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.

Reflections Concerning Isaac Holleman, Part 3

by Glenn N. Holliman

This continues the saga of Isaac Holleman, born in 1818 into slavery at the Josiah Holleman plantation in Mill Swamp, Isle of Wight County, Virginia.  This time line prepared by Susan G. White, direct descendant of Josiah and major historian of the life and times of Isaac Holleman and his wives.  The words in italics are mine, reflecting on the confusion of the Civil War era.- GNH

A picket fence stands before the current house at Stawberry Plains, the original Urquhart plantation in Isle of Wight County, Virginia.

1848    Josiah Holleman died.  Isaac Holleman sold back into slavery for $355 by executor Isaac Cofer, to Richard A. Urquhart, a wealthy slave owner who lived at Strawberry Plains, about 6 miles from Josiah’s home.

            Malinda Pretlow’s father, Moses Pretlow, is on a list of Josiah Holleman’s debts, in Josiah’s handwriting, of being owed $2.76.  Malinda was the mother of Isaac's first three children.

           Moses and Malinda were free; Isaac was enslaved.  The nuances of Virginia society in the antebellum South are fascinating and puncture the 'Gone with the Wind' concept of a static society.  Free African-Americans lived side by side with enslaved persons and European-Americans, some slave owners, others yeoman farmers working the land with family members or hired hands.  

1850       One black male slave, age 30, Richard Urquhart’s slave schedule (believed to Isaac)

1852       Birth of Isaac’s son Robert Holleman, to mother Malinda Pretlow

1854       Birth of daughter Ada, to mother Malinda Pretlow

1858       Birth of son Moses to mother Malinda Pretlow

1860       Richard Urquhart dead.  His widow continued to own slaves.  Census schedule shows 133 slaves, of whom 2 males are ages 45 and 40.  Isaac would be 42 by then.  He would know the domestic slave quarters still standing on Strawberry Plains Farm.

            Census records reveal that Stawberry Plains was the second largest community of enslaved persons in Isle of Wight County prior to the Civil War.  Enslaved plantations of this magnitude were the exception in American slavery.  One can scarcely imagine the sub-cultures within a population of this size.

                Free Negro Malinda Pretlow is listed on the 1860 census, shown a few dwellings down from R. Pretlow.  She lived on Proctor’s Bridge Road, in Southampton County, west of Proctor’s Bridge.

           During the Civil War, Fortress Monroe located on the north side of the James River, some miles east of Isle of Wight County, became a haven for 'contrabands', former enslaved persons who escaped to the freedom of the Union Army.  One of these persons was Isaac.  There is a mystery here because his three children of Malinda Pretlow, all born free, either went with him or joined him at Fortress Monroe.  At some point in the Civil War, Malinda, who lived long after the war, and Isaac separated.  Isaac must have met Ann Gray during the confusion of this turbulent period and made her his second wife while at Fortress Monroe.

1866       Freedman’s Bureau records show Isaac petitioning for money October 1866 to return home to Nansemond County, along with Ann Gray Holleman, Robert, Ada, and Moses Holleman, to “escape destitution.”  He also petitions for money due his son Robert for work son did for Mrs. Binford, who lived just west of Proctor’s Bridge in Southampton County.

            Nonnie Holliman and Sandi Royal, descendents of Isaac and Ann Gray at the Stawberry Plains farm March 2022 where their ancestor worked and from which he escaped to freedom during the Civil War.                                                               

 1867       Birth of daughter Luzerne.  Mother is Ann (Gray) Holleman

 1870       Malinda Pretlow listed on Southampton County 1870 census.

1871       January 1.  Isaac and Ann buy farm from Nathaniel P. Phillips, made payment of $50.  Farm previously owned by Cary Eley. This farm located a few miles south of Windsor.

1873       November 11.  Isaac pays remainder of farm money, 194.01, to Phillips’ executor, John R. Kilby, and receives deed to the 50-acre farm.

1876       Birth of son Nonnie

1878       Birth of son Jeremiah

1879       Birth of son Joshua

1880       Isaac, Ann, and children on census

Census farm schedule identified Isaac’s farm and its assets

1881       Birth of son Joseph, who died in infancy, about age 1 yr

1883       Birth of son Joshua

1885       Birth of son John Henry, Sr.

1888       Birth of daughter Joanna

1889       Dec. 23 document of Isaac and Ann paying $50 to trustee George T. Atkins, presumably for a debt to neighbor Richard F. Eley.  Debt was satisfied.

