Popular culture often portrays the holiday season as a time of joy, goodwill, and festivities. However, the harsh reality is that crime and mischief have always been a part of Christmas in Delaware, with incidents ranging from political power plays and unruly schoolboys’ antics to racially tinged acts of theft. Let’s explore three notable such events that span three centuries of Delaware’s Christmas history.
In the 17th century, political tensions between Maryland and the residents of what later became Delaware led to the notorious Christmas Eve Whorekill raids. The British crown had granted the peninsula to the Calverts of Maryland in 1632, but the Swedes, and soon after the Dutch, ignored this claim, establishing settlements in Whorekill (this name derived from the Dutch “Hoeren-kil,” translating to “Whore’s Creek,” and was anglicized by the British), Fort Christina, and New Castle.

In 1654, the Dutch drove the Swedes out from the region, but in 1664, the British successfully beat back the Dutch, gaining control of Delaware Bay’s western coast. This victory heightened King Charles II’s interest in tightly securing his newly won territory on the peninsula. The crown viewed the strategically important ports of Whorekill and New Castle as vital for regional defense, and rumors circulated that the king planned to carve out a new colony from Maryland’s charter to ensure control of these areas.
Lord Baltimore, fearing the loss of his territory and frustrated by the crown’s apparent disregard for his authority, sought a way to assert his dominance over the disputed region. He believed that if he could convince the townspeople of Whorekill to swear allegiance to the Maryland colony as its lawful government and agree to pay taxes, he would have a stronger case to present to King Charles II, hoping to prevent the subdivision of the peninsula into additional colonies.
With this goal in mind, on May 5, 1672, Baltimore sent a party of thirty horsemen—a significant force for the time—to the settlement. This expedition was intended as a show of force to back his request, in the hopes that it would frighten the townspeople into submission. However, the townspeople resisted, refusing to yield to his demands. When this strategy failed, Baltimore’s anger only grew.

The following year, Baltimore’s fury culminated in a far more savage assault. Deliberately choosing Christmas Eve, December 24, 1673, he struck on a night meant for joy and peace, ensuring the emotional and mental anguish would be as deep as the physical destruction. This calculated cruelty added a sinister twist to his vengeance, making the attack not just an assault, but a violation of the spirit of the season. He dispatched forty troopers led by Captain Thomas Howell, who “took the place by a simple show of force.” (In 1950 the Cadwalader Collection of The Historical Society of Pennsylvania published five previously unknown and unpublished depositions from which the following first-hand quotes of the carnage are drawn.)
Howell and his men were merciless. They “tortured a merchant into confessing the location of his peltry hoard [stockpile of animal skins], and by committing sundry other ‘barbarous cruelties.'” The soldiers summoned the townspeople, confiscated their arms, and delivered Baltimore’s harsh instructions: “to destroy everything on fifteen minutes’ notice—’that you must not leave one stick standing.'”
Eyewitness accounts reveal the brutality of the attack: “Soe Immediatly the houses ware by them sett on fire and Burnt downe to the Ground.” The devastation was indiscriminate, sparing no one. Even when “sume women very big with Child and others made their Addrasse to Capt Howell and Intreated him to spare one hous for their Releife in distrasse,” Howell remained unmoved. He replied that “he must obsarve his orders and that he could spare non,” adding cynically that “if God would save them one they should have it and not Else.”

In a twist of fate that the townspeople saw as divine intervention, a thatched barn miraculously survived the inferno. As another witness recounts, “A Thatch Barne standing in the Middle or betweene A Boorded Barne of Alexander Moulston that had about Two hundred Bushell of wheate unthrashe[d] in it” was spared, despite the surrounding buildings being engulfed in flames. The barn caught fire three times but extinguished itself each time, leading Howell to declare that “God had saft the Thatch Barne” and that “he did not dare to meddle anymore with it.”
After the destruction, Lord Baltimore’s forces compounded the suffering of the inhabitants by stripping them of their means of defense and escape. The depositions state that they “Carried away with them all the boats that ware in the Creeke and also the Arms belonging to the Inhabitents; soe that they ware left without Arms to defend themselves from the Indians being about sixty miles from any Inhabitents to goe to for Releife.”
The cruelty of the raid was so shocking that even the local Native Americans “wept when they saw the spoil that the Inhabitants had suffered by their owne native Country men.” This devastating onslaught marked the only time in the town’s history, past or future, when it was completely burned to the ground. Noted one deposition: “Sence that time the Lord Baltimore never by himselfe or others by his order or Authority never did settle any Government here or had any possession of this place.”

