The first American decade of John Prettiman I (1610–1688)

My tenth-great-grandfather John Prettiman (1610–1688) was an immigrant to the English colonies in the New World. While the connections between him and his American descendants are relatively solid and well-researched, the connection between him and his English birthparents has so far been impossible to definitively prove. I can only hope that some day a document might come to light that resolves this lack of certainty. Until then, as my cousin Pat Coonan stated in his 2005 work Minnesota Prettymans, 

…a process of elimination must be used to speculate on who the actual ancestor must be. Probabilities indicate that the John Prettiman that came to America is the son of Robert Prattyman and Dorothie Goddard.

I had originally intended this post to be a summary of all that we know of John Prettiman, but before too long I was astonished to discover all of the information that survives about John Prettiman after his arrival in Maryland. Accordingly, I’ll limit this post to just the events of John Prettiman’s first decade or so in the New World, from his arrival in Maryland in the mid 1630s to his departure for Virginia in 1643.

John Prettiman was most likely born in December 1609 to Robert Prettyman (1570–ca. 1626) and Dorothie Goddard (1587–?). If this is indeed true, then John Prettiman was christened on January 1, 1609/10 in Branston, Lincolnshire, England.

[su_box title=”A word about dual dates” box_color=”#79745d”]In this post and others about the 16th through 18th centuries, you’ll see me offer dates such as January 1, 1609/10. Why do I sometimes present two years instead of one? The answer is a long one and a fuller answer can be found here. In short, before 1582, Europe used the Julian calendar and marked the new year as beginning on March 25th. Pope Gregory XIII revised the calendar (to the Gregorian calendar) in 1582, but adoption of the Gregorian calendar was slow in Protestant countries such as England (which only accepted the Gregorian calendar in 1752). So for that period of 170 years, the days between January 1 and March 25 are now conventionally assigned two years—the first being the year in contemporary use, and the second being the year that we would now consider it to be.[/su_box]

Sailing to the New World

To the best of my knowledge, we have no record of when John Prettiman came to the new world, although the window for his immigration is narrowed to between 1634 and 1638 thanks to a couple of constraints:

  1. The first English colonists to arrive in Maryland came in two ships (the Ark and the Dove) that landed on St. Clement’s Island (in the Potomac River) on March 25, 1634.
  2. The first record of John Prettiman in the New World is a record in the Maryland Archives demonstrating that by February 21, 1638/39 he was living on a plantation in St. George’s Hundred, St. Mary’s County, Maryland (St. George’s Hundred is just 11 miles east of St. Clement’s Island). John signed his name to select David Wickliff as burgess for Hundred of Saint George.

John Prettyman (another descendant of John Prettiman) stated that “he may have come over in 1636 with Capt. George Evelyn, a relative.” I have so far not been able to find a record of the migration of Captain George Evelyn.

The British Isles in 1631, just before the emigration of John Prettiman

Whether John Prettiman sailed on the Ark or the Dove or another ship within the next five years, his journey would have probably been similar to that documented by Father Andrew White in his 1634 A Briefe Relation of the Voyage Unto Maryland. Nearly all voyages to the English colonies in the Americas in the 1630s followed this basic itinerary.

John would have made his way by land and by sea to Cowes on the Isle of Wight. In Cowes, he would have boarded a ship destined for Maryland. From Cowes, his ship would have sailed west through the Solent to Yarmouth. From Yarmouth, the ship would have sailed on to Cornwall where they could make their last stop in England before setting a course south towards Spain and Africa.

The ship would have sailed south along the coast of Spain and Portugal, catching the Canary Current to sail past Madeira and on to the Canary Islands. After taking on supplies and water in the Canary Islands, the ship would have continued south along the coast of west Africa and on to the Cape Verde Islands. If they stopped in the Cape Verde Islands, it would be their last stop before their voyage across the Atlantic Ocean. From Cape Verde, they’d be riding on the North Equatorial Current westward towards the New World.

John’s ship would have made landfall in the New World on the Island of Barbados. Their stop in Barbados would have been a longer-than-normal stop—perhaps a week or more—as the ship would have to restock provisions and the crew and passengers would have been eager to feel solid earth beneath their feet after weeks on the open ocean. After departing Barbados, the ship would have sailed north along the Leeward Islands of the Lesser Antilles, stopping at St. Christopher and St. Martin. From St. Martin, they would have sailed past the Virgin Islands, Turks and Caicos, and the Bahamas, and finally coming within sight of the coast of North America. From there, they would have caught the Gulf Stream and followed the coast north to the mouth of the Chesapeake Bay, then into the Chesapeake Bay to the Potomac River and finally to St. Mary’s City, then the capital of Maryland. The voyage would covered about 8,400 miles and would have taken about three months, of which seven and half weeks would have been spent at sea and the rest of the time docked at ports I’ve mentioned above.