1890       U. S.  census burned.  No records.

1897       Last time Isaac paid taxes on farm.

1898       Farm then in name of “Holleman, Isaac, estate”.

1900       Wife Ann on census, with children living with her.  She owned her own home/farm. The date of her death is unknown.  Both Isaac and Ann are buried on the farm, now in unmarked graves.  The property has been part of the Norfolk Southern Railroad since the 1950s.

So here we have the incrediable, tragic, heroic story of Isaac Holleman who born a slave, freed, taken back into bondage, escaped to freedom, became a land owner during Reconstruction, raised children from two wives and whose descendents today are scattered across the USA.   

Abraham Lincoln in his Gettysburg Address spoke of a 'new birth of freedom' in America.  Isaac perservered in conditions and circumstances unimaginable today.  He bears the name Holleman.  And all, descendants and those of the same surname, salute him for his courage and steadfastness in adversity.  - GNH

Reflections Concerning Isaac Holleman, Part 2

 by Glenn N. Holliman

This reflection continues our exploration into the life and times of Isaac and Ann Gray Holleman, a biracial couple who challenged the strict norms and laws of post Civil War Virginia.  In my previous article I acknowledged and do so again the serious research by Susan G. White, a descendant of Josiah Holleman (1771-1848), who has discovered new facts about this amazing story.  

Susan has prepared a valuable timeline of the events in the life of Isaac.  With this information, I have integrated photographs from a visit of Isaac descendants and several of us in the lineage of Christopher Hollyman (1618-1691), the ancestor of most Hollimans (various spellings) in the United States.  

The parents of Isaac are not known.  At least one Federal census records him as of a mixed race.  Was his mother an African American held in bondage and his father, a man, perhaps a slave owner?  DNA tests have not yet provided us that information.  As early as the 1680s, Virginia law forbade sexual relations between those enslaved and White persons.  As historical and DNA records show, numerous White males through the generations ignored this restriction.

Timeline for Isaac Henry Holleman (1818-1897 ca) by Susan G. White, Hollyman Family Historian

1810       Josiah Holleman owned 9 enslaved people

1811       He bought 2 more, woman Harty and girl Lavinia

1818      Birthdate of Isaac Henry Holleman, according to Freedman’s Bureau record

1820       Josiah Holleman owned 15 enslaved persons, including 9 males

Isaac was born on the original property purchased by Christopher Hollyman in 1684, land that remains in the Holleman family to this day.  The current owner, Billy Joe Holleman, opened wide this ancestral property to a large gathering of Hollemans in 2016 and again he graciously welcomed our group in March 2022.  Josiah Holleman was a 4th great grandson of Christopher's.  One of Josiah's sons, Joel, served as a U.S. Congressman.

Left to right, Tammy Hunt, Susan White, Billy Joe Holleman and Isle of Wight historian, Jim Henderson, on the Holleman farm near the Mill Swamp Baptist Church in IOW county.  This stop one of several on March 12, 2022.  

 

1823      Malinda Pretlow born, Free Person of Color, daughter of Free Black parents             

1830      Josiah owned 14 enslaved persons, including 8 males, 3 ages 10-23

The Holleman House constructed in the 1830s by Josiah Holleman on original land of Christopher Hollyman (1618-1691). It is not unrealistic to imagine young Isaac Holleman had a hand in constructing this federal period structure.     

 1836       Isaac, age 18, emancipated, via Josiah’s petition to the court.  

1840       Josiah’s census listing shows 1 male Free Person of Color, age 10-23, 1 female Free Person of Color under 10, and 8 enslaved beings.   

1848      Josiah died with many debts.  Isaac sold back into slavery for $355 by executor Isaac Cofer, to    Richard A. Urquhart, a very wealthy plantation owner who lived at Strawberry Plains,  8 miles from Josiah’s home.  Malinda’s father, Moses Pretlow, is on list of Josiah   Holleman’s  debts, in Josiah’s handwriting, of being owed $2.76. 

            Fear and Stress in Pre-Civil War Society

            A decade before Josiah's death, the 1831 Nat Turner slave rebellion occurred in nearby Southampton County resulting in the death of any many as 55 persons.  This incident terrorized the White south as it fulfilled the greatest fear of slave owners!  Night patrols of anxious local authorities road at night insured no enslaved persons stirred from their homes without permission.

