From the blowing sails of schooners in the 1700s to the steady hum of steamboats in the 1800s, the Choptank River has been a silent witness to the evolution of vessels that carried not just goods and passengers, but also the dreams and aspirations of those who lived along its banks. As history flowed forward, so did the modes of transportation, with each wave of innovation leaving an indelible mark on the region's economic and social fabric. This post delves into the journey of progress along the Choptank River, tracing its transformation from the age of sail to modern times, and examining how this vital waterway has both shaped and been shaped by the transportation needs of each era. The impact of transportation on the Choptank extends beyond maritime vessels; railroads, bridges, and even the use of automobiles have altered the way the river is perceived and have influenced the development of Caroline County. The river was once the heartbeat of Caroline County, central to its existence and legacy, but as its role in transportation and trade has diminished, have we lost momentum in our progress and relevance?
The earliest use of vessels on the Choptank were Native American-made canoes, fashioned from whole logs with hollowed centers. Natives would use these canoes for fishing, oystering, and trade, as well as transportation between seasonal homesteads. In order to preserve the wildlife and plantlife of one area, Native American tribes would live for a couple of seasons out of the year in one area of the shore and migrate to a different area during the other two seasons, allowing the animals and plants to reproduce during their absence. Almost all of the Native Americans on the shore, while separate tribes, belonged to the same Algonquian Nation. So waterways became a vital conduit of trade and communication between these tribes. Fishing, oystering, and other methods of gleaning resources from the river required these canoes as well. As white settlers pushed upward on the Choptank River, Natives attempted to stay one step ahead, but both peoples found sharing the rich riverbanks difficult (to say the least).
During the colonial era, the Choptank River was a vital transportation route, crucial for connecting the Eastern Shore of Maryland with larger markets and ports. It facilitated the movement of essential commodities such as tobacco and grain while simultaneously creating networks between farmers, traders, and other businessmen. In the mid-1700s, tobacco was the primary cash crop, and the Choptank River played a central role in its export. The first Governor-appointed tobacco shipping point on the Choptank was designated in 1683 near “Kings Town.” Tobacco, which was so valuable that it was used as legal tender, was transported via sloops and schooners to major ports like Philadelphia, Baltimore, and Alexandria. These vessels were used to ship goods to England and the West Indies as they could withstand ocean travel. They would anchor along the Choptank at places like Gilpin’s Point (Col. William Richardson’s home near Preston), Kings Town (Kingston), and Potter’s Landing (Denton), to be loaded with goods meant for international transport. Tobacco trade in the area flourished, with the waterways making exportation easier compared to regions where goods had to be transported across land before reaching the coast. Melvill’s Warehouse in Denton, Hughlett’s at Bridgetown (Greensboro), and Richardson’s at Gilpin’s Point were the primary tobacco storing and shipping locations in present-day Caroline County. Warehouses would have been located directly on the river with an adjacent river landing or wharf to make transport as smooth as possible. The Choptank River played an even more crucial role for Caroline County farmers after the American Revolution, when the shipment of tobacco was regulated in such a way that tobacco had to pass through plants in Baltimore before being dispersed to other markets. The Choptank also saw the strategy of privateering during the Revolutionary War, with private vessels on both sides of the conflict plundering enemy trade ships until the close of the war in 1782 (ish).
It is imperative that we put our modern commodities aside for a moment and reflect on just how central the river was to everyday life prior to trains and busses and cars. Commerce wasn’t the only thing being propped up by the currents of the “Great Choptank River”- as it was called. Even trivial things such as transporting prisoners between Denton (the County seat) and Greensboro (where the only acceptable “jail” was located) during the years between the county’s founding and the finishing of necessary public buildings relied on the river. Sending goods to troops during the Revolutionary War and War of 1812 relied on the river. Staying in contact with friends and family, receiving mail or resources unavailable on the shore, traveling between cities, and everyone's livelihoods, from farmers to fishermen to merchants, relied (say it with me) on the river. Times have changed and we have created new technology, but that does not negate the fact that the Choptank River is our origin story and our greatest asset. And even that manmade technology has had to bend to this great river’s whim!