John Prettiman in Maryland

The first written record of John Prettiman in America is from his Thursday, February 21, 1638/39 election of David Wickliff as Burgess for St. George’s Hundred. This document can be found on page 30 of volume 1 of Proceedings and Acts of the General Assembly January 1637/8-September 1664:

This single document is important in several ways. First, as mentioned above, it proves that John was in Maryland by early 1639. Second, John was able to sign his name, unlike almost half of the other signers of the document. This indicates that he was literate and educated. As Prettyman researcher D. Mitchell Jones states,

He could sign his name in an era when only small minority of men could sign their name. This is an indication that he had a background above that of the normal settler. It is an indication to me that his family, considering that he attempted to farm, was a landowning family in England with some education.

Third, the fact that he could elect a Burgess indicates that he was a freeman (i.e., a landowner). Maryland used a headright system, whereby colonists were given 50 acres of land for themselves and for each family member, indentured servant, slave, or other person that they brought over. While younger family members, indentured servants, and others could eventually buy their own land, the fact that he was a landowner less than four years after the founding of the colony indicates that John Prettiman was a freeman in Maryland, and not someone who came over as an indentured servant, slave, or younger family member.

On Thursday, July 30, 1640, John Prettiman was mentioned in a record of a recently surveyed parcel of land. His name was mentioned as being one of two people (along with WIlliam Brough) who recently cleared a neighboring parcel of land. This record was reproduced on page 373 of William Hand Browne and Louis Henry Dielman’s (1910) Land Notes, 1634–1655, in volume 5 of Maryland Historical Magazine:

The sixth Maryland General Assembly was held from Monday to Wednesday, March 21–23, 1641/42. John Prettyman was mentioned twice in the minutes of the General Assembly (I’ve highlighted his name on the images of the minutes below). These pages and thousands more were digitized and made accessible online by the Maryland State Archives:

Around March, 1641/42, John Prettiman was hired to travel aboard a pinnace on a two-month trading expedition to the Susquehannocks (more on this below in the section entitled “Violent Encounters with Native Americans”). Presumably around May or June, 1642, the Susquehannocks apparently attempted to destroy the pinnace and kill the men aboard it, but as the captain of the pinnace, Mathias de Sousa, testified in November 1642, John Prettiman saved the vessel and its crew:

… John Prettiman was out vpon the voyage 2 months (within 3. daies) & that by his meanes & presence he verily beleeveth the pinace & men were saved at that time from destruction by the sesquihanowes.

The full oath sworn by de Sousa is recorded on page 138 of William Hand Browne’s 1887 work, Judicial and Testamentary Business of the Provincial Court, 1637–1650:

On Friday, May 27, 1642, John Prettiman acknowledged that he was indebted to John Holes (Hollis) for one thousand pounds of tobacco, and he bound his crop of corn and tobacco for the debt. He signed and dated the acknowledgement and John Hollis registered this as deed on Saturday, October 1, 1642. This deed is recorded on page 117 of William Hand Browne’s 1887 work, Judicial and Testamentary Business of the Provincial Court, 1637–1650:

On Tuesday, August 2, 1642, John Prettiman was assessed a tax of 23 pounds of tobacco as a freeman in Saint Michael’s Hundred to help pay for the administrative costs of the Hundred. This document can be found on pages 145–146 of volume 1 of Proceedings and Acts of the General Assembly January 1637/8-September 1664:

On Thursday, August 4, 1642, Captain Thomas Cornwallis appeared in court to demand that John Prettiman pay him three hundred and sixty pounds of tobacco that Prettiman owed him, as well as one and a half pounds of beaver. This suit is recorded on pages 117–118 of Judicial and Testamentary Business of the Provincial Court, 1637–1650:

Later that same day (Thursday, August 4, 1642), Leonard Calvert (Cecil Calvert’s younger brother and the governor of Maryland) went to court to demand that John Prettiman pay three hundred and fifty pounds of tobacco for money Prettiman owed (presumably his tax bill) and damages for late payment. This suit is recorded on page 120 of Judicial and Testamentary Business of the Provincial Court, 1637–1650:

On Monday, August 22, 1642, the Lieutenant General declared that a General Assembly would be held on Monday, September 5, 1642, in the City of St. Mary’s:

Whereas I have appointed to hold a General Assembly at St Mary’s on Monday the 5th of September next to consult and advise of matters much importing the safety of the Colony at this present these are therefore to give public notice thereof to all persons whom it may concern and to require all freemen inhabiting within the Province to be at the said Assembly at the time and place aforesaid either by themselves or their deputies or delegates sufficiently authorized there to consult and advise touching the matters aforesaid whereof not to fail at their peril Given at St Mary’s this 22d August 1642

All freemen of the Province of Maryland were required to appear in person or by proxy unless they were out of the Province at the time of the meeting. John Prettiman’s name appears on a list of the freemen who were fined 20 pounds of tobacco for not attending the General Assembly. This document can be found on pages 172–173 of Bradley Tyler Johnson’s (1883) The Foundation of Maryland and the Origin of the Act Concerning Religion of April 21, 1649:

Violent Encounters with Native Americans

As previously mentioned, John Prettiman was hired to travel aboard a pinnace on a two-month trading expedition to the Susquehannocks, and his boat and men were attacked by the Susquehannocks, as documented by the oath of the captain of the pinnace, Mathias de Sousa:

about March was twelvemonth he was appointed by mr Pulton to goe in his pinace as skipper & trader to the Sesquihanoughs & by him appointed to hire men at Kent [Island] for the voyage, & that he would write to mr brent to assist him in it & that at his coming to Kent with the knowledge & consent of mr brent he hired John Prettiman to goe vpon the voyage, & that he hired him for 200 tob. p month, and that accordingly John Prettiman was out vpon the voyage 2 months (within 3. daies) & that by his meanes & presence he verily beleeveth the pinace & men were saved at that time from destruction by the sesquihanowes.

This attack was just one of many suffered by the colonists of Maryland in the summer and fall of 1642.

On Tuesday, September 13, 1642, Leonard Calvert, the Governor of the Province of Maryland, issued a proclamation of war against three local Native American tribes.

To see how they got to this point, I need to provide a bit of background to the situation. As you’ll see, colonists had been clashing with other colonists, Native Americans had been clashing with other Native Americans, and finally, colonists and Native Americans began clashing with each other as a result of these earlier clashes.

The Province of Maryland was intended by George Calvert to be a haven of religious tolerance for English Catholics. George died before being able to see his haven of religious tolerance become reality, but his son, Cecil Calvert, fulfilled his father’s dream. The first colonists to settle Maryland under Calvert’s charter landed at St. Clement’s Island and then built their first settlement at St. Mary’s City. They were not the first English to settle on the Potomac River, however.

William Claiborne, a resident of the Virginia Colony settlement of Jamestown also a Catholic, had returned to England and been granted the right to trade with Native Americans on all lands in the mid-Atlantic where there was not already a patent (charter or grant of land) in effect. Claiborne sailed from England on May 28, 1631, with a group of indentured servants, and landed on Kent Island in the Chesapeake Bay later that year to establish a Virginia Colony settlement and trading outpost.

Calvert’s Maryland charter was huge, however, and included land on either side of the Chesapeake Bay from the Virginia colony in the south to the 40th parallel (just north of colonial Philadelphia). Kent Island was clearly included in Calvert’s charter, but Claiborne refused to acknowledge this, instead insisting that Kent Island was part of the Virginia Colony.

The newly founded Maryland had until very recently been controlled by the Algonquian peoples, including the Powhatan. Disease and warfare over the first couple of decades of European contact had markedly reduced the populations of the Algonquian speakers, making them vulnerable to encroachment by other Native American groups. One such encroaching group was the Susquehannocks, who were fleeing south to avoid Iroquois aggression. By the time that the Kent Island trading outpost was established, the area was inhabited by the Susquehannocks.

William Claiborne had established peaceful and mutually beneficial relations with the Susquehannocks, so when the Maryland colony tried to remove Claiborne from Kent Island by force, that action had unexpectedly large consequences. According to Michael Oberg’s (2003) Dominion and Civility: English Imperialism and Native America, 1585–1685 (page 195),

When the Marylanders decided to drive William Claiborne from his Kent Island post, the proprietary government gained not only his enmity, but that of the Susquehannocks as well. After attacking Maryland’s fur-trading allies, the Piscataways, at two villages along the Potomac and sacking Jesuit storehouses along the Patuxent in the summer of 1642, the Susquehannocks killed a number of settlers near St. Mary’s City. That September, Maryland declared war against “the Sesquihanowes, Wicomeses, and Natacoque Indians,” all considered “enemies of this Province” and therefore to be “proceeded against by all persons.” In the summer of 1643 Maryland launched two attacks. The first of these ended inconclusively, as the Susquehannocks avoided English firepower, and in the second the Susquehannocks routed the Marylanders, capturing fifteen prisoners whom they promptly tortured to death.

