20 Unusual Tales From Colonial America That Aren’t In History Books

When the Mayflower set sail from Plymouth on a September Saturday in 1620, there were 102 passengers on board. One of them was John Billington, and he was accompanied by his wife Eleanor and their two boys, John and Francis. The four of them were some of those who survived their first winter in the New World. Forty-five other Pilgrims did not.

Billington was apparently a troublesome man, often coming into conflict with the settlement’s authorities and his neighbors. Things came to a head in 1630 when Billington shot and killed fellow Pilgrim John Newcomen. Billington was duly charged, tried, and found guilty. The sentence was death by hanging. This gave Billington the unenviable distinction of being the first of the colonists to be judicially executed. 

Born into poverty near Boston, Massachusetts, in 1748, Timothy Dexter had big ideas about his future, which seem to have centered for the most part on becoming extremely wealthy. Clearly a man with a ravenous appetite for risk, his first financial coup was the result of a seemingly insane currency gamble.

During the Revolutionary War, the 13 colonies had issued their own currency, the Continental. But the money quickly became devalued by inflation. After the war, these dollar notes had no apparent value. But Dexter thought otherwise and bought up as many as he could, paying rock-bottom prices. Eventually, the U.S. Government agreed to buy up all Continentals at 1 percent of their face value. Dexter had paid much less than that, so overnight he became fabulously wealthy.

One of the strange consequences of the ruthless persecution of Jews during the 16th-century Portuguese Inquisition was that many of them pretended to be Christians. That was understandable — and certainly preferable to torture or a cruel death. The Jews who took to Christianity, at least nominally, were called Conversos. Judah Monis was born a Converso, but as an adult he gravitated to his ancestral Judaism.

Monis emigrated to America, arriving in New York City in 1715 before moving to Cambridge, Massachusetts, some five years later. That turned out to be a good idea since the city was home to Harvard College. Back then students there had to learn Hebrew, but people knowledgeable in the language were few and far between in Cambridge. So Monis got a post at Harvard as a Hebrew teacher. But Harvard did not employ Jews, so he had to convert to Christianity. Again. 

The good folks of the South Carolina colony got the shock of their lives one September day in 1739: their African slaves had risen against them. About 20 of them, under the leadership of an Angolan known only as Jemmy, held a rebellious meeting by the River Stono in St. Paul’s Parish. The slaves raided a gun shop, arming themselves with weapons and ammunition. 

The Africans then marched south, pausing to kill some of the slave masters. As they progressed, the rebel numbers swelled to roughly 50. The white death toll may have been as high as 25. But once the colonists had organized themselves, the fate of the rebel slaves was sealed. A gun battle resulted in some 30 African deaths. A number, perhaps another 30, escaped. But all were eventually tracked down and killed.

Born in 1711 on Monamoy, an island of Cape Cod, Patience Boston seems to have been a bit of a handful, to put it mildly. Puritan innocence hardly comes into it. To be fair, her start in life was far from easy, with her mother dying while Patience was only three. When she was 12, she made three — happily unsuccessful — bids to burn her own house. But as she entered her teens, things didn’t improve.

One source describes how she “went out at Nights, and kept bad Company, and followed lewd Practices.” She married and had a baby which quickly died, perhaps because of her drunken excesses. A second child died within two months. Later, Boston became the servant of a man in Maine. Her depravity reached new depths when she murdered her master’s grandchild by shoving him into a well where he drowned. Found guilty of murder, Boston was executed in 1735.

In 1763, Chief Pontiac of the Ottawa people led a rebellion against the British colonialists. He had created a formidable coalition of forces which included Huron, Potawatomis, Shawnee, and many other tribes. The rebels attacked various targets in Ohio Country and western Pennsylvania. One major engagement came at Fort Pitt in western Pennsylvania, where Pontiac’s warriors besieged the garrison.

During the siege, smallpox broke out in the garrison’s overcrowded conditions. And when some of the Native Americans came to the fort for a parlay, the British had a bright idea. The diary of a trader at the fort, one William Trent, explained the plan. “Out of our regard for them, we gave them two Blankets and an Handkerchief out of the Small Pox Hospital,” Trent wrote. “I hope it will have the desired effect.” The cynicism is breathtaking.

Alexander White’s story is a salutary reminder that as well as hardworking and aspirational types, immigrants from Europe were sometimes dastardly criminals. White sailed from County Tyrone on Ireland’s west coast sometime in the mid-18th century. After arriving in Boston, he found himself a position as a seaman, working as a mate aboard a cutter.