Before railroads, water transport was the fastest, cheapest, and most logistically sound way to transport both goods and people. Today we see the river as a sort of nuisance or a source of convenient pleasure. For Native Americans and colonial settlers, the river was the center of their existence. Caroline County was especially dependent on the river as it is the only in-land county on the Eastern Shore of Maryland and therefore relied on the Choptank for access to the Chesapeake Bay and eventually the Atlantic Ocean. Trade was not the only way in which the Choptank’s currents supported Caroline’s economic growth. Many grist and saw mills were constructed along the river and its tributaries, creating a prominent local industry. According to one source there were at least four mills located in the “upper” Choptank River in 1794. Linchester Mill in Preston is perhaps the most well-known of these as it remains a preserved historical site today.
As tobacco's dominance waned, new vessels and trades emerged. The Choptank River, with its ability to connect the mid-Shore and communities like Caroline County to the Bay, became a bustling waterway for transporting goods, facilitating trade, and supporting local fishing and oystering industries. The pungy was designed specifically for the Bay and its rivers to be used for the intercoastal trade of perishable goods. Pungies began sailing between Baltimore and towns along the Choptank and Tuckahoe Rivers in the late 1800s. These vessels were vital in maintaining the flow of goods between rural farms and urban markets, particularly for commodities like grain, timber, and canned goods produced at the numerous canneries in Caroline County. The pungy shipwreck displayed in Martinak State Park in Denton serves as a tangible reminder of these vessels' existence. Fun fact: pungies were sometimes used for the pineapple trade between the Chesapeake and the Caribbean islands. So while you might not picture a Civil War soldier sipping a pina colada, it was possible. Skipjacks, a staple of the Chesapeake Bay, were originally designed for
oyster dredging in the Bay's shallow waters. These vessels were repurposed during the off-season to transport goods such as fertilizer, paving materials, and oil up the Choptank. They also carried produce downriver to Cambridge and Baltimore. The technological advancements in schooner building further transformed the commercial landscape of the Choptank River. These vessels, often two- or three-masted, were primarily used for bulk freight, including grain, timber, and canned goods. Captains who owned these vessels played a crucial role in the local economy, often leasing or owning wharves and landings along the river. The eventual invention of internal combustion engines allowed schooners to navigate the narrow river more effectively, even against the current. Skipjacks, a staple of the Bay, were born out of the need for effective oyster-dredging vessels. Essentially they were more specifically designed bugeyes which became popular after the Civil War due to the state lifting some of its restrictions on oyster dredging.
Barges were also crucial in transporting bulk goods like lumber and coal along the Choptank River. Fertilizer, in particular, was highly sought after by local farmers and was transported up the river in large quantities. Large amounts of fertilizer might have been needed due to the soil-draining properties of tobacco planting, which as discussed earlier was rampant on the shore and probably had a lasting impact on the soil’s integrity. The process of unloading fertilizer from barges was labor-intensive, involving pulley systems and manual labor to move the heavy bags from the vessels to warehouses. This trade supported local agriculture and contributed to the region's economic stability, even as the river faced challenges such as siltation and freezing, which occasionally hindered transportation. Memories of Choptank, written in 1976 about the history of the Town of Choptank in southern Caroline County, mentions that the river would freeze over enough for ice skating- often prompting residents to skate to work. The Willis family journals which were written by a prominent farming family in Talbot County from 1840s-1950s also note the river freezing- foiling plans of traveling to Baltimore for business meetings or completing necessary farm work.
African Americans played a significant role in the Choptank River's maritime industry, majorly contributing to its labor force and economic activities. Enslaved and free Black people often worked together on these vessels, enhancing their exposure to freedom and aiding in escape efforts. You can read much more about this topic here. Harriet Tubman's father, Ben Ross, was an expert boat builder and Underground Railroad Agent; he serves an example of the interconnectedness of the maritime industry and freedom-seeking.
