The early to mid-1600s saw the reign of tobacco as the dominant cash crop in the American colonies. The King of England strongly opposed the growing of tobacco in the mother country, and the climate was not exactly suitable for its growth anyway, leaving the colonies as the dominant source of the coveted crop. With the high demand in both the colonies and Great Britain, its value increased quickly, and thus planting tobacco became perhaps the one true get-rich-quick-scheme of the seventeenth century. Soon enough it became the backbone of the colonial economy. The influence of tobacco eventually reached the Eastern Shore of Maryland and, one could argue, became one of the major reasons that the area was settled. In many ways, we have tobacco and its promises of luxury to thank for the founding and formation of Caroline County and the evolvement of the area over time. Of course, the Choptank River can be seen as the glue that held the international interest in tobacco and the flatlands of the Shore together. 

Even though the Chesapeake Bay was instrumental in the tobacco industry (so much so that it had its own Chesapeake Consignment System), the land we now call Caroline County was too far out of reach to catch on during the first tobacco boom. Dorchester County- then called Dorset- at the mouth of the Choptank was newly settled and coming into its own when tobacco prices took a turn for the worse in the late 1600s and into the 1730s. The creation of new plantations slowed, and some got out of the tobacco business altogether. This could be due to an array of factors. Native Americans were dying at high rates due to violence, disease, displacement, and starvation, and were therefore less available to be enslaved by white plantation owners. These planters then had to wait for imported Africans to arrive so they could purchase, enslave, and force them to work on their land. Additionally, establishing a tobacco plantation was an expensive endeavor, meaning that many were unable to afford the initial set-up. And to put it simply, tobacco was no exception to the rules of supply and demand.

     Once the prosperity of tobacco planting returned in the mid-1700s, the Eastern Shore was seen as a promising blank slate to white settlers. Areas like St. Mary’s and Cambridge were becoming too crowded, the ruling Calvert family and their Catholic religion were becoming increasingly disliked in the capital city, and the Condition of Plantation passed by the original Lord Baltimores meant that every freeborn man who promised to farm Maryland’s land would get 50 acres for himself and every adult over 16 years of age in his household- including his wife, servants, and children. He would get an additional 25 acres for every one of these persons under sixteen (at least these were the numbers in 1642, they were double before that year). Settlers decided to try their hand at sailing up the Chesapeake’s various waterways to find fertile and available land, stopping when they found the paradise they were after and claiming it as their own. Think of that song “American Kids” by Kenny Chesney: “mama and daddy put their roots right here ‘cause this is where the car broke down” (except obviously it’s a boat sailing up the Choptank). This is how English people came to inhabit the Shore and eventually Caroline County, and although not all were looking to start tobacco plantations, many others were. The easy access to the Bay and the plentiful land along the bank of the Choptank were essential for the success of farming. Unlike other colonies where land transport was necessary before goods could be shipped, tobacco could roll right out of the soil and onto a boat on the Choptank, to the Bay, and to England for distribution. Plantations were often conveniently located on the banks of the river for easy irrigation. In Maryland, tobacco was so integral that it served as legal tender- even wages could be paid in pounds of tobacco. “One pound of tobacco could buy three pounds of beef or a fat pullet, and a hogshead of tobacco shipped to England could provide a family with luxuries for a year.” The fact that there were eventually three key tobacco warehouses in present-day Caroline County is a testament to the popularity and importance of tobacco along the Choptank River. These included Melvill’s Warehouse at Pig Point (Denton), Hughlett’s at Bridgetown (now Greensboro), and Richardson’s at Gilpin’s Point.

     The population of the shore increased over the decades until complaints of travel distances to court and polling places became deafening. Those from the current locale of Caroline County had to make the trek to Queenstown or Cambridge to do business, use the courthouse, or vote. In 1773 after much petitioning from prominent Eastern Shore colonists, the Maryland Assembly granted permission for a new county to be fashioned out of land from both Dorchester and Queen Annes counties. Included in their decision was the form of payment that would be used to fund the purchase of land at Pig Point (Denton), to construct a courthouse and jail, and the assessment and recording of the land by government officials. I say that tobacco was the foundation of Caroline County’s founding because the agreed-upon fee was not in dollars or halfpennies, it was tobacco- 70,000 pounds of it- to be paid by those living within the confines of the new county lines. James Barwick, the owner of Barwick’s Ordinary (a term for an Inn and Tavern) later agreed to host court in his establishment located at Pig Point until a courthouse could be built for the low low price of 1,000 pounds of, you guessed it, tobacco.

     Tobacco remained influential in the development of the County, even as it became less and less profitable on the shore. It is probably because of the steep cost of starting a plantation that we have little to no buildings or infrastructure from the pre-Revolutionary War era in the county. All of a prospective plantation owner’s funds were used up in the purchasing of equipment, enslaved people, land, seeds, and resources, which left them with little money to build solid, long-lasting homes. Alternatively, it can be assumed that some planters never came to the region with the intention of settling permanently, they may have wanted to make their small fortune using the resources and convenience of the Choptank and leave as quickly as they came. The county’s founding occurring during the dawning days of the American Revolution did not help, as it brought widespread destitution, depreciated currency, and fractured communities. Tobacco was also known to deplete soil extremely quickly, and living on a peninsula meant that land was finite. It did not take long for colonists- and later early American citizens- to turn from tobacco to other crops to keep their limited farmlands profitable. This is perhaps why the County remains primarily agricultural today. This shift to less-demanding crops such as wheat and corn meant that the hundreds of enslaved African Americans who had previously done the exhausting work of tobacco farming on the shore were no longer necessary, leading to many enslavers freeing their slaves and contributing to a growing free Black population in the region. But that’s another story for another blog post. 

     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