            A generation prior to the Civil War, the tobacco economy of Virginia suffered as the soil worked in earlier generations was exhausted of nutrients.  Josiah's indebtedness at death is a vivid example of the increasing economic challenges of Virginia enslavement plantations to be profitable.  Nearby Richmond had become a slave trading mecca where tens of thousands of human beings were sold at auction.  

            In many. many cases persons were separated from their families and homes and literally in chains marched hundreds of miles to the newer, soil rich plantations in Alabama and Mississippi. This nefarious system shattered the unity of African-America families, their security and fragile culture.  The ramifications of this evil institution ricochet through American society to this day.        

          Questions and Thoughts to be Considered

                                                   Nonnie Holliman and Sandi Royal

            On our way back to Richmond, Susan White, Sandi Royal, Nonnie Holliman and I speculated  on several issues in this story.  As I wrote years ago (click on name of Isaac Holleman in left column), pre-Civil War IOW of Wight County was an uneasy, largely agrarian, society of slave plantations, yeoman White farmers with no persons held in bondage and numerous Free Persons of Color. 

         1. Why, when Isaac received emancipation in 1836, he was again enslaved by 1848 and sold to pay Josiah's estate debts?  Had Isaac, who as a Free Person of Color with very limited civil rights after legal emancipation, violated a law, a slave code of the time, and as punishment forced back into to bondage?  There are cases of this happening.

            2. We noted Josiah owed money at his death to Moses Pretlow, a free person and father of Malinda, Isaac's first wife.  There then was some integrity in a system that recognized contract law even with free African-Americans who navigated a precarious legal and societal existence.

            3. Moses was the father of Malinda Pretlow, who 'jumped the broomstick' with Isaac and bore him at least three children, perhaps two others.  'Jumping the brook stick' literally was the folk custom of marriage of enslave persons prior to establishing legal rights after the Civil War.   

            Left to right at the Pretlow farm near where Malinda Pretlow lived are Doris Knox and Tammy Hunt, direct descendants from Isaac and his first wife Malinda.  Far right is Nonnie Holliman, descended from Isaac and Ann Gray Holleman.  The empty house in the background was constructed ca 1870 during the Reconstruction Period.

               Malinda lived approximately a mile (as the crow flies) from the Holleman plantation eventually living separately from her father.   This couple had three children before the Civil War which evidently led to their separation. 

At the Pretlow farm, current owners Mary Leatherwood and Adrian West shared an aerial photograph of the property as it looked in the early 20th Century

How did the couple sustain a relationship that resulted in children, separated as they were by some distance and legal status?  At age 30, Isaac had to move to Strawberry Plains, a farming community of over 100 enslaved African-Americans, miles away from Malinda.  Perhaps this doomed the marriage?

Next article more information and yet more questions on this story of 19th Century America, an America that had yet to live into its creed of liberty and justice for all. Only a Civil war would give Isaac and millions of others 'a new birth of freedom.'-GNH

 

Reflections concerning Isaac Holleman, 1818-1898 ca

 by Glenn N. Holliman

Daffodils tell a Story

On March 12, 2022, a Holleman/Holliman family group, all descended from ancestors of Isle of Wight County, Virginia, finished a late lunch in Windsor, Virginia. It had rained 'cats and dogs' that morning but after the sky had emptied several inches of rain, a nasty, windy cold front moved in, and later a wet snow fell.  We were a three, sometimes a four, car convoy visiting Holleman ancestry sites, on a blustery day in late winter.

Above, at an earlier stop before lunch near Windsor.  Susan White, our leader, shivering in blue, Tammy Hunt, Sandi Royal, Kimberly Holliman and her father Paul Holliman listening to a lecture at a century old country store by Jim Henderson (not visible) of the IOW Historical Society.  

Refreshed by a quick meal, our convoy headed east on Old Suffolk Road. The rain eased, although not the wind chill.  We turned south on Tyler Road, drove a half mile or so, stopped at the Tyler Cemetery.  

Here we visited the resting places of the African-American Hollemans, often spelled Holliman, many descendants of Isaac Holleman.  

