town of Windsor, Virginia.  This was no small feat.  They owned their farm, did not sharecrop, and the farm stayed in the family until 1963, when  James Trueheart Holliman, a grandson of Isaac, sold the farm to W. T. Joyner.  It was sold one more time before the Norfolk and Western Railroad bought it in the early 1990’s.   

The 1880 agricultural schedule reveals his livestock and crops and the effort Isaac was expending to provide for his family:

1 horse, 1 mule, 1 working ox, 1milch cow and calf, 9 swine and 13 poultry

100 bushels of corn, 20 bushels of sweet potatoes, 50 bushels of apples, 50 bushels of peaches.

He cut 60 cords of wood the year previous.

About 2023, in one of those lovely serendipities of genealogical research, Jim Henderson of the Isle of Wight County Historical Society discovered an old file on his computer that another Society member must have shared with him at some point along the way. The file was a part of an environmental impact study undertaken by William and Mary Archaeological Department for the Norfolk and Western railroad (now Norfolk Southern Railway) as it was buying the farm from the Joyner family.  Another stroke of good fortune was that the archaeologists met Reverend Arthur Holleman, a great-grandson of Isaac, who knew the farm when it was in the family, and enlisted his help to identify what they were finding in their labors. 

 To read the report is to marvel at what Isaac Holleman accomplished.  Unfortunately, as time passed, the farm became lost to the descendants who lived in the area.  No one living knew exactly where it was.  On two different occasions, a group of Hollemans attempted to find it using the maps in the Norfolk and Western study, but we were not very good at reading the many-times-copied maps.  The third try was successful, and luck was with us again. 

In November, 2023, as the county farmers were harvesting their cotton crops, we discovered the dirt road off of Route 608 in Isle of Wight, and the chain across it was down.  We were able to drive down the rutted road and found the farm.  About 8 bales of cotton were stored at the edge of the field, waiting to be taken to the cotton gin.  Jim and I got out of the car and began to walk the field of cotton stubble.  It was a beautiful day and we were very excited.  Jim wondered who farmed the field?  Maybe we could find out?  

It was late in the day, but Jim thought we should drive over to the cotton gin facility, to see what we could find out.  Luck prevailed again.  The owner of the gin gave us a name of possible farmer, and I called him.  He was not the one in this case, but he gave us the name of who he thought might be our man, and Success!  Mike Griffin was the farmer who still leases this land from Norfolk Southern Railway.  He has been farming the field since about 1995.  

                                                     Susan White and Lea Marshall

In January, 2024, my daughter Lea and her husband, Will Kerner, visited the farm, this time hoping to obtain more pictures.  Will has a drone camera, and he was able that day to take aerial pictures.  It was a cold, dreary day, and this time the chain at the entrance to the dirt road was in place and locked.  We had to walk the long, muddy road to come to the field, rather than driving.

Courtesy of William Kerner, this photograph shows a dirt road separating the field of standing water (left) from the green field in the upper center of the photograph.  Windsor is the white border upper right. 

Jim Henderson has encouraged us consistently for several years in uncovering Isaac Holleman’s story.  In 2024, he invited us to present what we were learning to the Isle of Wight Historical Society.  Our group, in particular, Sandi Royal and Nonnie Holliman, who are both Isaac descendants, agreed.  My daughter, Lea, my brother, Eddie Gallier, and Glenn Holliman were also eager to share the story.   

                                                                                                             

 Eddie Gallier (pictured) is an avid modeler, particularly in constructing model train layouts.  The man has skills.  I asked if he would help us to create a model of Isaac’s farm.  He agreed, and in 2023, in order to learn more about the farm, he contacted the U. S.  National Archives to inquire about U. S. Department of Agriculture aerial mapping.  Thanks to the generosity of several family members, Eddie obtained the 1930’s-1950’s aerial photos of the Holleman farm from the Archives. 

1938 aerial view of farm with structures in the middle of the picture.

He also had the N and W study in which to refer. Eddie then created the farm layout in a HO model railroad gauge showing the house, barn, outbuildings, well, smokehouse, the family graveyard and the orchard.  He photographed them all, so they could be included in our presentation.

                                                        Model of farm by Eddie Gallier

 On June 22, 2024, as part of Isle of Wight Historical Society’s Juneteenth observation, we told “The Extraordinary Life of Isaac H. Holleman” at Georgie Tyler Middle School.  About eighty people attended, many of them descendants of Isaac, Malinda, and Ann. 