Oberg mentions only the two larger-scale attacks in the summer of 1643, but there were several smaller skirmishes and expeditions against the Native Americans between the fall of 1642 and the summer of 1643. In addition to the attack of his trading pinnace mentioned earlier, John Prettiman was involved in at least one more of these earlier encounters.

The following record, taken from the Proceedings of the Council of Maryland, pages 119–120, shows that John Prettiman participated in a three-week expedition against the Susquehannocks between September 21 and October 13, 1642, as his name was on the list of people to be paid for their services during this expedition. This expedition appears to have included only 18 men along with 20 prisoners or slaves (the 20 persons pressed by Sheriff Edward Parker):

On Friday, November 4, 1642, John Prettiman appeared in court to demand that Thomas Coply pay him three hundred pounds of tobacco that Coply owed him for wages and for tobacco purchased by Copay. This suit is recorded on page 139 of Judicial and Testamentary Business of the Provincial Court, 1637–1650:

On Friday November 25, 1642, John Prettiman was named in a suit brought by Cutbert Ffennick. Cutbert Ffennick asked the court to grant him a judgement against John Prettiman for six hundred pounds of tobacco to compensate Ffennick for John Prettiman trespassing and killing a steer calf that belonged to Ffennick. This suit is recorded on page 152 of Judicial and Testamentary Business of the Provincial Court, 1637–1650:

On Friday, December 2, 1642, John Prettiman appeared in court to participate in a lawsuit, but the hearing was postponed for a week when the plaintiffs did not appear in court. This suit is recorded on page 158 of Judicial and Testamentary Business of the Provincial Court, 1637–1650:

On that same day (Friday, December 2, 1642), John Prettiman appeared to take part in a complaint of trespass against him by Cutbert Ffennick. As with the other suit earlier in the day, it was postponed for a week due to Ffennick’s absence. This complaint is recorded on page 158 of Judicial and Testamentary Business of the Provincial Court, 1637–1650:

On Monday, December 5, 1642, court papers note that a case between Cutbert Ffennick and John Prettiman should be suspended until February 1, 1642/43. This decision is recorded on page 161 of Judicial and Testamentary Business of the Provincial Court, 1637–1650:

On that same day (Monday, December 5, 1642), John Prettiman was the subject of a court action. William Broughe asked that the earnings of John Prettyman be bound to ensure that Prettiman paid Broughe the amount of the settlement. Broughe’s request was granted. This request is recorded on page 162 of Judicial and Testamentary Business of the Provincial Court, 1637–1650:

On Monday, January 2, 1642/43, John Ormsby and John Prettiman sued John Thompson, arguing that Thompson owed them one thousand pounds of tobacco. Ormsby and Prettiman won their suit on February 1, 1642/43, and John Prettiman transferred his interest to John Ormsby. This suit is recorded on pages 165–166 of Judicial and Testamentary Business of the Provincial Court, 1637–1650:

On Monday, January 16, 1642/43, John Prettiman was named in a suit brought by the widow Jane Cockshott. Jane Cockshott demanded that a man named Thomas pay her 420 pounds of tobacco owed for goods she provided to Thomas and John Prettiman. This suit is recorded on page 172 of Judicial and Testamentary Business of the Provincial Court, 1637–1650:

On Sunday(?), May 14, 1643, John Hollis appeared in court to demand that John Prettiman pay him the five hundred pounds of tobacco that Prettiman owed him. This suit is recorded on page 204 of Judicial and Testamentary Business of the Provincial Court, 1637–1650:

After this date (May 14, 1643), there is no further record of John Prettiman in the Maryland court archives.

John Prettiman departs Maryland for Virginia

At some point in the summer of 1643 (between May 14, 1643, and August 31, 1643), John Prettiman departed Maryland for the Eastern Shore of Virginia. I have not yet been able to track down the source of the following deposition, but Prettyman researcher D. Mitchell Jones stated that John Prettiman was mentioned in the deposition of John Williams in the Accomack-Northampton Court on August 31, 1643:

This deponent saith That hee and his Company being resolved to Remayne att St. Maryes went out to stand for a Deere and comeing back Rowland Vaughan spooke unto John Prettyman to goe with this deponent and his Company to the Sweades by Land whereunto the said Prettyman Answeared saying I am ingaged I cannot goe Whereupon Rowland Vaughan voluntaryly proferred to give the said Prettyman a bill of Nyne hundred pounds of tobacco to saitsfy his debts if hee would goe along with him and his company whereupon this deponent and all his Company proferred the said Rowland saying it shall not bee given wee will all make you satisfactin att the Dutch Plantation with which proferr the said vaughan was content.

