Mary Benson (c1675–c1758) Heiress of Crackbornes Purchase in Leonard’s Town – 52 Ancestors #383

Mary Benson was born to Hugh Benson sometime after his 1671 immigration, probably between 1673 and 1678 in St. Clements’s Hundred. Her mother’s name was Catherine.

St. Clement’s Hundred was defined as St. Clements Island and 5 miles into the mainland of present-day Maryland.

Mary was married to Bowling Speake sometime before March 31, 1739, when they conveyed land that she inherited from her father to Thomas Spalding.

Bowling Speak was born in 1674, so it’s likely that Mary was born around the same time. She would have been about 65 years old in 1739.

Were it not for that deed, we would have no link to the identity of Mary’s father.

Archives of Maryland, Volume 42, Assembly Proceedings, May 26-June 22, 1741.
The Lower House. Page 212; Liber L. H. J., Page 272: (Saturday Morning June 6.
1741) By the Committee appointed to enquire into the Facts contained in the Petition of Thomas Spalding and Catherine his Wife June the 6. 1741

Your Committee find on Inspecting the Papers of the Petitioners that the Land called Crackbornes Purchase containing 200 Acres was Granted on the 24th day of October Anno Domini 1659 unto Richard Crackborne Assignee of Walter Peak and Peter Mills Assignees of Paul Simpson in Fee.

Your Committee further find that the said Richard Crackborne by his Deed bearing date the 17th day of November 1681 did Bargain and Sell the said Tract of Land to Richard Gardiner of Saint Marys County in Fee Your Committee also find that Richard Gardiner and Elizabeth his Wife of St. Marys County aforesaid did Convey to Hugh Benson of the same County Planter 100 Acres Part of the said Tract in Fee [p. 273]

Your Committee likewise find that Mary Speake is the reputed Daughter and Heiress at Law of Hugh Benson and that she intermarried (as it is said) with Bowling Speak of Charles County and that the said Bowling Speak and the said Mary his Wife, by their deed Bearing date the 31st of March 1739 did Convey the said Parcell of Land unto the Petitioner Thomas in Fee All which deeds appear to Your Committee to be duly Executed Your Committee further find by the Information of W James Swann a Member of your House that the Land called Crackbornes Purchase mentioned by the Petitioners to be Granted is of greater Value than that Part of the Land the Petitioners pray to be enabled to dispose of called Seamour Town or known by the name of Leonards Town
All which is humbly Submitted to the Consideration of the House
Signed p Order Richard Dorsey Q Com.

On page 252, Crackburns is mentioned again.

And Whereas the Land also lying at the Head of Britains Bay in Saint Marys County called Crackburns Purchase Containing One hundred Acres which he Conceived to be of much more Value than the other and is desirous the same may be settled to the same uses as the aforesaid Part of a Tract of Land…

These records tell us that this land was located at Leonard’s Town, today Leonardtown, at the head of Breton Bay, very close to, if not a part of, St. Clements.

Mary would have grown up here.

It’s possible that Mary and Bowling Speak lived at Crackborne’s Purchase, aka Leonard’s Town, after their marriage which probably occurred sometime between 1795 and 1798.

Mudd’s Rest

In 1708, Bowling and Mary purchased Mudd’s Rest from Barbara Mudd, a daughter of Thomas Mudd. Thomas’s first wife was Juliana Gardiner, daughter of Captain Richard Gardiner, who died in 1674. His second wife was Sarah Boarman. Bowling bought land in Boarman’s Manor and in Zachia Manor from Luke Gardiner, so these families were tightly intermingled. I’ve always wondered if Mary’s mother is a member of these early families but to be very clear, that’s pure speculation.

Unfortunately, early land and lease records are incomplete, and marriage records are nonexistent.

We know that Bowling and Mary had at least three children who were living when Bowling wrote his will in 1750.

Truth be told, they probably had several more children, assuming that they married about the time Mary was 20 years old, so roughly 1795. If she had her last child at age 43, and had one child every 18 months, she would have birthed approximately 15 children. If some babies died at birth, she may have had more.

While they were living in Leonard’s Town, they would have attended the original St. Francis Xavier Catholic Church established in 1661, located where the cemetery is today.

Clearly, Mary buried many children. At least some very likely rest here in tiny graves that are unmarked today, but would have been marked with small wooden crosses at the time.

After Bowling and Mary moved further north, their children were probably buried in the cemetery that became the Original St. Peter’s Cemetery on land owned by Bowling beginning in 1718.

