Tracing the lineage of Thomas Woollen Sr and Elizabeth Pagan Woollen of Dorchester County, MD

How do you figure out family relationships when there aren’t marriage records, family bibles, or a full set of probate or census records?

The answer is land records.

In my case, I was trying to find the parents of Mary Woollen who married William Webster in 1834, Washington, DC. I found their 1840 and 1850 census records in Northumberland County, VA, and a land record where Mary was claiming her dower rights in Northumberland in 1854. So, I knew William Webster had died December 1853 in Northumberland, VA.

Turns out, she is the daughter of John Woollen and Henrietta Harris, and the granddaughter of Thomas Woollen Sr and Elizabeth Pagan of Dorchester County, Maryland. If you’re on Ancestry, you can see her tree here.

Read on for the full story of how this ancestral line was “proven”…

Here are the key family members in this blog post

• Thomas Woollen Sr and his wife, Elizabeth Pagan. All the land I tracked came back to this couple. Most of the land they inherited from their parents or purchased from their siblings.
  • Their children in birth order: Mary Woollen who marries Levin Gadd (referred to in this blog post as “Mary Woollen Gadd”), John Woollen (he has an Uncle John who is noted in the blog post as John 1), Thomas Woollen Jr, James Woollen Sr, and Robinson Woollen.
  • Elizabeth Pagan’s father, John Pagan, and her siblings: Mary, Sarah, Jane and Priscilla Pagan. John Pagan originally owned two tracts of land called Hazzard and Hazzard’s Desire.
• Thomas Woollen Sr’s parents: John Woollen Sr (let’s call him John 1, as he has a son and grandson also called John) and his wife Lettice Cummins
  • John and Lettice Cummins Woollen’s children: John Jr (“John 2” in the post), William, Edward, Thomas (“Thomas Sr” in this post), Jane, Roger, Levin, Job Woollen.
• John Woollen Sr’s parents: Edward Woollen and Jane Pollard.
  • Jane Pollard’s father, John Pollard, who originally owned a tract of land called Hallowing Point.

By following the land sales of Hazzard, Hazzard’s Desire, and Hallowing Point, we can piece the families together.

About William Webster and Mary Woollen

This is the couple I’m researching. I have all the information on William Webster from Prince George’s County, MD, but who was Mary Woollen, and who were her parents?

Interestingly, I used a court record to prove the family of William Webster here, but didn’t know his wife’s Woollen family at all.

William and Mary married in 1834, in Washington, DC. They are on the Northumberland, VA tax and census records from 1835 to 1854, when the widow Mary Woollen Webster claims her dower rights to land in Northumberland, VA. When their daughters married in Baltimore, MD four years later, they are noted in newspaper announcements as being from Northumberland, VA.

William and Mary Woollen Webster had five children, three of whom lived to adulthood. All three daughters married in Baltimore City, Maryland: Amanda Webster married John Lavine in 1858, Cornelia Webster married William Allen in 1858, and Frances Webster married William’s brother, John Thomas Allen in 1872 (she is living with her sister Amanda in 1860 and there doesn’t seem to be a parent nearby).

The 1850 census says that Mary Woollen Webster was born in 1812, in Maryland.

But what happened before 1854? Who were the Woollen grandparents of Amanda, Cornelia and Frances? 

First, finding the Woollen families in Maryland

There aren’t many Woollen families in the USA at this time, and those in the region are almost exclusively from Dorchester County, MD and Baltimore, MD. That gave me my first clue.

I re-created every Woollen family I could find in Maryland, and followed all the DNA matches, but still couldn’t find my Mary Woollen who was born in 1812 Maryland.

Two Woollen family biographies were created in the mid-1980s when the internet was in its infancy: “We Woollen” was written by Keith Coy Woollen sometime around 1985. “Woollen/Woolen Family Biographical and Historical Records” was written by Edward A. Woolen in Richmond, VA in 1984. Each man was writing about a different family line of the Maryland Woollens, and both books include a slew of Maryland land records. They’re available in PDF format from the FamilySearch website. In this blog post, I’ll refer to them as We Woolen and Woollen Bio so you know where to find the records.

Both books are full of records — but, unfortunately, full of assumptions about family relationships that can lead a researcher astray.