In subsequent posts on John Prettiman, I’ll cover John’s life in Virginia, as well as what we know about John’s English birth family.

If you can contribute any information about John Prettiman’s stay in Maryland, please let me know in the comments section below.

3 thoughts on “The first American decade of John Prettiman I (1610–1688)

  1. Hello; I am looking for any information to construct the family tree of the Prettyman’s in Virginia in the 1600’s and 1700’s. I recently noticed that a street in Urbanna, Virginia (river port town in Middlesex County, VA) was named “Prettymans Rolling Road”. This name refers to the rolling of hogsheads (6 yo 8 feet diameter barrels of tobacco) down to the port of the river to be loaded for shipment to Europe. A year or so back I had found a possible Miller relative named Robert Miller in Elizabeth City County, Virginia. In Robert’s 1692/1693 will notes his estate to be divided between his wife “Ephica” Miller and “Ephica” and Thomasin Prettyman. Witnessed: William Marshall and John Phells(sp?). Inventory signed by “Aphia” Miller. It is possible “Aphia” was read as “Ephica” on some lines of the old will in the transcription.

    I am trying to determine the relationship of Thomasin Prettyman to the few Prettyman’s in Middlesex Co., VA. This may tied my known Miller family in Middlesex Co., VA (starting with Patrick Miller b- 1620 in Scotland; arrived in Virginia around 1650) to the Robert Miller in Elizabeth City Co., VA. There are indications that my Miller’s were involved with the Virginia tobacco trade back to Glasgow, Scotland in the 1600’s up to the the 1670’s when this trade virtually ended leading up to the American Revolution.

    Thank you for your time,

    Jim Miller
    Chapel Hill, North Carolina

  2. Hi Jim,

    I’m sorry it’s taken so long to respond. I was away on a long vacation when you wrote and I’m just getting my genealogy legs back.

    I don’t know that I’ve got too much more to help you with at the moment, but I hope that’ll change in the next couple of years. I’ve only recently started to dig into my distant Prettyman roots, and this post on John Prettyman I was my first foray into that branch.

    I’m hoping to pick up my work on the early Prettymans later this year after my current research lines are wrapped up.

    Could you tell me more about Thomasin Prettyman? Anything you’ve got would help. I don’t yet have a Thomasin Prettyman in my tree, but it’s become a bit of an obsession for me to try to tie in American Prettymans to my line, and I’ve not yet found one American Prettyman who isn’t descended from John Prettyman I. Let’s start there and get her connected to my tree. Please also give me info on at least one of the Middlesex County Prettymans to see if I can tie them into my line as well.

    Once I get this info from you I’ll let you know what I find.

    All the best,


    • Michael,

      Thank you for your reply. Thomasin Prettyman AKA Prittiman was born 10/3/1687 in York County, Virginia (Charles Parish Register). He was the son of Thomas Prittiman (b- Abt. 1665) and a woman named Aphia AKA “Ephica” in a later will transcription of her 2nd husband Robert Miller (b- Abt. 1672 location unknown; D- 1/25/1693 in Elizabeth City County, VA (Back River)). Aphia’s maiden name is unknown. Charles Parish in York Co., VA is only 5 to 10 miles from the Back River area of Elizabeth City Co., VA.

      Thomasin (assume may have also been called Thomas) had one other known sibling; a sister named Aphia Prettyman.

      Thomas Prittiman likely died about 1690 and his wife Aphia then married Robert Miller. Robert Miller’s 1693 will in Elizabeth City Co., VA notes “Ephica” and Thomasin Prettyman (the children his wife and her 1st husband Thomas Prittiman had together). An Aphia Miller is noted as doing Robert Miller’s estate inventory in the will transcription so it is though “Ephica” and Aphia were different reads of the same name during the transcription of the will hundreds of years later. Likely the child Aphia was named after her mother also Aphia. Aphia Miller AKA Prettyman then married a 3rd husband, Francis Rogers on 10/15/1698 in Elizabeth City Co., VA.

      I assume that Thomas Prittiman who died about 1690 descends from John Prettiman (1610-1688) of Maryland. My Miller’s in Virginia also had other ties to people in Maryland; however the names in the documents you posted on this website do not strike any bells with me. I would be interested if you could find the tie between Thomas and John Prettiman in your future research.

      Jim Miller

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