Isaac Holleman was our reason for this trip.  He had been born a slave into the household of Josiah Holleman of Mill Swamp, IOW, in 1818.  His story has intrigued me since I heard it in 2012 from Sandi Royal, a descendant of Isaac.

Isaac's great grandson, Nonnie Holliman, pictured here visiting his grandfather's resting place, was in our group, as well as others who descended from Isaac.  Nonnie, retired from Federal service,  drove all the way from his home in Syracuse, New York to make this pilgrimage to the town in which he grew up.  

The genealogist who had arranged the trip, Susan White, of Richmond, descendent of Josiah, has gathered in the past year a monumental amount of research on Isaac and his two wives, Malinda Pretlow and Ann Gray. 

Susan has written the past three blogs on Isaac and his incredible story.  She is an often visitor to the Library of Virginia, the Virginia Baptist Historical Society Library, and the archives of IOW county.  Those of us studying the Hollyman families in Virginia owe her a great debt of gratitude.

Utilizing her research and that of historian Jim Henderson of IOW Historical Society who also accompanied us, I add my own reflections and tip my hat to both of them.

At the Tyler Cemetery, Kimberly Holliman, Sandi Royal, this writer, Tammy Hunt and Doris Knox

The water table in this part of southeast Virginia is close to the surface hence the concrete tablets to secure the grave sites.  

Isaac escaped bondage during to the Civil War and found sanctuary at Fortress Monroe, a Union outpost. There he must have met and married the mysterious Ann Gray.  Destitute after the war and with children from his first wife, Malinda, and now children with Ann, somehow he was able to purchase a 50 acre farm in 1871.  Susan believes he died there before 1899 and his wife, a few years later.  In her research Susan discovered the location of the farm near Tyler Cemetery.

Are this biracial couple buried in Tyler Cemetery?  No, that is not their resting place.  Nonnie, who had spent time on the farm in childhood (it stayed in the Holleman family until 1954), believes the couple is buried on their farm.  

We boarded our automobiles, studied our maps and headed further south along Tyler Road, past the turn off at Dunston Road, and drove a bit further.  The farm had been purchased by the railroad and now the land along Tyler was now brush, trees and shrub.  We could find no entrance into where we knew from the map that the farm had been located.

And then we spotted the daffodils.

 

Daffodils are not native to North America.  They have to be planted.  According to author Kelly Gamey, who photographs and writes of forsaken southern properties, a clump of isolated daffodils in the spring are 'ghost gardens', bulbs buried in previous decades by former inhabitants of abandoned sites.  You might check out her site at kelly@theforgottensouth.com.

There were no other daffodils along the road.  This had to be the lost entrance to the Isaac and Ann Gray farm.  Somewhere in the bush probably lay the foundations of a home and graves.  But we were not equipped for an exploratory hike in the marshy woodlands that cold afternoon. 

We stopped, took photos, and chilled as we were, called it a day.  I rode with Susan, our driver and historian, and Sandi and Nonnie, all of us returning to Richmond.  We said goodbye to Tammy and Doris of Southampton County.  And also Paul, Teresa and Kimberly Holliman, residents of Williamsburg and alumni of our 2019 Hollyman excursion to England.  They ferried across the James River, coming and going to be with us that day.

On the way back it snowed several inches and the temperature kept dropping.  But our hearts were warmed by what we had seen and heard that day.

And more on the trip in the next blog as we explore further the life and times of Isaac Holleman.....

The Saga of Isaac and Ann Gray Holleman, Part 3

 

The story of the biracial couple of 19th Century Isle of Wight, Virginia continues, written by Susan G. White (pictured right), a family historian known for her research and careful conclusions. We are grateful to her for sharing her insights and gathering information thoughtfully from the ancestors of this courageous couple. - Glenn N. Holliman

Enter Ann Gray, a White woman. Ann has been the subject of much speculation and interest in current-day Holleman researchers.  For generations, Black Hollemans have told of Isaac and Ann’s complicated relationship in their oral history, that Isaac and Ann fled from her angry family in their initial love.  

White Holleman researchers have tried to connect Ann with Gray ancestors who were closely connected with Josiah Holleman, or to other Ann Grays in Isle of Wight, but to no avail.   Sandi Royal, a descendent of Isaac’s son Joshua, Denise Keeter Goff, an excellent Holleman researcher, and I worked hard this past summer of 2021 to track down Ann’s parents.  

