Pineland – 1600 Robertson Road, Wylliesburg, Charlotte Co., VA.


1600 Robertson Road

Wylliesburg VA 23976

N36.501556 W-78.335437

Pineland was a 2,000 acre plantation owned by Charles Henry and his first wife Peggy Osborne Robertson.  Charles and Peggy married in 1828 and the home was finished in 1835.  It had eight rooms, a cellar with two rooms one being a wine cellar.  The parlor was on the first floor and the bedrooms were on the second floor.

Some of the crops grown were Indian corn, Irish and sweet potatoes, honey, wax, wheat and hay.  Livestock consisted of cows, mules, horses. oxen, sheep and swine.  Samuel E. Spaulding was overseer.

The home remained unharmed during the Civil War but they were hit hard financially.  Charles was married by then to Dora Lyman Judd and needed to secure a future for his wife and their children.  He set up trusteeships in 1866 but in 1871 these deeds were overturned by creditors so Pineland went up for auction.  Samuel E. Spaulding placed the highest bid.  Dora used her own money to buy a part of the house tract.  She made the deed out to Mr. Spaulding.  Charles passed away in 1880 and their two youngest sons farmed the land until 1883 when Samuel E. Spaulding lost it to John Booker for debts.  Dora lived with her daughter in Chase City until her death in 1898.  

Pineland burned in 1910.  Clarence Broocks Jr, grandson of Charles and Dora Robertson bought the old home place in 1951. The stone wall still stands that was built in front of the original Pineland in front of the new house.

To clarify that article a little more.  Clarence Broocks Robertson Jr son of Charles and Dora

Article on the Robertson family of Pineland by Galen & Nancy Harrison

Civilian Flag of Truce Cover from Pineland Plantation, Wyllicsburg, Va.


By Galen & Nancy Harrison

 In our last outing we detailed our discovery of a previously unknown Andersonville, Prison cover. In this article we present our study of a cover once thought to be an Andersonville, Prison cover, but which is actually something entirely different. The cover as seen in Figure 1, addressed to Miss P.M. Judd, West Hampton, (sic) Massachusetts is a South to North through the lines cover bearing postage of both sides. Or at least it bears the remnants of Confederate postage in the form of a pair of C.S. #7s along with a 3 cent rose #65 for U.S. postage. The pair of C.S. #7s were originally applied over a coin, probably a half dime, to pay for U.S. postage. The envelope used was a demonetized 3 cent 1861 Star Die. Figure 2, shows detail of the postal usage. The addressee, Miss P.M. Judd we determined using U.S. Census records and vital records of Westhampton, Massachusetts was Princess Mariah Judd, born June 6, 1826 at Westhampton, Massachusetts. The addressee's name also appears in some documents and listings as Princess Mary Judd.

Our study of this cover began when we first saw it described for sale in a Robert Siegel auction catalog. It was described as being from the Confederate Prison at Andersonville, Georgia. To us it seemed unlikely that a prisoner at Andersonville would have had in his possession or, would have had access, to the three things that were used to post this cover. Those three things were, a no longer valid 3 cent Star Die, a pair of 5 cent C.S. #7s, and a coin to pay for the 3 cent rose #65. A close look at the cover reveals proof the cover is not from Andersonville. The CDS is Old Point Comfort, Va. Oct. 3rd. While the year date is not shown, it was not difficult to determine. The U.S. stamp is tied with a poor but recognizable strike of a target cancel. Figure 3, shows an example of a complete strike of this cancel. This target cancel was used the entire month of October of 1863; and was not used in October of any other Civil War year. The first prisoners arrived at Andersonville on or about February 1, 1864, which would have been approximately four months after this cover was used through the lines. We contacted the Siegel firm and explained our reasoning, as did another prominent dealer and collector. The cover was withdrawn and re-offered as a probable civilian flag of truce cover. We were the successful bidders.

It wasn't from Andersonville then, but could it have been from another prison? We didn't know, but we didn't think so. Trying to determine the author of a cover addressed to a "Miss" can be a very difficult. We started by looking at the Judd family of Westhampton, Massachusetts. The 1850 Census of Hampshire County, Massachusetts town of Westhampton showed a family headed by Eleazer Judd, age 63, his wife Dora was the same age. Two children were still living at home, a son, Eleazer, Jr. 29, and a daughter, Princess M. 23. Luckily for the purposes of our story, the state of Massachusetts was keeping birth and marriage records by this time. On a page headed, "MARRIAGES registered in the Town of Westhampton for the year 1848." which incidently was kept by Town Clerk John A. Judd, we found the marriage of Dorothy L. Judd, daughter of Eleazer & Dolly Judd.  She was married on July 3, 1849. The surprising thing was that she did not marry a local. She married Charles H. Robertson, Planter of Charlotte, Virginia. It was a first marriage for the bride; it was the second marriage for the groom. John Adams Judd, the Town Clerk, was a merchant, and also the postmaster at Westhampton. He was the bride's uncle. The Congregationalist Minister, Jonathan S. Judd who performed the ceremony was the bride's brother.

