The Choptank River, winding through the heart of Maryland’s Eastern Shore, has long been a lifeline for the various communities situated along its banks. Among these communities is Caroline County, a small, agricultural region that would prove to be pivotal in America’s quest for independence. Founded in 1774, just two years before the Declaration of Independence was signed, Caroline County’s early years were deeply intertwined with the events of the American Revolution. This post explores the critical role that the Choptank River and Caroline County played during this period in the broader scope of American History. From the strategic importance of the river to the contributions of local patriots, I hope to examine how this newly established county navigated the Revolution’s hardships and developed culturally, economically, and socially around the demands of a fledgling country at war. 

Before diving in, I want to point out that researching the Revolution is more complicated than it seems. The Revolutionary War wasn’t a simple good-versus-evil story, despite what American schools may teach. People were deeply divided, and many were just trying to survive as best they could. That beg said, some sources used to support this blog post might have a pro-patriot bias. I’ve done my best to filter out unreliable information or add disclaimers, but it’s often impossible to know the true intentions or accuracy of writings from the late 18th century or later revisions.

The Revolution’s Beginnings and Broader Context 

It is also important to note that while many use the signing of the Declaration of Independence on July 4th, 1776 as a starting point for the war, violent friction was afoot much earlier.  The Boston Massacre took place on March 5th, 1770, and the Boston Tea Party followed three years later in December of 1773. Lexington and Concord, often referenced as the “first shots of the Revolution” occurred on April 19th, 1775. So it is not fair- nor accurate- to start the story of the Revolution in July of 1776. Caroline County was grouped with Dorchester, Somerset, and Worcester counties to form the 5th and final military district in the colony of Maryland, as established by the Maryland Convention during the organization of a state militia in January of 1776, months before independence was officially declared. 

As discussed in another blog post, the initial population of the land which would become Caroline County was mainly dependent on the Choptank River’s existence and its convenience for prospective tobacco planters. Because of this background, the county’s early infrastructure included many riverside warehouses and public buildings, such as Melvill’s Warehouse located at Pig Point (Denton); this warehouse actually became a vital storage facility for George Washington’s army’s supplies and provisions during the war. Due to the swift depletion of soil by tobacco plants, many Eastern Shore planters switched to more mild-mannered crops such as wheat, corn, and other produce when they realized that land on the Shore was limited. This change in agricultural focus occurred on the Eastern Shore somewhat earlier than the rest of the country, meaning that when the Revolution began, Eastern Shore farmers had already perfected growing food rather than a luxury item- something that would serve them well as food became scarce in other areas. 

The “Breadbasket of the Revolution” and Privateering

The Choptank River, along with the greater Chesapeake Bay region, was a trade hub if there ever was one. With this pre-existing setup as essentially an agricultural shipping Mecca, the Patriots were able to utilize the area as a primary supplier of foodstuffs for the Continental Army. Additionally, when America’s economy began to crumble in the chaos of war, the Eastern Shore’s successful agricultural output was a valuable economic stabilizer. This has led to the Eastern Shore of Maryland, Caroline County included, receiving the label “the breadbasket of the Revolution” from historians. This, unfortunately for the patriots, meant that the British targeted the Chesapeake Bay with both Naval vessels and privately hired Privateers. Privateering was a tactic used by warring nations in which ship captains could lease out their services as a sort of subdued pirate to plunder the commercial vessels of their enemy, with the goal of hurting their opposition economically. Although they were not necessarily permitted to take drastic measures, many of history’s finest pirates started out as Privateers (see Blackbeard or Captain Kidd).  