White hatched a plot to rob the captain of his ship while it was moored in Great Cow Harbor on the north shore of Long Island, New York. But White’s plan quickly went awry as he tried to overpower his captain, and his unfortunate victim was killed in the struggle. Meanwhile, another man aboard the ship dived into the sea to escape the murderous mate — and went straight to the authorities. White was quickly arrested and tried for murder. Found guilty, his sentence was hanging.

Few people have not heard of the Salem witch hunts and trials of 1692 and 1693. But much less well-known are the similar purges carried out in Connecticut nearly 50 years earlier. In 1646, a servant called Mary Johnson was accused of witchcraft. After intense interrogation including torture, she eventually confessed. Following a stay of sentence to allow her to give birth, Mary was hanged for her alleged sorcery.

Then there was Alse Young of Windsor, Connecticut. Information about her is scant and contradictory — even her given name is uncertain. It may have been Achsah or Alice. But we do know she was accused of witchcraft and hanged for her offense in 1647. All told, up until the late 1660s, 16 accused of sorcery in Connecticut were executed: the vast majority were women.

Okay, pretty much everybody knows that the Mason-Dixon Line divides the southern states of the continental U.S. from the northern ones. But, although intriguing, the story of how the line got its name is rather less well-known. In fact, the title derives from a long-running and acrimonious dispute between neighbors back in colonial times.

Those argumentative neighbors were the folks of Pennsylvania and the residents of Maryland. The antagonists fought each other for some eight years in bitter skirmishes, collectively known as the Conjocular War or Cresap’s War. They battled over where the border between the two territories lay, and in particular who could lay claim to the city of Philadelphia. Eventually, in 1767, two surveyors settled the dispute once and for all. Their names? Charles Mason and Jeremiah Dixon.

It’s 1697, and Hannah Duston is at home in Haverhill, Massachusetts, with her newborn baby and her neighbor, Mary Neff. Native Americans, probably Abenaki, attack the township. They capture the two women and the baby and some other townsfolk, spiriting them away. As the party travel away from Haverhill, the warriors brutally kill Hannah’s week-old baby girl.

After a journey of a couple of weeks, the warriors entrusted Neff and Duston to a Native American family. They joined another abductee, 14-year-old Samuel Leonardson. One night, while the Native American family were asleep, Duston, Neff, and Leonardson attacked and killed four of the adults and six children. They escaped in a canoe, paddling along the Merrimack River to Massachusetts. For her ruthless act of revenge, Duston became a hero to the colonialists.

Most of us probably picture the early English immigrants to America as driven by the desire to escape either poverty or religious persecution, and perhaps both. But by no means had all of the thousands who landed on the shores of America been willing travelers. Some had no choice but to make the perilous journey across the Atlantic from Europe.

From as early as 1615, English courts started to send convicted felons to the American colonies. And over the course of 75 years, as many as 52,200 criminals were shipped off, with 20,000 of those winding up in Virginia. The colonists could buy these convicts — they cost less than indentured workers or African slaves. And then there were the children. Orphans and impoverished youngsters were also shipped off to America and into servitude. 

The dreadful history of African slavery in colonial America and after the revolution is well known. Much less familiar is the tale of Native American slavery — yet it was a practice which started not long after the first colonists reached New England and began to build settlements. The first records of First Nation slavery date from as early as 1636. 

Many Native Americans were captured and enslaved during King Philip’s War. That was a rebellion by indigenous people against the settlers in 1675 that lasted into the next year, when it was crushed. People seized and taken into slavery during the conflict were transported as far afield as north Africa, Spain, and Barbados. By circa 1700, more than 1,200 Native Americans had been enslaved.

Born in about 1730 in London, England, William Beadle found himself living in Fairfield, Connecticut by 1773. Life there seems to have been good: he was a prosperous merchant and could count himself as a member of Fairfield’s wealthy elite. And he was married to Lydia, an apparently happy union which had produced three daughters and a son. But there was trouble on the horizon.

Beadle’s affluent life was upset by the British reaction to the Boston Tea Party. Parliament in London had decreed that the port of Boston should be blockaded, and Beadle was one of the patriotic merchants who continued to supply the city. So he accepted the revolutionary money, Continentals, in payment. But the currency quickly became so devalued it was worthless, leaving the trader ruined. His mind seemingly unbalanced by his financial downfall, he murdered his wife and children before taking his own life.