Note that the surname is spelled differently in records: Woollen, Woolen, Woollin, Wooling, Wollen

I went back through the records and found one Woollen man who was in Northumberland VA: John Woollen from Dorchester, MD, who moved first to Baltimore, and ends up in Northumberland, VA around 1824. 

If John Woollen was in Northumberland in 1824 and Mary Woollen Webster was in Northumberland starting in 1835, were they related?

DNA pointed in this direction, but I needed records to prove it.

Let’s follow the land sales to make the family connections

Here are the records for Thomas Woollen of Dorchester County, MD who married Elizabeth Pagan — and how the land went from his Woollen family, and her Pagan family, down to this John Woollen from Dorchester, MD and Northumberland, VA, and his siblings: Mary Ann Woollen Levin, James Woollen Sr, Thomas Woollen Jr, and Robinson Woollen.

I’ve bolded the tract names so you can follow along.

I was able to trace all these transactions to discover my Woollen family line: Edward Woollen m. Jane Pollard>John m. Lettice Cummins (“John 1” in the records below)>Thomas m. Elizabeth Pagan (“Thomas Sr”)>John Woollen m. Henrietta Harris>Mary Woollen m. William Webster>Cornelia Webster m. William Allen>Anna Catherine Allen m. Henry Presser>etc.

All of these transactions occur in Dorchester County, MD until 1824 when John and Henrietta Harris Woollen move to Northumberland, VA. Most of the records are for the area of Dorchester, MD known as Taylors Island, an island off the eastern shore of Maryland separated from the mainland by the Slaughter River coming in from the north and the Upper Keene Broad coming in from the south, and bounded on the west by the Chesapeake Bay. It’s low-lying land with a lot of marshland; the land is still very agricultural today. 

