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 of Isle of Wight, Part 1

by Susan Gallier White

Susan G. White of Virginia is one of the more scholarly writers of  Holleman/Holliman family history of our generation. What follows is the first article of several of the latest information into the fascinating story of an unlikely 19th Century couple, Isaac and Ann Gray Holleman of Isle of Wight County, Virginia. 

In her research, Susan had consultations with Nonnie Holliman and Sandi Royal, who descend from Isaac and Ann, and Troy Jenkins who descends from Isaac's first wife, Malinda Pretlow.  At this site, earlier articles on Isaac and Ann Holleman were published in September 2012 and May/June 2013 by yours truly.  Mrs. White's work greatly enlarges our knowledge of this American story.

Susan wrote August 2016 at this site of her ‘ahead of their time’ Holleman and Faison ancestral grandmothers.  Susan also attended the Spring 2016 Holliman/Holleman in Isle of Wight and later the Spring 2019 Hollyman ancestral exploration in England. - Glenn N. Holliman

 

Above, Susan and I converse at our opening session of the May 2019 Hollyman gathering in Moreton in Marsh, England.  Back right is cousin Lindsay Holliman, descended as were all Hollimans present, from 15th Century Cuddington, Buckinghamshire, England.  Lindsay lives in Edenborough, Scotland.

Isaac Holleman, a Black man, owned by Josiah Holleman, was born into slavery in 1818 at Mill Swamp district, Isle of Wight County, Virginia.  Emancipated in 1836, he was enslaved again in 1848 to Richard Urquehart, to help pay Josiah Holleman’s estate debts. 

During the Civil War, he fled with his family, including his White wife Ann Gray to Fortress Monroe, Virginia when it was commanded by Union General Benjamin Butler.  Butler, a career Massachusetts politician, regarded Black runaway slaves as contraband, and refused to return them to their owners.  Contrabands by the tens of thousands experienced freedom wherever Union Armies marched.  

One such family was named Holleman.

The 1830s Holleman house is on the original land purchased in 1684 at Mill Swamp, Isle of Wight County, Virginia by Christopher Hollyman, (1618-1691) founder of most of the Hollimans (various spellings) in the United States. This picture taken in 2016 as Hollemans/Hollimans/etc. gathered from all over the country.  The home is owned by Billy Joe Holleman.

After the war, Isaac requested and was granted transportation for himself and his family to Nansemond County, Virginia, in October 1865. He settled in Isle of Wight County, bought a farm of 35 acres, where he lived with his second wife, Ann Gray.  Isaac’s date of death is unknown. His story is only recently discovered by White Holleman descendants but has been in the oral history of his Black family handed down by generations.

 Freed persons with Union Soldiers at Fortress Monroe during the Civil War.

The distance between Mill Swamp Road, Isle of Wight, Virginia, and Fortress Monroe, Virginia is about 36 miles.  The elapse of time between 1619, when slaves were first brought to Jamestown, Virginia and 1818, when slave Isaac Holleman was born, is almost 200 years.

Holleman ancestors were part of that distance and time span beginning in May 1650, when Christopher Hollyman came to Isle of Wight County, Virginia from Bedfordshire, England.  

Thirty-four years later, at age 66, Christopher patented 1020 acres of land in the Mill Swamp area.  The son of an inn keeper and shoemaker, Mr. Holleman undoubtedly succeeded beyond his wildest dreams.  He died at age 73 and divided his plantation which bordered Surrey County among his four sons. Tobacco barns were recorded in his will but no slaves. 

The slave economy grew slowly in the 1600s, but exports of Africans in bondage exploded in 18^th Century Virginia.  It was in the 1700s when most likely the ancestors of Isaac arrived in Virginia.  This tragic plantation economy ironically supported many founders of the new United States – for example, Patrick Henry, Thomas Jefferson, George Washington, James Madison and James Monroe.

Fortress Monroe, Hampton Roads, Virginia in the 19th Century where Confederate President Jefferson Davis was imprisoned in chains after the Civil War.  The Isaac Hollemans at the same fort experienced the opposite – freedom!

Four generations after Christopher’s death, one of his second great grandsons, Josiah Holleman, lived on the patented land, in the northwest corner of Isle of Wight, near Mill Swamp.  

Reflecting the growth of human bondage as a norm, Josiah owned 9 slaves on the 1810 Isle of Wight census; no other information listed.  One year later, he bought Negro woman Harty and Negro girl Levinia in a complicated 3-way transaction.

For decades, the plantation economy built on slavery at Mill Swamp prospered, but eventually farming practices at the time depleted Virginia soil and led to economic destress such as experienced when Josiah Holleman died in debt in 1840s.  This situation would affect the future of Isaac. - Susan G. White

Part II of the Saga of Isaac and Ann Gray Holleman by Susan G. White follows in our next blog.