Edmund Scarborough & Ann Toft

by Dana Kester-McCabe

This is the story about colonial Delmarva’s power couple Edmund Scarborough and Ann Toft.

Colonel Edmund Scarborough is a well-known character in the history of colonial Delmarva. For some he is considered a rapscallion robber baron who displayed the rugged individualism we Americans so admire. To others he was a bigot who fomented discord between local Indian tribes and other settlers all for his own personal gain which was considerable. He and his mistress were one of the New World’s most notorious power couples.

Edmund Scarborough was born in 1617 and left merry old England with his parents for the Virginia colony when he was just three years old leaving behind a brother Charles who was in medical school. The father, Edmund Sr. was a land owner, attorney, and a justice of the peace. When he died, the younger Edmund took over as the head of the family’s colonial estate and began a quick rise in local government and commerce. He and his wife Mary had several children and a large plantation near what is now Onancock. He traded in cattle and tobacco. But he really made his money in headrights.

A ‘headright’ was the colonial custom of exchanging land for the paid passage of indentured servants from the old country to do the labor needed in the new world settlements. The British government made these deals to relieve their over-population problem and further strengthen their claim on territories in the New World. Edmund made a fortune at this. The more headrights he bought the more land he was given. This he either traded or used to make money in other ways. Besides farming he had a salt works, and a shoemaking operation employing nine cobblers at one point. He also bought a fleet of ships which he used to trade goods in New England and the Caribbean.

Edmund was a busy guy. He was a colonel in the local militia. He was the high sheriff and a justice of the peace. He was a burgess or mayor who served as the speaker of the Virginia House of Burgesses. At one point, he was the surveyor general of the colony.

One of the reasons we know so much about Edmund is that he was in court all the time. This was partly because that was where all legitimate business was conducted and recorded. He also sat on a panel of judges to settle all kinds of cases from civil matters to misdemeanor conflicts to criminal acts. Edmund also found himself in court frequently because, for all the wealth he was amassing, he had a bad habit of skipping out on his debts.

In 1644 Ann Toft was 21 when she was first mentioned in the court records of Virginia’s Eastern Shore. This was when Edmund first made a gift of land and headrights to her and the transfers were legally recorded. There is no record of where she came from. She seems to have appeared in the region several years earlier. Some records called her Mrs. Toft, but there is no official paperwork indicating who Mr. Toft was or if he even existed. We do know that Ann was quite beautiful and that she had three daughters: Annabelle, Attalanta, and Arcadia. Many historians surmise that these were actually Edmund’s children. He is said to have built Ann a lavish plantation. This was called Gargaphia after a place in Ovid’s Metamorphosis where the goddess Diana would have romantic encounters. The only remnant of this colonial mansion is a derivative of the name which was given to the town Gargatha, Virginia, and nearby Gargathy Bay.

Edmund’s wife Mary was recorded on several deeds of transfer to Ann for land she owned with Edmund at this time. One of those was that deed giving Ann ownership of Gargaphia. It also gave Edmund the right to inhabit the plantation as long as he lived. Either Mary did not know what she was signing or she did not have the power to object to these dealings with her husband’s mistress. Meanwhile Ann learned a lot from Edmund. He taught her to trade in headrights and real estate. She became a successful merchant in her own right.

He probably could have learned a thing or two from her. She quietly took care of her own affairs and generally avoided trouble which Edmund apparently could not resist. People were regularly suing him for some debt or another. He often would simply ignore court rulings that went against him. After one of his ships was confiscated during the war between the English and the Dutch he tried to seize Dutch ships in retaliation. He had a long running feud over property lines with his neighbor Obedience Robbins. Edmund eventually won that case when he got the government to divide the Eastern Shore of Virginia into the two counties we now know as Northampton and Accomack.

Early on Edmund had reasonably good relations with the Indian tribes in the region, buying some land from them. But, eventually he began to loath them and he engaged in a series of campaigns against them. At one point, he invited leaders of the Pocomoke tribe to a feast and while they were eating his men began shooting over their heads creating a riot during which some of the native guests died. He denied any fault and because of his position in the local community he got away with it.

There was only one other group he hated more than those Indian tribes. That was the Quakers settlers who had bought land near him. Now most accounts of these contentious relationships suggest that these were just part of a scheme he had to take over the lower Eastern Shore of Maryland for Virginia. He presented his justification for his actions as a staunch member of the Church of England. He attacked Quakers and Puritans for their beliefs and tried to run them out of the county. In 1663 he used all this strife to get an appointment to negotiate a settlement with Maryland’s government to establish the northern line of Virginia’s Eastern Shore which has stood ever since.

Edmund continued to harass any neighbors he did not like. He also traded weapons with some of the Indians to make them look dangerous and then tried to turn them against the Quakers who were known for their honesty and peacefulness. Technically this was an act of treason. All this led his now fed up neighbors, to appeal to authorities to do something about him. A warrant was sworn out for his arrest. But, remember that brother Charles left back in England studying medicine? Well he had risen to the position of a knighted court physician serving as the personal doctor to King Charles II himself. He used his influence to fix things for his little brother. Edmund got off scot-free and this gave him the impunity to continue harassing his Quaker neighbors until they finally moved across the line into Maryland.

Meanwhile Edmund’s personal life was also very messy. He accused his church parson of having an affair with his wife Mary. The motive behind this is unknown. Apparently, the hypocrisy of it was lost on Edmund. The parson sued for slander forcing Edmund to retract his statements.

Then one night when Edmund was staying with mistress Ann at Gargaphia, a laborer had an argument with him which devolved into a brawl. The men found themselves appearing in court having to explain the melee. A few months later Edmund was called into court again to answer for his continued attacks on the local Indians. This time the court stripped him of all his official positions both civil and military for putting the community in danger of an Indian attack. This must have finally knocked the wind out of his sails. Less than a year later he died of small pox at the age of 54.

Two months after he was gone Edmund’s mistress Ann married Captain Daniel Jenifer. In 1672 she sold 4,000 acres of land she owned in Jamaica supposedly in order to pay Edmund’s estate for some debt she owed him. Perhaps his widow Mary finally stood up for herself and demanded some compensation for her husband’s infidelity. At that time, Ann and Captain Jenifer were probably the wealthiest land owners in the region. Their holdings included 4,700 acres from present day Gargathy Bay all the way to the Maryland line. They had one son together. When her daughters came of age she gave them each a generous gift of land, livestock, and household goods. Records show that they had lived up to a bargain with their mother and step father to remain unmarried until they were seventeen and to choose respectable husbands.

There are few records of Ann Toft after that. This may seem mysterious but it is likely that she simply gave over her affairs to her new husband and lived out her days quietly out of public view. All that remains now are the legends of a colonial beauty and the beastly behavior of her paramour.


Descendants of Edmund Scarborough
from Cynthia McDaniel, Ghote - Updated January 13, 2004

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