• 1662
  • Taylors Island was one of the first settlements in Dorchester County, Maryland when the Taylors took ownership of 400 acres of land on the island.
• 1683
  • John Pollard gets a tract of land called Hallowing Point, 100 acres. He also gets Herring Point, Obscurity, and several other tracts of land. Some online sites say he got this land 1679, not 1683. But the book, Settlers of Maryland, say 1683. Maybe he surveyed it in 1679 and patented it in 1683.
• 1700
  • John Pollard writes a will in Dorchester County, MD, leaving land to his grandchildren (children of his daughter Jane Pollard who married Edward Woollen)
    • To my daughter, Jane, wife of William Robson Jr, 100 acres, Cedar Points; another 100 acres purchased called Mattikin; 100 acres called BloodPoint. Jane first married Edward Woollen, and upon his death, married William Robson Jr. That’s why she’s called Jane Robson in her father’s will. She has two Woollen children and one Robson child.
    • To granddaughter Ann Wooland (Woollen), 100 A., Herring Point on a branch of the Blackwater River. Note this is Herring Point, not Hallowing Point. But at some point in time, Hallowing Point is in the possession of John Woollen 1, who sells it to his brother, Thomas Sr, so John 1 must have inherited both tracts from his Pollard grandfather.
    • To granddaughter Mary Robson and heirs, Obscurity to pass at her death to her brother John Wooland (Woollen). Mary Robson is the daughter of Jane Pollard and her first husband, William Robson. She is born 1695 and later marries Henry Keene. When she dies in 1750, Obscurity passes to her half-brother, John Woollen 1.
  • When William Robson Jr owned a tract of land called Hazzard. He married the widow Jane Pollard Woollen after her first husband, Edward Woollen dies (son of John 1), After William Robson Jr dies, she inherits Hazzard, and it is passed down to her children.
  • Woollen Bio says Hallowing Point was mentioned in John Pollard’s will, but I don’t see it mentioned. It’s still a bit of a mystery how Hallowing Point passed from John Pollard to his grandson, John Woollen 1.
    • https://www.genealogy.com/ftm/h/a/c/None-None/WEBSITE-0001/UHP-0056.html
• 1728
  • From John Woollen (“John 1”) and Lettice Cummins Woollen, to John Barns, part of Commencement adjoining Hallowing Point and Davises Chance (I don’t think the Woollens own Davises Chance, just noting that Commencement adjoins it).
    • This is John Woollen 1, son of Edward and Jane Pollard Woollen. He is born about 1697 or earlier to be old enough to sell land in 1728.
    • This tells us Commencement and Hallowing Point are tracts of land situated next to each other.
    • How does he get Hallowing Point and Commencement? A mystery to be solved. John Pollard owned Hallowing Point first. I’m not sure who originally bought Commencement.
• 1751
  • John Woollen 1 writes a will in 1751, Dorchester County, MD, and names his children: John Jr (“John 2” in the post), William, Edward, Thomas (“Thomas Sr” in this post), Jane, Roger, Levin, Job. The surname is written as Woolling.
  • • Since John Woollen 1 only sells part of Commencement in 1728, he still owns part of it. His will reads:
    • To my loving wife, my dwelling plantation Hollowing Point (aka Hallowing Point) during her natural life or widowhood, likewise part of the Comminsments (sic Commencement) which belong to me.
    • To son John Wolling, Hollowing Point and that above part of ‘Consignments’ (sic Commencement) after my wife’s marriage or decease.
    • Two sons John Wolling (John 2) and William Wolling Hollowing Point and the land lying on Blackwater called The Herring Point, the division to be between them. (This is Herring Point which John Pollard left to John Woollen 1 and his sister Mary Robson in 1700)
    • Job, son of John 1, does not marry and later leaves a will, devising his estate to some of his siblings: Jane Woollen Aaron, Levin Woollen, Molly Woollen (who later marries Zephaniah Taulbee)
• 1752
  • Thomas Woollen Sr, age 54 (b 1728) testifies about a boundary between his father’s land and the Travers’ family land, Taylors Folly.  Also mentioned, some of the other early settlers, like Page, Robson, Patterson, etc.
    • This is Thomas Woollen Sr, son of the above John Woollen and Lettice Cummins. He married Elizabeth Pagan. 
    • The tract of land they’re discussing in this boundary case is called Taylors Folly, the tract of land owned by Matthew Travers and devised to his son William Travers in 1741. So the Woollens and Travers are neighbors.
    • https://archive.org/details/vanishingislands0000kola_v5f6/page/28/mode/1up?q=%22thomas+woollen%22
• 1754