St. Peter’s Church cemetery, then just known as the Upper Zachia chapel, was much closer to where they lived near Bryantown than St. Francis Xavier’s near Leonard’s Town.

It was 27 miles back to St. Xavier but only 6 to St. Peter’s which was then just a cabin surrounded by the cemetery that started with one burial beside the “church,” then grew. The “cabin,” perhaps someone’s home, would have been where services were held. Catholicism was illegal, so there were no official Catholic Churches, nor publicly-known services. Burials would probably have been small and quiet.

Based on the fact that Bowling and Mary purchased Mistake in 1718, where the old cemetery and the present-day church are located – Bowling and Mary’s land was the location where the early clandestine Catholic church was located. It’s also a possibility that the burials of their children were among the first in the early cemetery.

This is undoubtedly where Mary rests too, surrounded by her loved ones, buried on her son’s land.

Mudd’s Rest Location

Bowling and Mary were living in Mudd’s Rest after 1708. Where was Mudd’s Rest?

According to Mudd family researchers, they conclude that Thomas Mudd’s children were born in Port Tobacco, as was Bowling Speake, and that the land included in Mudd’s Rest was included with or near other land owned by Mudd at the southern end of Zachia Swamp, as can be seen here.

I circled this area on the map, above. You can see the southern portion of Zachia Swamp to the left.

This land driving north from Allen’s Fresh in the area where Mudd’s Rest was located is still a combination of forest, woodland, farmland, and modern-day homes. This road parallels and curves along Zachia Swamp to the west.

We don’t know when Bowling and Mary sold Mudd’s Rest, but in 1718, Bowling bought both “The Mistake,” land that would one day be inherited by his two sons, in addition to “Boarman’s Manor,” where he and Mary lived for the rest of their lives.

Boarman Manor

You can see Bowling’s Boarman land on the map above, with a closer view, below. The red pin marks the beginning of his land on Hunter’s Run.

In 1718, Bowling and Mary would have been about 44 years old. They would have had a young family – children from newborn or toddlers to maybe 20 or so. Their son, Thomas of Zachia, would have been 18 or 20 in 1718. Eventually, Thomas and his brother would inherit Mistake.

It looks like Bowling and Mary were trying to provide for their children by purchasing two tracts of land from the Gardiner family.

The Speake family was very closely allied with the Gardiners. I don’t know if that’s because of neighborly proximity, their Catholic faith coupled with the fact that the Gardiner family amassed in excess of 5000 acres of land, or if they were related through Mary’s unidentified mother.

We know almost nothing of Mary’s life on Boarman’s Manor.

Part of their land was tillable, part was forest, and part was swamp.

Archaeological excavations show that the early families interacted with the local Native people who may have lived in a village on their land.

Mary’s children would have grown up roaming the woods and learning to navigate the swamps.

The boys would have hunted and farmed, and the girls would have learned how to spin, weave, probably tend the garden, and of course, cook.

Life in Colonial Maryland

What was life like in Maryland just a few years after settlement in 1634 on St. Clement’s Island? According to the National Register of Historic Places registration for Port Tobacco:

According to contemporary descriptions, most of those lots maintained as private residences or inns and stores with living quarters above were usually fenced with paling or posts and rails for the better properties and wattle or brush fencing for others. Almost all of the lots included a small garden, a detached kitchen, a meat house and one or two smaller outbuildings. Lot sizes were a half-acre or less and a surprising number had as many as 7 or 8 buildings standing on them.

I would wager that this description of the homestead was probably similar for outlying plantations too. The more compact your buildings and homestead footprint, the more tillable land.

One building in Port Tobacco was 18X22 with a brick chimney.

One of the early homes in Port Tobacco known as Chimney House, for obvious reasons.

The largest and most opulent home was 46X34, or just over 1500 square feet. I wonder if inns were larger. Perhaps not, since men were expected to share beds with other male guests.

Within a generation, many of the original families had procured land further away. Port Tobacco was located on a swamp, stiflingly hot and humid in the summer. Waste disposal from both humans and animals was problematic due to the chronically low water table. Stagnant water is unhealthy in many ways.

It’s no wonder that when Bowling didn’t inherit his father’s land in Port Tobacco, he turned to farming. Bowling purchased Mudd’s Rest in 1708, then, described as a planter, bought Boarman’s Manor and Mistake at Zachia Manor in two separate transactions, 3-months apart, in 1718.