In retaliation, Maryland gathered its own fleet of Privateers to patrol the Chesapeake Bay and its rivers, including the Choptank. The original scrolls on which they attempted to keep track of these Privateers are preserved at the Maryland Archives. Between 1776 and 1777, a total of 39 individuals were documented as sanctioned Privateers for the Province of Maryland. This first document is hastily thrown together, including lots of shorthand writing while only listing names of captains and vessels, indicating that the situation was too dire to take the time to properly organize their information. To a historian’s eye, this could mean a plethora of things; that the British posed an early threat to the area, that mobilization for volunteers to support the cause was overwhelming, simply that Americans had little to no formal Navy and relied heavily on Privateers, or a combination of these. In subsequent scrolls, the specifics about these Privateers are much better documented. From 1777 to 1779, 104 individuals were hired as Privateers in the state, almost all of them being from Baltimore and Annapolis. More and more Eastern Shore dwellers show up as the years pass from 1779 and 1782, specifically from Dorchester and Talbot counties, implicating the Choptank River itself as being a warzone between British and Patriot Privateers. A newspaper clipping from February of 1782 reporting on the conflict specifically references that there was a ship bound for the Choptank, but it was intercepted. This report gives insight into the back-and-forth nature of the fight occurring on the high seas and in the Chesapeake region. 

  In-Fighting in Caroline County 

Denton’s own name was shaped by the conflict of the Revolution. It was originally called Edenton after Robert Eden, the last royally-appointed Governor of Maryland (who’s wife’s name was Caroline, hence Caroline County). Locals fumed at the idea of anything relating to this Governor as he was a direct representative of the King. Though he “quietly fled” in 1776, the residents of Edenton refused to call the town by this name, and instead opted for the nickname Pig Point. For some, this still was not enough. When Edenton was chosen as the county seat, residents of Bridgetown (present-day Greensboro) were repulsed by the idea, so much so that they fought to have it moved to Bridgetown, moving the seat back and forth numerous times until the Maryland General Assembly finally declared Pig Point the official seat in 1790. This tension illustrates just how deep anti-British attitudes went in the Caroline County area. Studying the broader implications of the American Revolution, historians have noted that passion for the cause was highly influenced by proximity to British troops. The closer the enemy was or the more danger a particular area faced, the patrioticness of the locals either hardened or dissolved, depending on the individual’s situation or personality. Being of a place that was a constant target and was easily accessible due to its central location and waterways, citizens of Caroline County and the surrounding areas had no choice but to be on constant alert. As architectural historian Christopher Weeks pointed out, “Lord Dunmore’s British troops posed a constant threat to this area.” It did not help that the war’s toll on local economies left many destitute, including those in Caroline County. One man wrote, “each year that this great and glorious conflict continued…depreciated Caroline’s finances until they had almost if not yet reached the vanishing point.” 

Religious Shifts 

Public sentiment against the King did not just influence politics. Anyone who has been to the Eastern Shore may note the abundance of Methodist churches that still exist today. Additionally, Caroline is known for having a Quaker population that would act as vital supporters of the Abolitionist movement in the 1850s/60s. The roots of these two religions spreading over the Shore go back to the Revolutionary Period. Maryland was founded as a supposed haven for Catholics, however by the late 18th century the most practiced religion in the colony was Anglican. And despite one of the motivators for immigration to the American territory being religious freedom, the colonial government still supported the Church of England via taxes. Obviously, issues with this system arose when the phrase “taxation without representation” became America’s mantra. To add fuel to the fire, Anglican priests had to be ordained in England, making them guilty by association when colonists began uniting against the British government and all those intertwined with it. These priests often lived relatively lavish lifestyles when compared to the common folk they led, making them unfit for the mold of a humble American countryman (more on this identity formation later). Methodism appealed to the radical colonists who saw the minimal salary of a Methodist priest- a whopping average of six dollars a year- as more acceptable. Methodists also didn’t charge a church tax that would directly benefit England. Some drifted toward Quakerism also for these reasons, especially if they also tended to oppose the war on a moral basis. Religion during the Revolution was tricky. One must put themselves in the shoes of 18th-century individuals who had been trained to fear God from the moment they opened their eyes. Each side of the war was looking for some kind of divine intervention to prove that their cause was the worthy one, and it is obvious from this physical religious shift that most people on the Eastern Shore believed that American Independence was God’s true will- and be damned if they were going to be on the wrong side of that. 