  • From John Woollen 2 (m. Elizabeth Unknown) deeded Hallowing Point (note the name change from Hollowing Point to Hallowing Point) and part of Commencement (adjoining each other) on Taylors Island to Thomas Woollen Sr.
    • This is land John 2 inherited from his father, John 1, in 1751. He is selling Hallowing Point and part of Commencement to his brother, Thomas Sr.
    • John 2’s wife, Elizabeth,  acknowledges this land sale. She is the executor of John 2’s estate in 1765, and names his children in the estate records. I don’t have a maiden name for her.
    • In the Woollen Family Bio book, image 245
    • Hallowing Point contains 100 acres. This is important to note. There are many land sales involving Hallowing Point, but always small parcels: 2 acres here, 7 acres there. They have a lot of land they can sell!
    • Commencement, beginning at division tree with John Woollen and John Barnes, 50 acres. This is the division tree mentioned in the testimony of Thomas Woollen Sr in 1752.
    • This is Thomas Woollen Sr and Elizabeth Pagan Woollen buying this land from John 2. Later, their children and grandchildren sell these tracts.
    • It’s unknown who John 2’s wife’s maiden name. Some hypothesize Travers, since they live next door. She is not named in Matthew Travers will, so if she is a Travers, her father is not Matthew. John Barnes also lives next door.
• 1760
  • Thomas Woollen Sr (m. Pagan) purchases Thomas’ Desire in Dorchester. This land was later sold by his son, John.
• 1762
  • Mary Woollen is born to Thomas and Elizabeth Pagan Woollen on 2 Feb 1762. She has a christening record in Dorchester Parish Episcopal Church.
• 1763
  • John Woollen is born to Thomas and Elizabeth Pagan Woollen on 8 May 1763. He has a christening record in Dorchester Parish Episcopal Church
• 1765
  • Thomas Woolen, Jr is born to Thomas and Elizabeth Pagan Woollen on 15 Jul 1765. He has a christening record in Dorchester Parish Episcopal Church. (There are no christening records for the next two sons, James and Robinson, but Thomas Jr names them as his brothers in his 1821 will.)
• 1770
  • James Woollen Sr is born to Thomas and Elizabeth Pagan Woollen. His birth year comes from his gravestone.
• 1781
  • Thomas Woollen Sr helps establish the Methodist Church in Dorchester. This might be why there are no Episcopalian christening records for James or Robinson.
  • Robinson (Robison) Woollen is born to Thomas and Elizabeth Pagan Woollen sometime between 1781-1784. Clearly, there is a big gap between the births of James Sr in 1770 and Robinson which needs to be explored.
• 1783
  • Family taxed on their tracts and land
  • https://msa.maryland.gov/msa/stagser/s1400/s1437/html/1437do.html
• 1785
  • The Pagan sisters and their spouses divide their parents’ land after their father, John Pagan, dies.
  • January 1785
    • From Thomas and Elizabeth Pagan Woollen, Joseph and Mary Pagan Travers, Thomas and Sarah Pagan Harris, Jacob and Jane Pagan Travers, and Priscilla Pagan, to Henry Hooper, selling a tract of land called, Lucy’s Ridge, Taylors Island, 35 acres. This must be John Pagan land.
  • March 1785 division of the land of John Pagan, deceased, between his heirs:
    • John Pagan is Elizabeth Pagan Woollen’s father – she marries Thomas Woollen Sr
    • John Pagan’s estate and land division record names his daughters and their spouses, and notes the order of birth of his daughters:
    • To Thomas Woollen who married Elizabeth the eldest daughter of the dec’d, part of two tracts called Hazzard and Hazzard’s Desire. So Thomas Woollen Sr is still alive in 1785. This is important because some online trees say he dies before this. Thomas’ children would later sell these tracts.
    • To Joseph Travers who married Mary, the second daughter of the dec’d, the remaining of Hazzard and Hazzard’s Desire, and part of Aaron’s Folly.
    • To Priscilla Pagan, third daughter of dec’d [unmarried], part of two tracts called Pilgrim’s Rest and Aaron’s Folly.
    • To Thomas Harris who married Sarah, the fourth daughter of dec’d, the remainder of Pilgrim’s Rest and Aaron’s Folly and a tract called Prissey’s Marsh.
    • To Jacob Travers who married Jane, the youngest daughter of said Pagan a tract called Pilgrims Progress with 6.5 acres lately included in a resurvey of the said tract.
    • Also in 1785, deposition of Edward Woollen aged 60 was present at the above resurvey of the land tract. (b 1725, son of John 1 and Lettice Cummins, brother of John 2 and Thomas Sr, also named in his father’s will.)
• 1791
  • Mary Woollen marries Levin Gadd in Dorchester. She is the daughter of Thomas Sr and Elizabeth Pagan.
• 1793