In 1743, when Bowling, again described as a planter, sold 250 acres of Mistake, Mary signed a release of dower.

Bowling’s 1750 Will

According to Bowling’s will, prepared in 1750, they had three living children. Bowling also remembered, by name, two grandchildren, although he and Mary unquestionably had several more:

  • Son Thomas (of Zachia) Speake to whom Bowling left part of Mistake where Thomas lived. Thomas was born about 1700 and married an unknown woman named Jane. They had 8 living children in 1755, including Edward, below.
  • Son William Speake to whom Bowling left part of Mistake with his dwelling place. William was born about 1716 and married Elizabeth Hagan, his sister’s husband’s cousin, and possibly a woman named Mary later in life. In 1779, he sold his portion of Mistake and was living in Frederick County, MD.
  • Granddaughter Ann Higdon to whom Bowling left “second choice of my beds an furniture my great chest one Dish & three plates one iron pot & Cattle and Sheep.” What we don’t know and can’t tell from this is which of Bowling’s children Ann Higdon was born to. We also don’t know what happened to Ann.
  • Daughter Mary Baggott to whom Bowling left cattle, sheep, one feather bed and furniture and one chest. Mary was born about 1710 and married John Baggott.
  • Grandson Edward Speake, son of Thomas Speak, to whom Bowling left “my Dwelling Plantation and also a small tract of land c(alled) the meadow also his first choice of the negroes and the first choice of my beds and fuz”

Men in colonial America didn’t write wills “just in case.” They wrote wills when they believed they were going to need them imminently. This tells us that Bowling was ill in 1750, and by inference, Mary was caring for him.

However, Bowling clearly recovered. In fact, so much so that in 1752, two years later, on March the first, he got himself in trouble.


Catholicism was outlawed in Maryland, and the Speake family was very clearly Catholic. We find Bowling in the court record in the Lower House of the Maryland judicial records:

The Lord Proprietary against Bowlen Speak} The said Bowlen Speak being bound by Recognizance for his Appearance here this Court, to answer of and concerning a Presentment by the Grand Jurors, for the Body of the Province of Maryland, against him found; for that he, on or about the first Day of March last, did, in a public Manner, drink the Pretenders Health, and good Success in his Proceedings; and being demanded whether he is guilty of the Premisses in the Presentment aforesaid mentioned, or not guilty, says he is guilty thereof, and submits to the Court’s Judgment thereon.

Bowling was fined 10 pounds of current money, but didn’t have it, so off to jail he went.


A historic survey of the Port Tobacco jail site identified CH-172, above, as the historic location.

The old jail was built in the 1860s on the location of an earlier jail, conveniently located behind the 1820s courthouse. In 1727, the county built a courthouse and jail on this 3-acre site adjacent Chandler’s Town that eventually became Port Tobacco.

In 1729, the county surveyor laid out the town. More than 100 lots were arranged along a grid of streets, lanes, and alleys, plus a marketplace. A number of already improved lots were incorporated, including one owned by Mary Speake, the widow of Bowling Speake’s brother, John. Mary, John’s widow, succeeded her husband as an innkeeper.

Although we don’t know exactly where the Speake Inn was located, we do know that John Speake, Bowling’s brother, was the most prosperous innkeeper in Portobacco. On May 12, 1717, for example, while establishing some specific property lines, the commissioners met at the “House of John Speake’s in Portobacco Towne” to inspect land records.

I can just see those men, in their colonial era attire of long-sleeved collared shirts, knee-breeches, long stockings, a waistcoat or vest, and black buckled shoes, wearing their powdered wigs, huddled around a table, with mugs of grog, of course, pouring over parchment papers.

Today, little remains of the original Portobacco Towne of more than 80 homes.

The red arrow points to the location of the jail, behind the courthouse.

I visited a few years ago, but I had no idea at the time that my ancestor was confined in that jail, even if it was for a relatively short time. I should have walked around back.

Today, only the courthouse and three historic homes remain of Port Tobacco.

The other homes lining the market square would probably have resembled these.

Today, the old brick courthouse functions as a museum.

The interior of the courthouse is restored in the style of a colonial courtroom. Bowling would have seen something like this, minus the contemporary people, of course.

Did Mary attend court with Bowling that fateful day? Was she watching? What about their children? Were they sitting with their mother? Women didn’t typically “attend court,” but maybe Mary did anyway.

Did Mary stare out the window at the jail with a sinking feeling as Bowling defiantly and perhaps a little too gleefully, with absolutely no remorse, pronounced that he was, indeed, guilty, and submitted to the court’s judgment thereon?