Patriotism in Caroline and Revolutionary Leaders

Caroline was especially supportive of the Patriotic cause. Even though the community was sparse, men from Caroline County gathered in 1774 at Pig Point to sign the Caroline Resolutions in response to Parliament closing the Boston Harbor after the Boston Tea Party  (more on this later). The colony of Maryland in general was no stranger to distrust of unpopular regimes- the Calvert family which held the Lord Baltimore title was wildly unpopular since the beginning of Maryland’s founding. And, as tensions grew between Great Britain and the colonies, loyalties were undecidedly tied to social class. Pre-revolutionary Caroline County seems to have been relatively poor, as we are one of the only counties in the state to not currently have lasting buildings or other infrastructure from before the Revolution. It was not until after the war was won that durable structures and dwellings were built. Some late 18th-century lower-class civilians remained loyal to the King because they saw war as a threat to their already fragile ecosystem. The cost of war, economically and physically, was unjustifiable for their families. Others became staunch Revolutionaries because their lower-class status afforded them the ability to have nothing to lose and everything to gain. Naturally, those in Caroline County related to the Patriotic side for the latter reason, as the settlement was relatively new and many residents had yet to set up an organized society with families and dependents, unlike other areas that had been settled long before. 

Along with these paupers, even the most prominent individuals in the county’s early days would later become Revolutionaries, although of much higher status- men such as Thomas Hardcastle, Charles and Henry Dickenson, William Richardson, and others. Perhaps the most well-known of these is William Richardson, so we’ll start with him. 

William Richardson was a prominent figure in the founding of Caroline County. His property was located at Gilpin’s Point near present-day Preston, where he operated a tobacco trading operation with his landing on the Choptank. He was the one who first introduced the creation of Caroline County to the Maryland General Assembly in 1773/1774. In August 1776, Richardson was commissioned as a colonel of the Eastern Shore Battalion of the Maryland Flying Camp, a regiment that notably demonstrated bravery at the Battle of Harlem Heights and earned commendation from General George Washington, according to one of Richardson’s descendant’s application to The Sons of the Revolution. Following the disbandment of the Flying Camp in December 1776, Richardson continued his service as a colonel of the re-enlisted men, forming the Fifth Regiment of the Maryland Line. In this role he commanded many of his neighbors from Caroline. In February 1777, Richardson was tasked with suppressing “Tory” (the derogatory term for Loyalist) activities in Somerset and Worcester Counties. Some of the most popular ways that loyalists attempted to sabotage American independence included depreciating American currency and funneling information to British troops, activities that occurred heavily in the aforementioned counties. When the British threatened Philadelphia in December 1777, Richardson was entrusted to relocate the Continental Treasury to Baltimore, safeguarding the nation’s finances. Following the war, in 1788, he was a delegate to the convention that ratified the United States Constitution. Between 1789 and 1793, he served as a presidential elector.  

Thomas Hardcastle was also active in the sociopolitical realm of both Caroline County’s establishment and the Revolution, although he had little to no formal military career. Born in what would become Caroline County in 1737, he would play a significant role in the American Revolution and the early political landscape of Caroline County, Maryland. In 1777, he was appointed by the court to establish a temporary location for court proceedings amidst the conflict between holding court at Pig Point and Bridgetown. Hardcastle served as the quartermaster for Maryland and was a member of the Council of Safety (a Revolutionary local government of sorts), which first convened in Denton on August 2, 1775. Before and throughout the war, he was sent to the provincial convention in Annapolis to report on what had been discussed at the council’s meetings in Caroline. Another key way in which the Choptank River was invaluable to the area, especially during the Revolution was the transportation of both soldiers and officials like Hardcastle. Family lore suggests that Hardcastle led an independent group of Patriots to join General Washington at the Battle of Brandywine, though this is unconfirmed. An assessment from 1781 indicates that Hardcastle’s assets were significantly more valuable than those of his neighbors, highlighting his prominence and wealth within the community. This assessment was done in response to a state-wide Act “ to raise the supplies for the year seventeen hundred & eighty-one”, most likely to determine what quotas each county should be meeting in order to be in good standing with the war effort. It lists each citizen and their household specifics, as well as their land and other assets (like cattle and enslaved people). While the document supports the idea that many Caroline Countians were “paupers”, Hardcastle was obviously not one of them.  He passed away in Caroline County on September 29th, 1808, and left behind many sons who followed in his footsteps of becoming successful businessmen and political leaders in Caroline. Multiple buildings belonging to the Hardcastles still stand in Caroline County. 