  • February 1793 – Elizabeth Pagan Woollen buys Wollen’s Possession on Taylors Island from Moses LeCompte.
    • This is Elizabeth Pagan Woollen because her children Mary and John later sell this same land.
    • Thomas Woolen Sr must be dead by this time, as she buys the land on her own.
    • 41.5 acres.
    • The We Woollen and Woollen Bio books aren’t clear about this land purchase but says this is John 2’s daughter Elizabeth who marries Reubin North. She marries in 1798, aged 44 (Reubin North is born 1775-1784, so I doubt this Elizabeth is right wife for him, but that’s another story!). But if it’s Elizabeth m. North who buys Woollen’s Possession in 1793, why would our Mary and John sell it later? It’s not even the same family line. I think the book is incorrect and it is Elizabeth Pagan Woollen who buys this land, not the unmarried Elizabeth Woollen who later marries North. Like I said, We Wollen makes a lot of assumptions about which family members are connected to each other, some of which don’t make logical sense.
    • Elizabeth Pagan Woollen seems to live until at least 1800. She appears to be living with her son, John, in the 1800 Dorchester, MD census.
• 1796
  • James Woollen Sr marries Elizabeth Rix in Baltimore City. He is the son of Thomas Sr and Elizabeth Pagan. His gravestone says he was born 1770. Later Thomas Jr, his brother, devises a tract of land to James Woollen Jr, “son of my brother James.” (Thomas also devises a tract of land to “Thomas, son of my brother Robinson,” cementing that Thomas Jr, James and Robinson are brothers.)
• 1798
  • See image 248 in Woollen Bio book, and the complete land transactions.
  • 10 Apr 1798 – From William Keene of Henry and Kitturah his wife, to John Woollen of Thomas. Tract called Johns Fortune, 147 acres. The record literally says “John Woollen of Thomas”
  • 12 Apr 1798 – John Woollen of Dorchester to William Keene, Johns Fortune, 147 acres. 
  • Both of these transactions are acknowledged before an associate judge. 
  • Why would he buy this land then two days later sell it back? Are they trying to clear the title? Or are they simply swapping twin tracts?
    • 1783 Kiturah is taxed on this tract. William Keene is the agent. I’m guessing he later marries her.
      • Kiturah Barns. Johns Fortune, pt, 88 acres. Notes: William Keene of William, agent. DO Lower District Hundred, p. 37. MSA S 1161-5-4    1/4/5/48
      • William Keene, of William. Johns Fortune, pt, 88 acres. Notes: for Kiturah Barns. DO Lower District Hundred, p. 37. MSA S 1161-5-4    1/4/5/48
• 1799
  • 1799 Reubin North of Dorchester and Elizabeth his wife, two tracts, “Last Purchase” tract 40.5 acres, and “Johnsons Last Purchase” 8.75 acres.  Described in a deed from Charles Shenton to John Woollen. (Last Purchase bought by John Woollen 1 in 1762)
    • I’m putting this here to show there is another John Woollen, and his daughter Elizabeth Woollen North, existing in Dorchester at this time. This is John Woollen 2 and his daughter. He’s dead by 1799 (he dies in 1765-ish). This could be why some records say “John Woollen of Thomas” to distinguish him from the other called John Woollen living in Dorchester at this time.
• 1800
  • Elizabeth Pagan Woollen dies after 1800. She is on her son John’s 1800 census in Dorchester. In 1802, John goes to Baltimore and runs a grocery business. The children begin selling the land they inherited from their parents in 1807. Unless John takes his mother with him to Baltimore, it’s safe to assume she dies sometime between 1800-1807.
• 1805
  • Robinson Woollen marries Hannah Catts in Baltimore City. He is the son of Thomas Sr and Elizabeth Pagan. He, James and John are all living in Baltimore at this time and show up in the Baltimore City Directory.
• 1807
  • John Woollen’s last listing in the directory is 1807, though there is an 1810 Woolen and Darrington Grocer which might be his firm. You can see why there are no further listings, as he’s now in Dorchester per this land record.
  • From John Woollen of Thomas of Dorchester, to Levin, Risdon, John, Margaret, Martha and Henrietta Harris (aka Harriss) of Dorchester, part of Hallowing Point on Taylors Island, 12 acres.
    • The record says “John Woollen of Thomas”
    • The following year, John Woollen marries the same Henrietta Harris who just bought his land.
    • The record does not say the land sale is acknowledged by a wife, so he is unmarried in 1807 when he sells this land.
    • The We Woollen book comments that the Harris people are all siblings. I don’t know if that is true, but could married women buy land in their own name in 1807? Single women and widows could. Later there are land transactions that mention Levin Harris and Margaret Harris, so it’s possible they are all siblings.