Season and Weather

Our research group has visited various Holleman related sites in Isle of Wight over the past 3 to 4 years.  One day was in March, bitter cold and snowy. Then a couple of summer days where I got chigger bites in the Tyler Cemetery. Then another beautiful late fall day, and a dreary, depressing January day.  Doing so, however, revealed another layer in Isaac’s life.  He had encountered all kinds of these days during his life in Isle of Wight.  We were fortunate to encounter them, also.

Now we know where the farm is and can visit, but because the Holleman farm is an actively cultivated field, we visit with full knowledge of season and weather and respect the farmer's work. We can visit from early December until mid-March.  We have trudged through mud and crop stubble, as Isaac and his family did.  This spring we rescheduled twice a trip due to snow. 

This past March we finally made it on a warm, early spring day, occasionally windy, but not uncomfortable.  As we crossed the swampy area at the entrance of the field, we heard frogs.  We heard the headwaters of Ely Swamp gurgle.  You could hear the wind.  Below muddy fields and swampy bogs.                                                 

Prior to our trip, my brother had helped me load coordinates into my phone Google map, of the family graveyard, the  house, barn, and the orchard.                               

 

 We made our way across the field, hammered stakes into those sites. We stopped at the graveyard site and prayed a prayer that Nonnie Holliman had written for us.

 

Right to left: Nashawn Holliman, Alexander Holliman, Kenya Allmond, friend of Kenya, Sandi Royal

A Prayer of Remembrance for Ancestors at the Holliman Farm, March 2025

Dear God and Ancestors,

We gather in reverence and gratitude, remembering your spirit, your wisdom, and your strength. Your journey through life laid the foundation upon which we stand, and your legacy continues to guide us with every step we take. We honor your sacrifices, the dreams you nurtured, and the love you bestowed upon our lineage. Your stories, though sometimes untold, are woven into the fabric of our existence, and we cherish the lessons they impart. May we always strive to live in a way that makes you proud, carrying forward your virtues and values. As we reflect on your lives, we seek your guidance and protection. Help us to face our challenges with the same courage you displayed, and to celebrate our triumphs with the same joy you felt. May we be ever mindful of the paths you forged, and may our actions today honor your memory. In moments of doubt, may we feel your presence, and in times of celebration, may we sense your joy. Your spirits dwell within us, a constant reminder of the enduring bond we share. We are eternally grateful for the roots you have planted and the legacy you have left behind.

With deep respect and love, we remember you. Amen.

By Reverend/Superintendent Nonnie L. Holliman, Great Grandson of Isaac and Ann

 That day we could be where Isaac and his family lived and died.  It was a very good day.

The Saga of Isaac and Ann Gray Holleman, Part 2

 

Susan White, major Hollyman family researcher, continues the amazing story of the biracial couple, Isaac Holleman, enslaved to Josiah Holleman, and Ann Gray, a White girl, who became Isaac's second wife during the American Civil War. - Glenn N. Holliman

We know from the date of Isaac Holleman’s emancipation in 1836 that he was born in 1818.  He was likely one of the 4 black male slaves under 14 on the 1820 census listing for Josiah Holleman, plantation owner of the original Hollyman land dating from 1684.  Isaac continued to live on Josiah’s land, showing up on the 1830 census as one of 3 black male slaves age 10-23.  He would have been 12.  

Josiah petitioned the Isle of Wight Court on April 4, 1836, for Isaac’s freedom, and it was granted.  We do not know why Josiah chose to free him and can only speculate.  This fact is even more confounding on the 1840 census, where Josiah’s listing of slaves shows a free black male age 10-23 who would be Isaac, age 22, and a free black female, under age 10.  Six slaves of Josiah’s are also listed on this census, 3 males and 3 females.

Above, the Holleman House in Isle of Wight County, Virginia.  The house still sits on farmland in the Mill Swamp district purchased by English immigrant Christopher Hollyman (1618-1691). This home was built in the 1830s.  This picture is from 1907, forty-two years after the 13th Amendment to the Constitution freeing the slaves.  Isaac would have known this home and most probably helped construct it.

Josiah wrote his will in 1847, leaving named slaves, including Isaac, to his executor, Isaac Cofer.  No mention is made of Isaac’s emancipation in the will.  

Unfortunately, Josiah’s estate did not contain enough money to satisfy its debt, and sale of Isaac is listed in the estate auction to raise funds. Isaac’s sale added $355 to Josiah Holleman’s estate. Research indicates Josiah (1771-1848) had been suffering from what we now call dementia and that could have contributed to his inadequate financial situation.