Moving into the 18th century, we find an example of Yuletide antics on a more local level. While less politically inflammatory than the previous century’s event, this incident nevertheless disrupted the community. Schoolboys have always been prone to pranks, Christmas season or otherwise. In late 18th-century Wilmington, the old shenanigan of ‘barring out’ the schoolmaster was still practiced, even if not always on Christmas Day itself.
Benjamin Ferris, in his “A history of the original settlements on the Delaware,” recounts a memorable 1787 incident where students took possession of the schoolhouse, barricading the entrances and refusing to admit the master unless he promised them a day off. The youths “had got possession of the schoolhouse and employed themselves in carrying a quantity of wood from the cellar, and piling it against the doors inside of the room. They then secured all the windows but one, which was kept open as a kind of drawbridge to go into the castle.”

The master and some elderly Quakers on their way to a meeting eventually broke the siege when they arrived at the school. One of them “procured a crowbar, and, with a crash that made every defender of the place to tremble, burst open a window, fronting on West street.” The Quakers tried and punished the offenders so effectively that “the stoutest heart ever afterwards quailed at the bare suggestion of a ‘barring out.'”

In the 19th century, a shoplifting incident in Smyrna on Christmas Eve of 1858 highlights the racial prejudices of the age and the way in which the police and the press characterized African Americans. The Smyrna Times reported that four black females from a settlement known as “Blanco” came to town “evidently intent on Christmas plunder, and right well they succeeded.” The ladies employed a tactic of distracting shop clerks while the others stole goods. “They would watch the stores, and when they found them full and the clerks in a ‘pother’ to know who to wait on first, in they would strut, and two of them station themselves at one end of the counter and two at the other, and while the first would be making some slight purchase, the other two would be bagging the goods.”
The authorities eventually caught and arrested the culprits, sending two to jail. The newspaper editor’s account of the incident is laced with derogatory terms and stereotypes, referring to the individuals as “darkies” and portraying them as cunning thieves. The editor also depicts the police in a caricatured manner, noting that “The boys and darkies were deterred from much expression or noise by the ‘Proclamation’ and the Police—the latter, however, indulged in a real, hearty old ‘corn-song,’ in full chorus [a 19th-century African American folk song genre].”

The portrayal of the police as more concerned with mocking their detainees by singing ‘corn-songs’ and deterring ‘boys and darkies’ from making noise, rather than focusing on preventing actual wrongdoing, further underscores the racial dynamics at play.
These three examples, spanning three centuries, are a poignant reminder that lawlessness has always been an unfortunate part of the Delaware Christmas season.
The Whorekill raids demonstrate how political rivalries and the desire for power and control could lead to acts of shocking cruelty and destruction. That the attacks took place on Christmas Eve adds an extra layer of emotional weight to the story. The assault left the inhabitants destitute and traumatized at a moment when they should have been enjoying the warmth and comfort of family and community.

The “barring out” episode, while less brutal than the Whorekill raids, nonetheless highlights the eternal propensity of youth to engage in troublemaking and rebellion. The fact that the boys chose to stage their “siege” on a day when the elderly Quakers were on their way to a meeting adds a touch of irony to the story.
Finally, the shoplifting case in Smyrna highlights the deep-seated prejudice that has long plagued American society, a bias that often manifests even during the supposedly joyful observance of Christmas. The police’s preference for singing taunting “corn-songs” over maintaining order further highlights the troubling attitudes of that period.
These incidents—spanning politically motivated violence in the 17th century, rebellious pranks in the 18th century, and racially charged theft in the 19th century—reflect the darker side of human nature that persists even during times of celebration. Such occurrences remind us that while Christmas is traditionally associated with goodwill and joy, it has not always been immune to the tensions and prejudices of society.