We had in effect found a puzzle within a puzzle. Why would a planter from Charlotte, Virginia go all the way to Massachusetts to marry a woman from there? How had they even met? It was time to look at census records again. The 1850 census of Bacon District, Charlotte County, Virginia shows the new Robertson family, Charles H. and Dora had six children by Robertson's first wife living at home. And the newlyweds had a 3 month old daughter of their own. On the 1860 census, Charles H. Robertson and Dorothy or Dora as she preferred reported a net worth of over $120,000. The 1860 slave census showed them with 58 slaves. We found it interesting that the Robertsons lived in Bacon District of Charlotte County, Virginia because each time we travel between home and Richmond we see a small sign that says "Bacon District". The sign refers to the school district but it was what caused us to decide to go to Charlotte County to research this cover.

We contacted the Charlotte County Historical Society and after receiving assurance of their hours of operation we made a day trip there to see what we could learn. We were met there by Ms. Bea King who had prepared for us an information folder on the early Robertson family. She was able to show us on the county map the area where the Robertson family place was located, appropriately on Robertson Road in Wylliesburg, Virginia. She provided information from the Charlotte County Heritage Book. We learned that Pineland Plantation with 2000 plus acres was owned by Charles Henry and Margaret F. (Peggy) Robertson until her death in 1846. We also learned that Dora L. Judd had been hired from Massachusetts in 1844 to teach neighborhood children. Miss Judd resided with the Zachariah Bugg family on the adjacent plantation.

The following day using the information we were provided at the historical society we drove to Wylliesburg where we had been advised direct descendants of Dolly Judd Robertson resided. With a certain amount of trepidation we knocked on the doors at two different houses which had been pointed out to us as being the homes of Robertson descendants. We need not have been concerned; we were made us feel comfortable after we explained the reason for our visit. Mrs. Tammy Hinchey, the first lady we met talked readily with us about the early Robertson family and even made us copies of some of the material she had in reference to her ancestors. She suggested however that her cousin who lived perhaps half a mile away knew more than she did.

At our second stop of the day we met Mrs. Kay Pierantoni, another direct line descendant of Dora Judd Robertson. She was the very epitome of southern hospitality. She was able to give us the full story of how Charles Henry Robertson, a Virginia Planter came to travel to Massachusetts to marry Dora Lyman Judd. It went like this: in 1844 Dora Judd had come down from Massachusetts to Bacon District of Charlotte county as a teacher for the children of that neighborhood. She became a close friend to Margaret (Peggy) Robertson, Charles Henry Robertson's first wife. The two women became much like sisters. When Margaret became sick in 1846 and knew she was about to die, she made a request to Dora, that after her death, Dora would marry Charles and take care of her children.

According to the family, Charles wanted that to happen shortly after Margaret died, but Dora apparently did not think it was appropriate to marry Charles that quickly. For that reason she returned to Massachusetts. Charles not one to give up easily wooed Dora, via U.S. Mail. Charles got some help from Zachariah Bugg who also wrote to Dora to speak of the love Charles felt for her. Dora eventually accepted Charles proposal and they were married in July 1849. We were convinced our cover was from Dora to her sister Princess Judd. The single concern we had as to the correctness of our hypothesis that Dora Judd Robertson had written the subject cover to her sister was upon learning Dora Judd was a school teacher and yet had addressed the cover to Princess spelling Westhampton as West Hampton. She was born and raised there, surely she would know the correct form of the town name. The answer to that was in a letter, actually a "P.S." to the letter in which Dora wrote to Charles to accept his proposal. She wrote, "P.S. Your letters to me have twice been missent - perhaps if you should write West Hampton with two capitals they would be less liable to it. D.L.J." Two documents written by Dora proved the handwriting was the same as that on the subject cover. It is highly likely the cover was mailed at Wylliesburg, Virginia where Dora and her family now lived. It was fairly common for local Confederate Postmasters to omit the town names on through the lines mail where only one envelope was used. The postmaster at Wylliesburg at the time was Ludwell Barnes who would have been a cousin of Charles H. Robertson's first wife.

The Civil War did not lay waste to the Bacon District of Charlotte County, Virginia as it did to many areas of Virginia. But that did not mean the Robertson family and Pineland Plantation were spared hardship however. All five of Dora's step sons served in the Confederate Army; four came home, Henry died at Shepherdstown, Virginia. From time to time patrols from either army would approach the plantation and take whatever they could. And of course the slaves that had produced as much as 30,000 pounds of tobacco in 1860, were now free. A interesting document still in the possession of the family offers a glimpse into what kind of man Charles Henry Robertson was. Figure 4, shows a copy of a contract. That contract shows that Robertson went to the Freedman's Bureau in Richmond on January 31, 1866 and hired seven of his former slaves to help him with farm work.

We don't know exactly when Princess Judd came down from Massachusetts to live with Charles Henry and Dora Robertson. We can offer a basic time line for the move. We know Dora wrote her sister probably late September 1863, the cover seen in this article. Eleazer Judd her father died June 13, 1863. Dolly Lyman Judd their mother died 3 August 1866. And we know Princess Judd was listed on the 1870 census of Charlotte County living in the household of Charles Henry and Dora Robertson. The move was a permanent one on her part. She is buried in the Robertson Family Cemetery in Wylliesburg. Figure 5, shows the stone over her final resting place.

Authors note: We could not have written this without the help of Bea King from the Charlotte County Historical Society, and the mentioned descendants of the Charles Henry & Dora Judd Robertson family.