Sandi finally summed it up perfectly, “We will probably never know who Ann’s parents were.”  Be that as it may, somehow, Isaac and Ann met and found a life together.

Above, Glenn N. Holliman and Sandi Royal discussing the Isaac and Ann Gray Holleman story in 2012 in Chester, Virginia.

We know of Isaac and Ann’s life first by way of Freedman’s Bureau records.  Isaac petitioned the Freedman’s Bureau in October 1865, from Fort Monroe, Virginia, to request money for him, Ann, and his three children Robert, Ada, and Moses, to return to Nansemond county, Virginia, to “escape destitution.”  

He also requested help from the Bureau that his son Robert Holleman be reimbursed for the money owed to him for working for the “Widow Binford.”  Mrs. Binford and her husband lived one dwelling away from Malinda Pretlow in the 1860 Southampton County census.  Isaac was working to get what he felt he was due after the war, in order to survive.  

We can wonder how it was that Isaac, Ann, and the 3 children ended up at Ft. Monroe?  The fort was under Union control during the Civil War, and commanded by General Benjamin Butler.  

The general famously would not return slaves who had fled to Ft. Monroe to Confederate owners; he called the slaves “contraband of war.”  Large numbers of slaves found the destination of Ft. Monroe to be sanctuary, and we can guess that Isaac and family were no different. 

In her famous book on the history of Isle of Wight County, Helen Harverty King wrote the following:

'The county was in desperate circumstances by the end of 1863. The season had been bad, almost the entire slave population was gone, the call came for more recruits for the army, the insecurity of persons and property was made greater by frequent enemy visits and there was a great scarcity of necessities for life on the home front."

 Isaac’s three children with his first wife Malinda Pretlow were Robert, Ada, and Moses, all who have been well documented.  Robert married Cassandra Daughtry, and had 10 children; he stayed in the Isle of Wight area.  Ada  married Jacob Ely, and after she died, Jacob married her half-sister Lucerne Holleman, a daughter of Isaac and Ann.  Moses married first Eugenia Randal/Randolph, and after she died, he married her sister, Ann Eliza Randal/Randolph.

Above on an excursion in Isle of Wight County, Virginia in 2012 are left to right: Tammy Hunt, Cyndi Barnett, Doris Knox, Robert Royal and in the background, Sandi Royal. Tammy is a descendant of Isaac and Malinda; Cyndi, Doris and Sandi all are descendants of Isaac and Ann Gray Holleman. Robert is Sandi’s husband.  They are all standing on Proctor’s Bridge overlooking the Blackwater River, not far from the ancestral farms of the Binfords, Pretlows and Hollemans.

Census records have been fruitful in uncovering Isaac’s story, with one exception.  We cannot find Isaac and family anywhere in the 1870 census that would explain where they moved to after Ft. Monroe.  

Why did they request transportation to Nansemond county, southeast of Isle of Wight, instead of back to Isle of Wight?  

All comes well, though, in the 1880 census and farm schedule, where Isaac, Ann, and family owned a 50-acre farm in the Windsor district of Isle of Wight.  They had a total of 10 children:  Luzerne, Roxanna, or Roxie, Addie Lou, Nonnie James, Isaac Thomas, Sr., Jeremiah, Joseph, Joshua Sr., John H. Sr., and Joanna. 

Recent examination of Isle of Wight land tax records revealed that Isaac paid tax on his farm located 9 miles south of the county courthouse until 1897, and we know that he fathered daughter Joanna, also in 1897.  His land entry was entitled “Holleman, Isaac, estate” in 1898, so we can safely assume he died in 1897 or 1898.  Ann shows on the 1900 census as a farmer, owning her home, and widowed.   Further land tax records continue to refer to the farm as Isaac’s estate.

This story of Isaac Holleman and his remarkable life in Isle of Wight county, Virginia, shows resilience, persistence, and honor in achieving his freedom in ways we find difficult to fathom.  

He survived slavery twice, gained emancipation, survived the Civil War, Reconstruction, and Jim Crow.  Isaac’s proximity to Fort Monroe, Virginia and Isle of Wight, Virginia illustrate the geographical, political, and historical connections of slavery in our Holleman family.

Isaac’s children’s stories continue, with descendants Black and White uncovering and sharing them.  Perhaps we can share them later. -Susan G. White 

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