Boat building was a significant industry along the Choptank, with shipyards in Greensboro, Hillsboro, West Denton, and the Preston area contributing to the region's maritime activities from the late 1700s to after the Civil War. The Satterfield and Moore Shipyard in Greensboro, for instance, built the notable 76-foot, two-masted schooner Dexter in 1871 (which would be used by Captain Caleb C. Wheeler…you’ll read more about him later). Satterfield and Moore also produced the Olivia Davis, a three-masted wooden barque constructed in 1854 for John G. Davis, a prominent Philadelphia merchant and manufacturer. Caroline County saw a considerable amount of shipbuilding between 1771 and 1885, with 42 vessels constructed, including 33 schooners and 6 sloops. The estimated average value of a ship built in Caroline County during the 1830-1840 period was $2,500, which is about $90,280.17 today. Although the exact location of Richardson’s Boatyard is unknown, it is recognized as a shipbuilding site in the county. This shipyard was most likely on or very near Gilpin’s Point as Col. William Richardson had a tobacco storage facility and exportation set-up there. For an area with such a small population to uphold multiple successful shipyards indicates that the Choptank was prime real estate for the shipping industry, underlining the river's role as a vital trade artery. This successful business brought many long-term settlers to the area, contributing greatly to our popularity and population. As agricultural practices in Caroline County evolved, so did transportation needs. By the early 19th century, as planters diversified their crops from tobacco to wheat, fruits, and vegetables, the demand for efficient transport increased. Small, independent sailing packet boat owners began establishing connections with cities such as Philadelphia and Annapolis. This forward-thinking by sailors helped maintain the popularity of sailing vessels in the Eastern Shore trade scene despite the advent of steamboats in 1817. However, the loyalty to outdated technology could only last so long. Residents and entrepreneurs began to notice the enticing reduced travel time from the Choptank River to Baltimore that steam-powered vessels could provide. With sail, it could take days to reach larger cities, leaving passengers at the mercy of the wind, whereas steamboats were more reliable and cut the journey from Denton to Baltimore down to just one day.
Steamboats began making their mark on the Choptank River in the 1830s, revolutionizing river transport. The Maryland was among the earliest steamboats to service the Choptank River, making runs to Easton via the Tred Avon River as early as 1819. By 1830, it expanded its route to include Cambridge, and by the 1840s, steamboats such as the Maryland and the Osiris extended their reach all the way to Denton. The Cecil, under individual ownership, began its runs to Denton in 1852, and by 1861, the Kent was making regular trips as part of the newly established Individual Enterprise Line.
The Cyrus, the first steamboat to navigate up the Choptank to Denton, heralded a new era of scheduled freight and passenger services, drastically reducing travel time and saving both time and money. The introduction of steamboats also allowed for improved connections between the Choptank River and other cities in the Chesapeake region. This new mode of transport facilitated not only the movement of goods but also social interactions and business alliances, offering Caroline County residents access to more businesses, resources, educational opportunities, and better connections with loved ones who had moved away. Steamboat landings became vibrant community hubs where passengers and goods were exchanged, and local economies thrived. It was not uncommon for residents to gather to watch the steamboats enter town, especially in West Denton, where a dedicated steamboat wharf was eventually constructed.
The steamboat era saw several notable vessels operating on the Choptank River, such as the Tred Avon, Maryland, Osiris, and Cecil. The Wheeler Transportation Line, led by Caleb C. Wheeler, became a significant player, providing service between Baltimore, Denton, and Hillsboro. Wheeler was born at Gilpin’s Point and, began his career modestly as a ship's cook, eventually captaining and owning his own schooner. In 1872 he had a 76-foot two-masted schooner built which he promptly named the C.C. Wheeler. Later he would champion steamboats such as the Minnie Wheeler. Wheeler became particularly renowned for his grassroots marketing approach, with Wheeler himself often getting off his boat at Dover Bridge and walking to Easton to meet the boat again, stopping to convince the farmers and business owners he encountered to use his line to ship their goods. This personal touch helped Wheeler maintain his business even when faced with stiff competition from Western Shore companies with larger fleets. Notable captains of Wheeler’s steamers included William H. Perry, James Branford, and Charles W. Wright. Wheeler no doubt contributed greatly to the economy of the Eastern Shore. However, stories such as these (and the history books they are printed in) are often over-flattering or conveniently forgetful. We must be careful not to interpret them as accurate reflections of character. Caleb C. Wheeler was no saint- which I only found out when searching specifically in African American newspapers from the time period which circulated an article detailing a civil court case brought against him by an African American woman whom he employed. He apparently beat the woman harshly and was found liable, making him the first white man in the state of Maryland to be successfully sued by a Black woman. But of course, that note wasn’t published in the same text as the anecdote about his small-business-saviorhood. Let this serve as a cautionary tale not to believe everything you read, even if it’s in a history book.