Beginning a long legacy of familial historical notability was Charles Dickenson, Esquire. He was appointed as one of the first Caroline County Commissioners, who would gather for the first time in March of 1774 at either Barwick’s Ordinary (a poor man’s inn and tavern) or Melvill’s Warehouse (a grain storage and tobacco processing plant), both located on Pig Point near present-day Smith Landing Road. He would be present just three months later at Melvill’s when the Caroline Resolutions were signed- in fact, he’s the one who oversaw the whole affair. Even though some colonists were prepared to rebel against the royal government, that doesn’t mean they necessarily saw themselves as declaring independence. The Resolutions begin by reinforcing the strong allegiance that those present felt towards the King, whether it was sincere is up for debate. The two following clauses read as follows: “2nd: That it is the unanimous opinion of this meeting, that the Boston Port Act is principally grounded on the opposition made by the inhabitants of that town to the Tea Duty; that the said town of Boston is now suffering in the common cause of British America, and that it is the duty of every Colony thereof, to unite in the most effectual means to obtain a repeal of the late Act of Parliament for shutting up the port of Boston. 3rd: That it is the unanimous opinion of this meeting, that if the Colonies come into a joint resolution to forbear all importations whatsoever from Great Britain, (except such articles as are absolutely necessary,) until the Acts of Parliament for shutting up the port of Boston, and for levying a duty on America, for the express purpose of raising a revenue, shall be repealed, it will be the means of preserving the liberties of North America.”

Basically, Caroline County was uniting with other parts of the colonies to oppose the closing of the Port of Boston by refusing to purchase imported British goods. It quickly became taboo to wear British clothing or to adorn oneself in unnecessary ornaments, as it was expected that each individual give any spare monies they might have towards the Revolutionary cause. A new American identity was emerging, formed around the idea of ruggedness and naturality, and anyone who deviated from this was publicly branded as a Loyalist. Little ole Caroline County participating in this colony-wide boycott of British goods and signing a document to that effect, just a few short months after being declared a county, shows how eager they were to become a part of the fold. 

Charles Dickinson’s son, Henry, also held high political stature in Caroline. In the December 19th, 1774 issue of the Maryland Gazette, he was listed as a representative of Caroline County at a meeting in Annapolis, alongside the names Benedict Brice, William Molleson, and Joshua Clarke. During the Revolutionary War, Dickinson served on the Committee of Observation and was appointed loan officer for the Continental Loan Office in 1777. From 1779 to 1789, Dickinson was Treasurer of the Eastern Shore and held various judicial roles, including justice of the Caroline County court and judge of the Court of Appeals for Tax Assessment. He also represented Caroline County for a considerable time in the Maryland Convention. Fun fact: Henry named one of his sons Charles, after his father. This second Charles Dickinson eventually moved to Tenessee where he got into a dispute over a horse race with Andrew Jackson (who would later become President of the United States) which ended in a duel. Dickinson was killed in the duel, but the bullet he shot at Jackson remained lodged in Jackson’s body for the duration of his life. 