Did she know what was coming? She knew they didn’t have money to pay, and his fine wasn’t payable in tobacco. Actual coinage was required.

Was Mary frightened for her 72-year-old rather outspoken and unapologetic husband to be remanded to jail?

Were Catholics safe? What if he got into an argument? He clearly had no hesitation when it came to expressing his sentiments about what was, at that time, a highly controversial and political subject. Politics and religion, especially combined, are extremely volatile topics. A 72-year-old man wouldn’t be able to protect himself in jail.

Bowling’s friends pledged security that he would pay his fine and bailed him out, but apparently, the judge, obviously knowing Bowling, was not convinced that he would behave. His friends had to fork over 50 pounds to ensure his good behavior until the next court.

I’d wager that Mary, at home was MUCH harder on him than the judge. Maybe Bowling wished he were back in jail. Or maybe he went to Edward’s house, or Thomas’s, or William’s. Or maybe we went and cleaned the barn. At least until the next court when he had to show up with the money. How would Bowling have raised that money anyway?

Why did Bowling get into trouble?

The Pretender, of course, whose health Bowling was toasting, refers to Charles Edward Stuart, “Bonnie Prince Charlie,” grandson of the deposed King Charles – a Catholic. The 1745 attempt of father and son to reclaim the throne from the Protestant monarchy is known as the Jacobite Rebellion. In other words, Bowling was very publicly proclaiming that he supported overthrowing the British King. Not a good idea.

Given that Bowling’s exclamation was public, and he drank to the Pretender’s health, it’s fairly obvious that he visited the local pub and maybe had a mite too much to drink. So, not only did he probably come home drunk, in his 70s, he also managed to get himself arrested, prosecuted, fined, and jailed.

Yep, I bet Bowling was in one HEAP of trouble with Mary.

I can just hear his children now, “Mom, PLEASE keep him at home!!!!”


In 1754, Bowling and Mary must have been feeling their age, and they sold part of both Boarman’s Manor and Mistake.

On July 23, 1755, Bowling was still transacting business. He sold 121 acres of land in Mistake to his son, Thomas of Zachia. Ten days later, Thomas wrote his will.

What happened?

As difficult as those early years must have been for Mary, burying three or four times as many children as survived, plus Bowling’s 1752 “indiscretion,” which landed him in “gaol,” 1755 had to have been the worst.

On September 13, two wills were probated, one following the other, on the same day. Mary had lost both Bowling and her son, Thomas of Zachia, between July 23 and early September. For all we know, they could have died within days or even hours of each other.

I can’t even begin to image the grief Mary experienced. It’s hard enough to lose a spouse, but to lose an adult child at the same time would have compounded that immeasurably. Not to mention that Mary had grieving grandchildren as well. Who would take care of them? How would they all survive?

Did William, her surviving son, build the coffins for his father and brother both? Were other people sick too? Were they buried side by side at St. Peter’s?

We know that Mary was living in both 1750 and 1755, because she is named as the executor of Bowling’s will. He described Mary as “my well-beloved wife” and left her life estate in his “dwelling plantation” and the rest of his personal estate. After that, it was to belong to their grandson, Edward Speake.

This bequeath to Edward is quite interesting. Edward was born to Thomas of Zachia about 1727. By 1750, Edward would have been in his early 20s – strong and marriage age.

In 1750, Bowling and Mary would have been in their mid-70s, quite aged for that time and place. I don’t know of course, but I’d wager that Edward was living with Bowling and Mary, or at least on their property, helping them and farming the plantation. Perhaps this bequeath was Bowling’s way of guaranteeing that there was someone nearby to help. After all, his two sons were living up on Mistake, six or seven miles distant.

I’m sure the idea was that Mary would continue to live on their home property and Edward would farm it and take care of things for Mary.

After that, it would be his.

Apparently, Edward didn’t love the farm quite as much as Bowling did.

Mary’s Death

Mary died sometime after Bowling’s estate inventory was filed, although, unfortunately, not detailed, on February 12, 1756. She probably died before June 17, 1758, when Edward sold 17 acres known as Speake’s Meadow adjoining the upper tract of Boarman’s Manor to Philip Edelen for 2000 pounds of tobacco. However, that conveyance may not be an outright sale. The Speak/e/s Family of Southern Maryland book reports that part of the original deed is missing, but it appears that Edward may have mortgaged this land, not sold it outright. The 17 acres remained in Edward’s name until 1769, when it appears in Philip Edelen’s name, suggesting that Edward may have defaulted on the loan.