• 1808
  • John Woollen marries Henrietta Harris in Dorchester County, MD. He is the son of Thomas Sr and Elizabeth Pagan. Yes, he’s 45 years old, and it is his first marriage.
• 1809
  • From John Woollen of Dorchester to Thomas Woollen of Dorchester, part of Hallowing Point
    • acknowledged by John Woollen and “Henny” his wife.
    • This is John Woollen who married Henrietta Harris the previous year, son of Thomas Sr. He is selling part of Hallowing Point to Thomas Jr, his brother. Thomas Jr later devises this tract to his nephew in 1821.
• 1811
  • 8 Jun 1811
    • There are a lot of transactions here, where the family is selling bits of land to each other. See image 249 in Woollen Bio book.
  • 8 June 1811, from John Woollen, Thomas Woollen Jr, Levin and Mary Woollen Gadd (all of Dorchester), and Robinson Woollen of Baltimore, sold part of Hazzard and “Hazzard’s Desire” and “Woollen’s Possession” adjoining “Hallowing Point” to James Woollen Sr of Baltimore (their brother) – 26 acres.  (image 25)
    • Acknowledged by John Woollen and his wife, Henrietta, and Robinson Woolen and his wife Hannah. This is John m. Harris and Robinson m. Catts.
    • John, Mary, James and Robinson are all siblings. They are selling part of the land they inherited to their brother James.
      • We Woollen makes assumptions that Robinson is the son of John. But Thomas Jr clearly says that Robinson is his brother, not his nephew. Robinson, Thomas Jr, James Sr, Mary Woollen Gadd, and John Woollen (of Thomas Sr) are all siblings.
• 1815
  • Jane (sic – JAMES) Woollen of Baltimore sold Hazzard’s Desire and Woollen’s Possessions, 10.75 acres
    • acknowledged by James Woollen and wife Elizabeth. This is James Woollen who married Elizabeth Rix in 1796.
    • This is James selling part of his inheritance from his father Thomas Sr.
• 1818
  • 7 March 1818 – from John Woollen of Dorchester to John Recarrd, part of Hallowing Point, beginning near Thomas Woollen’s house and Ferry Point house. 2 acres.
    • Acknowledged by John and wife Henrietta.
• 1821
  • Thomas Woollen Jr of Taylors Island, Dorchester, MD writes a will. He never marries so devises his property to his nephews.
  • The will is proven in 1829.
  • He devises Hazzard to James [Jr], son of my brother James [Sr].
  • He devises “my home place on Taylors Island” to Thomas, son of my brother Robinson.
    • James Woollen Sr dies in 1852. In 1849, James Woollen Jr gets a passport; there are no further records for him. What happens to the land that James Woollen JR inherits from his uncle Thomas?
• 1822
  • 14 Dec 1822 – From John Woollen of Dorchester to Jeremiah Spicer of Dorchester. Parts of Lazzarus Desire (sic Hazzard Desire) and Woollen’s Possession, on the west side of Commencement, part of the land he received in the estate of his mother, Elizabeth (Pagan) Woollen, also part of Lot #1 containing 7 acres.
    • This is the first time I’m hearing about a tract of land called Lot #1. Typically the word “lot” is used to denote land inside a town boundary.
  • 25 Oct 1822 – From John Woollen and James Harrington to John C Travers, a tract called Harris Beginning.
    • James Harrington married Margaret Harris, Henrietta Harris’ sister, in 1815. James Harrington does not have an 1820 census in Dorchester.
    • I’m assuming this is land Henrietta and Margaret Harris inherited from their father, William Harris. I need to research Harris Beginning to see how it came into their hands.
    • We Wollen speculates John C Travers’ wife might be a Woollen. But this appears to be John Critchett Travers who marries Mary Dove and she’s 19 when she marries. This John C Travers is probably a son or grandson of Matthew Travers, the Woollen’s neighbor.
• 1823
  • An 1823 land record mentions a division line established in 1785 between Thomas Woollen and Joseph Travers, both sons-in-law of John Pagan.
• 1824
  • There are a lot of land transactions in 1824 and 1825 as John is preparing to go to, or is living in, Northumberland, VA.
  • Woollen Bio book, image 294
  • 2 Sep 1824 – From John Woollen of Dorchester (not Northumberland) deeds part of Hallowing Point to Robinson Woollen of Baltimore, adjacent to Thomas Woolen’s lot. 
    • Ack John and Henrietta. 13.25 acres. It does not say that John is the father of Robinson, though We Woollen speculates this. They are brothers.
  • 2 Sep 1824 – From John Woollen of Northumberland, VA to John C Travers of Taylors Island, parts of Hallowing Point, Commencement, Woollen’s Possession and Thomas’ Desire (Thomas Woollen Sr’s original land from 1760)