Isaaq was bought by nearby neighbor Richard Urquehart. a particularly wealthy man in the county, living on his plantation, Strawberry Plains, with 88 slaves listed on his 1850 census. 

This 1864 map is not easy to read.  It is of Isle of Wight County, Virginia with the borders of Surrey County in the top left and Southampton County, lower right.  The Holleman plantation is center top, diagramed in color with the words 'Mill Swamp' just to the right.  The Richard Urquhart home is south of the Holleman home, and is named for “Widow Urquhart.”   If one looks closely one will see three farms owned by Grays.  Susan and Denise Keeter Goff’s research is that Ann Gray did not belong to one of these families.

Richard died in 1857, and his widow Mary continued to manage the plantation.  “Widow Urquehart,” as she is referred to on the 1864 map of the county, owned 113 slaves on the 1860 census, an amazing number indicating immense wealth.  Three Black males, age 40, are listed on the 1860 slave schedule for her.  One of these is most likely Isaac; he would have been 42 in that year.

Josiah Holleman’s land was in the northwest corner of Isle of Wight County, near where Surry and Southampton counties meet with Isle of Wight.  Free Negroes lived in these counties, and one Moses Pretlow, lived in Surry County, just north over the Surry/Isle of Wight line, not far from Josiah’s land.

Moses apprenticed to Henry Callcote in 1833, and married Rhoda by 1820, as shown on the census.  They raised a family of 7 children, Malinda, Riley, Ann, Mary, John, Michael, and Major.   Moses continued a Free Black, appearing with his family, also free, on census listings from 1820-1850.  Moses farmed his own land in Surry County.   

Moses’ story is important to Isaac’s story because not only he, but also his children were free.  We would have had much difficulty tracing Moses had he been enslaved.  His oldest daughter, Malinda, appears in Isaac’s story beginning in the 1860 census, with 5 other people, Virginia Pretlow, 22, Robert, 11, Ada, 8, Moses, 6, and baby Isaac, age 2 months, all with surname Pretlow.  We don’t know who Virginia is, but based on Freedman’s Records of 1865, Isaac had 3 children then, Robert, 15, Ada, 11, and Moses, 7.  Baby Isaac remains a mystery.  Malinda and her family moved from Surry County to the east side of the Nottoway River, in Southampton County by 1860. 

Interestingly, a White Pretlow family, Robert and Roanna Pretlow, with son Charles, lived along the same road as she, 3 households apart, and the family in between was Moses’ widow, Rhoda, with her still at-home children.  The white Pretlow family pops up again in later years.  The last known location of Malinda is in the 1870 census, listed with surname Holleman. She was Isaac Holleman’s first wife, and continued to live in Southampton County.  A young woman Levinia lived with her, along with 3 black males, Dawson, Hilliard, and Thomas Holleman.  Their relationship to Malinda is unknown.

The Pretlow House from a Historical Structural Survey of Southampton County, Virginia with commentary below.

A house built by Charles Pretlow, was described in a 2008 survey of Southampton County homes, and we include it here to illustrate the neighborhood our characters knew.  “The Charles Pretlow Farmhouse at 37165 Pretlow Drive, is a good example of the vernacular Victorian styles. A frame, two-story, five-bay, central hallway building with interior gable-end chimneys; the house is one-room deep and has a rear one-story kitchen ell. This dwelling has a shallow gable roof with a box cornice with partial returns and decorative brackets. The front entrance porch is supported by paired square wood posts with a cutout star decoration on each side, filigree trim, and scroll brackets. The style (of the Charles Pretlow House) most often observed in Southampton County is vernacular Victorian (referred to as “folk”). Adapted into existing traditional building styles such as the I-house (two-story, one-room deep, central hallway) plan, one or two-story gable-front with side-wing (L-shaped) dwellings, pyramidal hipped with recessed porch, plus front or side-gabled structures, vernacular Victorian was common during the period from about 1870 until about 1910. 

 The Victorian features added to these folk buildings are usually Italianate or Queen Anne inspired decoration, which are typically less elaborate than the high style Victorian interpretations. Typical features might be a full return cornice with brackets under the eaves and/or spindle work porch detailing.”

In a third article, the saga of Isaac and Ann Gray Holleman will continue.  Information on the Holleman House and its history can be found in earlier blogs.  An archive of Hollyman (many spellings) and associated families can be found at www.bholliman.com.

The American Hollyman families are featured also in Hollyman Family at Ancestry.com managed by Jeanette Holiman Stewart who has information on over 70,000 family members!

Tina Peddie, long time Hollyman genealogist, maintains the Hollyman Family Facebook page. - GNH