Steamer travel slowly progressed into a pretty lucrative affair, but many Eastern Shore residents could not afford the higher-class passenger steamers complete with staterooms and dining cabins- at least not often. A trip between Baltimore and Hillsboro cost 50 cents, which included a berth in the cabin. For an additional 50 cents, passengers could upgrade to a stateroom, with meals costing another 50 cents. For those willing to forgo the comforts of a cabin, deck passage was available for just 30 cents. Travel to intermediate stops along the river (Oxford, Easton, Cambridge, etc.) was even less expensive. Freight charges in 1890 were four cents per bushel of grain and eight cents per box of peaches. By 1895, steamboats like those operated by the Wheeler Transportation Line made regular stops at numerous landings, including Medfords Wharf, Lloyds, Dover Bridge, and Hillsboro, among others. To give you an example of the timing of steamer travel: Wheeler’s steamers would leave Hillsboro on any given Saturday at 4 pm, and would not arrive in Baltimore until Sunday around 8 pm.
Despite Wheeler's efforts, the competition among steamboat lines on the Choptank remained intense and ever-changing. This competition wasn't just about speed but also about winning mail contracts, freight business, and passenger loyalty. By 1883 the Maryland Steamboat Company was making up to eighteen scheduled stops along the Choptank just from Cambridge to Denton. The Joppa was built in 1885 by Harlan and Hollingsworth of Baltimore and quickly became one of the most celebrated vessels in the region. The Choptank Steamboat Company, Eastern Shore Steamboat Company, and Maryland Steamboat Company all vied for dominance, with each company eventually developing a loyal customer base. The Joppa and Cambridge often raced each other up the river as to be the first to arrive at docks full of waiting clientele.
However, by the early 20th century, steamboat operations on the Choptank River had dwindled. From 1919 to 1921, the Joppa and Avalon were down to three weekly trips up the Choptank River to Denton. The introduction of larger steamers like the Talbot and Dorchester in 1921 was expected to bolster the industry, but they instead became liabilities as they were limited by the river's narrow passages and the low-lying Dover Bridge. Windy Hill in Talbot County and the Town of Choptank in Caroline County were the farthest up-river these two beasts could go, and the already-suffering steamboat business was even closer to bankruptcy (if it wasn’t there already). Just a year later, steamboat service had largely ceased. The rise of railroads and automobiles presented significant competition. The Baltimore, Chesapeake, and Atlantic Railroad Company, boasted an extensive network and simply overshadowed the steamboat industry. Even the valiant efforts of Caroline County locals to revive steamboat travel, such as the short-lived City of Denton service in 1930, were ultimately unsuccessful. After their service on the Choptank River, the Joppa and Avalon had distinct post-service careers. The Joppa was repurposed during World War II as the USS Colonel Henry R. Casey. Meanwhile, the Avalon was sold to an African American entrepreneur who transformed it into an excursion vessel for Seaview Beach, an amusement park in Norfolk, Virginia, catering to the Black community during segregation. After its time at Seaview Beach, the Avalon was converted into a lumber barge, with its final fate remaining unclear.
In many ways, Caroline County was transformed by steamboat travel. Steamboats significantly enhanced the transport of agricultural goods, expanding and upholding the beloved industry by offering a faster, more reliable route to large markets in Baltimore and beyond. In turn, farmers utilized steam-powered vessels to receive tools, fertilizer, feed, equipment, and other resources that allowed them to stay on track with agricultural trends rather than be left behind. Prospective settlers and entrepreneurs could now see the communities along the Choptank for themselves, fueling population growth and industrialization across the Eastern Shore. Steamboat travel also strengthened social and economic ties between Caroline County and larger Chesapeake cities, making towns like Denton and Hillsboro more vibrant and connected.
By the late 19th century, railroads had begun to carve out their place in the upper Choptank area. Companies like the Baltimore, Chesapeake, and Atlantic Railroad Company responded to the growing popularity of rail by shutting down the 16 steamers they once employed in the Chesapeake Bay. Instead, they decided their funds were better spent adding to the 87 miles of railroad track which the company already owned on the Eastern Shore. The Maryland, Delaware & Virginia Railway Company (MD&V), backed by the Pennsylvania Railroad, followed in these footsteps. Railroads ensured that even inland areas were part of a broader commercial network of the Chesapeake region, but the steamboat industry paid the price.