Not to complicate matters, but It’s possible that Edward was able to take a mortgage on that land even though Mary was still living, since he clearly had a right to it after her death. By 1758, Mary would have been about 83 years old.

Mary may have died before 1758, though, because Edward is shown on the rent rolls for 1756-1758 as owning the 17 acres of Speake’s Meadow. It’s hard to know whether they would have recorded Mary as holder of the life estate, or the person who was actually working the land, paying the taxes and who would be the eventual owner in fee simple.

In 1760, Edward sold the remaining 159 acres of Boarman’s Reserve to Samuel Hanson, complete with “houses, gardens, orchard, fences and other improvements” for another 2000 pounds of crop tobacco. Mary was unquestionably deceased by this time.

I wonder at the disparity of 17 acres for 2000 pounds of tobacco, and 150 acres plus the rest of the farm for the same amount.

Having stood on this land, much of it is woodland and swamp, so perhaps this 17 acres of meadow was quite valuable, comparatively speaking.

No Mitochondrial Lineage

I think the high colonial mortality rate in Maryland, plus the various types of “swamp sickness,” have come home to roost.

Mitochondrial DNA is passed from mothers to all of their children, but only passed on to the next generation by females.

To find Mary’s mitochondrial DNA, we either need to begin with her own female descendants or those of her mother or sisters.

  • Since we don’t know who Mary’s mother is, that avenue is not possible.
  • Mary Benson had no known sisters, so we’re striking out there too.
  • Mary Benson had one daughter, Mary Speake, her namesake who married John Baggott.
  • Mary Speake Baggott may have had more than two surviving children, but the only children we know of are John Bowling Baggott and Samuel Baggott, both living with their father and listed on the rent rolls after Mary’s death.

It’s possible that there are actually female lines, but we need to be able to identify and confirm them.

At this point in time, a Bible or maybe previously unknown letters or a family story is pretty much our only hope of identifying either Mary Benson’s mother, sisters (if she had any,) or additional children of her daughter, Mary Speake Baggot, assuming, of course, that she had more than two children who survived.

If you meet this criterion, please reach out. I have a DNA testing scholarship for you.

Mitochondrial DNA might well be the only remaining key we have available to unlock the identity of Mary Benson’s mother.


Follow DNAexplain on Facebook, here or follow me on Twitter, here.

Share the Love!

You’re always welcome to forward articles or links to friends and share on social media.

If you haven’t already subscribed (it’s free,) you can receive an email whenever I publish by clicking the “follow” button on the main blog page, here.

You Can Help Keep This Blog Free

I receive a small contribution when you click on some of the links to vendors in my articles. This does NOT increase the price you pay but helps me to keep the lights on and this informational blog free for everyone. Please click on the links in the articles or to the vendors below if you are purchasing products or DNA testing.

Thank you so much.

DNA Purchases and Free Uploads

Genealogy Products and Services

My Book

Genealogy Books

Genealogy Research

10 thoughts on “Mary Benson (c1675–c1758) Heiress of Crackbornes Purchase in Leonard’s Town – 52 Ancestors #383

    • Yes, Henson is a typo. You’re not confused, and thank you. How I did that and failed to catch it is beyond me, and not just once either.

  1. At the beginning of this blog you mention St. Clements Hundred,then move on. In case you are not already aware, St. Clement hundred has the only extant manorial records available. I found them at the FHL in SLC. I descend from Sir Thomas Gerard and that was his Manor. The records show some marriages and births, you have to search carefully to find them. Hope this might help.

  2. Thanks, Roberta, for pulling all this together. I’ve known the name of Mary Benson for quite a few years but knew nothing else about her! You continue to fill in the gaps!

  3. Richard Gardiner is my direct descendant
    – )
    1. Rebecca Winter (his sister)
    2. John Applegate (her son)
    3. Richard Applegate × (his son)
    4. John Applegate (his son)
    5. Martin Applegate (his son)
    6. Court Applegate (his son)
    7. Lydia Applegate (his daughter)
    8. Delbert Warman (her son)
    9. William Warman (his son)

  4. One of the wills mentions “first choice of the negroes”. Would there be more info in the slave records of these lands??

  5. Pingback: Hugh Benson (c1650-1687) and Wife, Catherine; Landowners in Leonard’s Town – 52 Ancestors #384 | DNAeXplained – Genetic Genealogy

Leave a Reply