Led by Chief Opechancanough, the Powhatan people rose against the British colonists of Jamestown in 1622. Attacking the township and surrounding district, the Native Americans destroyed property and killed some 350 settlers. Colonial reinforcements soon arrived and began to take punitive action against the Powhatan. The harsh British retaliations hit the rebels hard.

Chief Opechancanough decided it was time to open talks. The leader and his people entered a peace agreement with the colonists, who were represented by Dr. John Potts and Captain William Tucker. To celebrate the peace, and as an apparent gesture of goodwill, Tucker and Dr. Potts gave the Powhatans a supply of wine. But they’d added poison to the beverage, and 200 of the Native Americans died as a result.

Cockacoeske became leader of the Pamunkey people in New England in 1656 when her husband Chief Totopotomoy died. Her tribe was one of those that belonged to the wider Powhatan people. She had an illustrious ancestor in Chief Opechancanough, who had led the Powhatan in violent resistance to the British settlers earlier in the 17th century. 

By 1677, things were very different than they had been in the days of Opechancanough. Cockacoeske foreswore armed resistance and instead negotiated a peace with the colonial authorities after the Pamunkey had been attacked by settlers. She even offered the services of her warriors to help in the defense of settler lives and property from the attacks of other Native American tribes.

Once the colonists of Jamestown had established their township early in the 1600s, they had time to take stock. They realized there was a serious problem: almost all of them were men. For obvious reasons, that could've had a dire impact on the future of the colony. No females, no babies. They needed women, and they needed them badly. 

So in 1620, the men of Jamestown decided to do something about the acute shortage of females. Realizing they needed to provide incentives to persuade single women to leave Britain for Jamestown, the Virginia Company came up with a package. The firm would pay for the journey to the New World, as well as providing clothing and even a plot of land. Some 146 women answered the call and the future of Jamestown was assured. 

We have a British admiral, Sir William Penn, and his son, also William, to thank for the creation of colonial Pennsylvania. In 1660, after the interruption of the Cromwell years, the British monarchy had been restored with the coronation of Charles II. Sir William then spent a considerable amount of his own money in refurbishing the Royal Navy.

Sir William’s expenditure was supposed to be a loan to the Crown. But 20 years later, with Sir William already in his grave, the debt had never been repaid. So William junior approached Charles with a plan. Instead of a cash repayment, Penn would take possession of a large tract of land west of the Delaware River to establish a colony. Apparently, Penn was minded to call the territory either Sylvania or New Wales. But Charles preferred the name Pennsylvania. As we know, the King got his way.

We don’t know much about an African man called John Casor, but what we do know is highly significant. Back in the mid-17th century, Casor was an indentured laborer in Virginia. That was in many ways a position akin to slavery, but there was a crucial difference. An indentured worker had a contract with a master, and after a set number of years of compulsory labor, he automatically became free. 

A key point about the indenture system was that it didn’t matter what race you were. Once you’d worked your time, you were free. But Casor had a dispute with his master Anthony Johnson about the status of his indenture. When the case came to court in 1654 or 1655, the decision was devastating for Casor: he was declared to be a slave for life. For the first time, slavery for Africans was a legally recognized institution.

Founded in 1607 at the behest of King James I, the early years of Jamestown in Virginia were marked by hardship, disease, and hunger. The colonists tried various enterprises to create the wealth they needed to survive. They tried forestry, silk-making, and glass manufacture, with a notable lack of success. But a new opportunity came along, one that would establish the prosperity the colonists craved.

It was in 1610 that 150 new settlers arrived in Jamestown. One, John Rolfe, smuggled in something with him: tobacco seeds from South America. Rolfe planted his illicit seeds and eventually tobacco became a lucrative cash crop for Jamestown, transforming it into an economically viable settlement. There was a paradox in this, however, as Jamestown’s royal patron, James I, had a deep-seated hatred of the evil weed in all its forms.

The settlers who landed on America’s east coast in 1607 and established Jamestown in Virginia are often thought of as the first colonists from England. But in fact they were preceded 20 years earlier by a group that had arrived on Roanoke Island just off the coast of modern North Carolina in 1587. Yet there’s a good reason why Roanoke is much less well known — and it’s thoroughly intriguing.

The truth is that the colonists of Roanoke — 118 men, women, and children — simply disappeared off the face of the Earth. When a party reached the island in 1590, all that they found to indicate where the settlers had gone was the word “Croatoan” carved into a timber post. There was an island called Croatoan, now Hatteras, 50 miles from Roanoke. Did they go there? The mystery has never been solved.