    • totaling 170 acres. Acknowledged by John and Henrietta Woollen.
    • We can see that John Woollen and his wife, Henrietta Harris Woollen have moved to Northumberland, VA by this time. He has tax records there from 1824-1839, aka “John Woolling.” See the year 1834 for the tie-in.
  • We Wollen says Robinson was deeded Hallowing Point “from his father, land that adjoins his father’s brother Thomas.” That makes Thomas who dies in 1829 the brother of John, not his son. But the record doesn’t actually say “his father” — it only lists the people. This is We Woollen’s incorrect interpretation of the people in this transaction.
• 1825
  • 26 Oct 1825 – From John Woollen of Northumberland, VA to Jeremiah Spicer and Thomas Woollen, slaves
  • 20 Dec 1825 –  Levin M. Harriss and John Woollen of Dorchester to Jeremiah Spicer, part of Aaron’s Regulation on St John’s Creek, 37.75 acres.
    • How would John have gotten this land? Is this Henrietta Harris’ father’s land? Levin M Harris is Henrietta’s brother. He buys John Woollen’s land along with his siblings in 1807. So, I’d guess that Aaron’s Regulation came through the estate of Henrietta and Levin Harris’ father, William Harris. Another land tract to research later!
  • Note: I couldn’t find John Woollen buying land in Northumberland, VA, though he is on the personal property tax records there from 1824-1839. He’s just sold a huge amount of land in Dorchester, MD. What does he do with all that money?
• 1827
  • 18 Aug 1827 – From Mary Woollen Gadd of Dorchester to Robinson Woollen of Baltimore, part of Hazzard, Hazzard’s Desire, and Woollen’s Possession.
    • This is Mary, daughter of Thomas Woollen Sr and Elizabeth Pagan. She is selling part of the land she inherited to her brother, Robinson.
    • Levin Gadd must have died by this time, as she is selling the land in her own name.
  • 25 Oct 1827 – From John Woollen and Henrietta his wife of Northumberland, VA to Jeremiah Spicer of Dorchester County, MD.
    • Their interest in land bought by said Spicer from Levin M. Harriss on Taylors Island called Aarons Regulation containing 37.75 acres. This is the land they sold in 1825. They must have given Spicer a mortgage, which he has paid off, therefore they no longer have a legal interest in the land.
• 1829
  • Thomas Woollen Jr dies in Dorchester. His nephews James and Thomas would have inherited his land.
• 1833
  • 8 May 1833 – From Robinson Woollen and Hannah his wife of Baltimore, sells part of Hazzard, Hazzard’s Desire and Woollen’s Possession adjacent to Hallowing Point,
    • Also selling lands of Levin Gadd (Mary Woollen Gadd’s husband) on St. John Creek.
    • Also sold 10 acres on Taylors Island
    • This is Robinson, son of Thomas Sr and Elizabeth Pagan. He’s selling Levin Gadd’s land; does this mean he has inherited it from his sister? Or simply it’s a notation that this is the land he bought from his sister in 1827? I’d have to see the original land record to be sure.
    • To Moses Navy of Dorchester County
    • We Woollen image 25.
    • Woollen Bio image 424.
• 1834
  • Mary Woollen marries William Webster in Washington, DC
• 1835
  • Both John Woollen and now William Webster show up on the Northumberland VA tax list. Therefore I can assume with some certainty that Mary Woollen who married in 1834 is the daughter of John Woollen and Henrietta Harris. Note that these land locations are all across the Chesapeake Bay and Potomac River from each other: Taylors Island in Dorchester, Northumberland, VA (they live near Lewisetta on the northern coast of Northumberland), Baltimore Maryland, and Washington, DC. Once you see it on a map, then it makes sense that she married in Washington DC where William Webster’s family lived, but lived in Northumberland, VA.
• 1836
  • 4 Nov 1836 – to William Webster from Griffin H Foushee, Book 29, page 230, 1/3 part of Hog Island in the Coan River, Northumberland, VA
• 1840
  • William Webster on Northumberland, VA 1840 census with an older woman. His mother is already dead, so this is likely Henrietta Harris Woollen, Mary’s mother.
• 1844
  • 25 Apr 1844 – from William Webster to Richard A Claybrook and William Cowarth, all of Northumberland, VA. An island at the mouth of Coan River upon which Webster now resides called Hog Island
• 1850
  • The William Webster family on the 1850 Northumberland VA census.
• 1854
  • Mary Woollen Webster claims dower rights to land on Hog Island in Northumberland County, VA. She says her husband died in December 1853.

Voila! 🙂 Mary Woollen Webster was the daughter of John Woollen and Henrietta Harris. I feel fairly confident about this one.