The Legacy of the Revolution 

Several other Caroline Countians were influential during the American Revolution, and their legacies are etched into our present landscape. Matthew Tilghman was a key figure in Maryland’s revolutionary activities and was known as the “Father of the Maryland Constitution” for his role in drafting the state’s first constitution. Robert Goldsborough was a member of the Continental Congress and a lawyer who played a crucial role in Maryland’s political scene during the Revolution. Matthew Driver would become an officer and go on to sustain Willow Grove near Greensboro. Peter Harrington, the founder of Greensboro, also fought for the Patriot cause. Peter Adams became a Captain and was present at the siege of Yorktown (Adams Landing Rd. would later be named for him). William Whitely, also of Greensboro, became a Colonel and commanded other local militiamen. Thomas Carney, an African American man from Denton, served in the Continental forces from 1777 to 1783. Other men from Caroline who are documented as having served in Patriot forces include John Willis Sr., Daniel Hignutt, William Horney, Dennis Griffith, Stephen Flaharty, Joseph Peter Webb Richardson, and more. 

The Choptank River and Caroline County played a huge role in America’s quest for independence, showcasing a mix of strategic importance, agricultural innovation, and passionate patriotism. The Choptank was more than just a river; it was a lifeline that supported the Continental Army and the greater American population with food and resources, upholding the dwindling American economy as it went. From the very beginning, Caroline Countians showed support for the Revolutionary cause, through both military and political service. The Eastern Shore was certainly in a unique situation and was home to individuals on each side of the conflict, creating a quite literal tug of war. While Caroline County as an official entity was “new”, it was not peripheral in the story of the Revolution- and the Choptank River was more important than ever before. We can still see the scares- good and bad- left behind in our road names, historic places, genealogy, religion, and culture. In no way can a single blog post encapsulate all there is to know about the story of Caroline County and the Choptank during the Revolution, but this is a good place to start! 

This post was written by Kennedy Thomason of Denton, MD as a part of her grant-funded project “The River is the Center”, which explores the influences of the Choptank River on Caroline County History. To read the original post, follow her journey, and see sources related to this article, please visit her project website at

If you want to browse some more resources that relate to the Revolutionary War or local history, you can explore my Research and Resources page, starting with the Documents and Records category:

“Ata Meeting of the Committees.” Maryland Journal (Baltimore, Maryland) I, no. 33, May 2, 1774: [1]. Readex: America’s Historical Newspapers.
“Annapolis at a Meeting of the Deputies Appointed by the Feveral Counties of the Province of Maryland.” Maryland Journal (Baltimore, Maryland) I, no. 53, December 19, 1774: [2]. Readex: America’s Historical Newspapers.
“Caroline County (Maryland) Committee of Observation, Letter to the Maryland Convention, November 22, 1775.” The American Archives Collection, Northern Illinois University Digital Library, Accessed 26 June 2024.
“Caroline History: The 1600s-1800s.” Caroline County, Maryland, Accessed 26 June 2024.
Caroline County Historical Society. “Melvill’s Warehouse.” Accessed May 22, 2024.
“Great Choptank Parish.” Vestry of the Great Choptank Parish, 1975.
“In Provincial Convention Annapolis, August 24, 1775.” Maryland Journal (Baltimore, Maryland) II, no. 89, August 30, 1775: [3]. Readex: America’s Historical Newspapers.
Mitchell, Clara R. “Memories of Choptank: 1679-1930.”
MSA C467-1 Commissioners of the Tax Caroline County – Assessment Records of Choptank Hundred, 1781.
MSA SC 205-1-22 – Daughters of the American Revolution – Tombstone records copied from Old Sellers Burial Ground in Hillsboro on the bank of the Choptank River in Caroline County.
MSA SC 283-1-1 – 283-1-4 – Peggy Stewart Tea Party Chapter, Daughters of the American Revolution Collection.
MSA SC 43-1-1 Maryland State Papers – Revolutionary Papers, Box 9.
MSA SC 5598-5-3 Judge James F. Schneider Collection relating to the History of the Courts and the Legal Profession in Maryland. James F. Schneider. 1774-1989.
Norton, Paul. “Maryland in the American Revolution.” American Revolution Institute, 2009,
Weeks, Christopher. “Between the Nanticoke and the Choptank: An Architectural History of Dorchester County, Maryland.” The Johns Hopkins University Press, 1984.
Weeks, Christopher. “Inventory of Historic Sites in Caroline County.” The Maryland Historical Trust, Nov. 16, 1980.