Although residents of Denton made a valiant attempt to keep steamboats afloat, this effort was short-lived. The convenience and speed of automobiles and trains ultimately prevailed. The construction of a railroad bridge over the Choptank River by the Queen Annes Railroad Company further sealed the fate of steamboat travel. This bridge, still visible today just north of the Choptank River Yacht Club, was originally a manually operated turnstile bridge and played a crucial role in beach-bound travel from Love Point in Kent Island to the Deleware shoreline in the early 20th century. Even back then, the town found itself at the mercy of beach traffic!
The rise of the automobile also brought about significant changes to the local economy. As internal combustion engines became the norm in agriculture, personal transportation, and industry, the demand for fuel skyrocketed. This led to the establishment of oil storage facilities in strategic locations along the Choptank River, such as West Denton and Greensboro. Major oil companies like Standard Oil set up operations in these areas, with barges regularly navigating the river to keep the tanks full well into the 1940s. This shift from river-based transportation to roadways marked a new chapter in the region’s economic development, with roads and bridges gradually taking over as the primary means of moving goods and people.
The construction of bridges over time has had a lasting impact on the way we view the river. Bridges in early America were not completely useless, they were a part of conjoining communities just as much as early roads were- despite the fact that maritime travel was seen as superior. In 1793, the actual borders of Caroline County were altered to incorporate more of Dorchester County near Hunting Creek due to the rebuilding and retracing of a road and bridge. The need for reliable river crossings (as opposed to unreliable sailing or ferry services or unsafe, makeshift crossings) led to the passage of several legislative acts, including one in September 1704, which mandated the construction of “good and substantial bridges” over rivers, creeks, and swamps. Another act in November 1798 echoed this sentiment, reinforcing the need for improved transportation routes. The first bridge over the Choptank River was built in the 1730s at Greensboro. By August 1786, the importance of these river crossings was recognized when a notice of intent was issued by the Maryland General Assembly to pass an act for public buildings at Choptank Bridge. The first bridge over the Choptank in Denton, constructed by the Denton Bridge Company and completed in 1813, was Maryland’s first moveable bridge on the Eastern Shore. Authorized by an 1808 Act of the Maryland General Assembly, this narrow, one-lane iron bridge featured a twenty-six-foot-long pivot draw to allow boats to pass. The construction was funded by the sale of six hundred shares at five dollars each, totaling three thousand dollars. The bridge was a toll bridge, with non-Caroline County residents charged twenty-five cents for a four-wheeled vehicle, twelve-and-a-half cents for a two-wheeled vehicle, and six-and-a-quarter cents for a horse and rider. Foot passengers paid three cents, while the toll for mules or horses was two cents each. In 1818, these tolls were doubled. However, by 1849, local citizens successfully petitioned the General Assembly to buy the bridge, making it public and removing the toll. The iron drawbridge in Denton, which was erected in 1875 and later replaced by a concrete bridge in 1913, exemplifies the transition between bridges being a convenient alternative to water travel and being the main connectors of locales.
We owe our very founding and establishment to the Choptank River. It is what gave us purpose, prestige, functionality, and relevance. Our county’s infrastructure was built around the river- a trend that continued into the 1900s and one could argue continues today. Our history, culture, economy, and heritage all stream from the banks of the Choptank River. But that fact seems to get lost in all the hustle and bustle of the modern-day world. Boats and ferries operating as the primary means of transportation up until the 1920’s meant that residents, no matter their walk of life, had to coexist with the river. However, railroads and bridges have ensured that many Caroline Countians today do not necessarily have to interact with the river at all. Is that for better or worse? You can decide.
Sources:
Schneider, James F. MSA SC 5598-5-3 Judge James F. Schneider Collection Relating to the History of the Courts and the Legal Profession in Maryland. 1774-1989.
Stewart Collection. MSA SC 77-1-1 Patent, Joseph Richardson, Resurveyed Land, Caroline County. Parchment.
Mitchell, Clara R. Memories of Choptank: 1679-1930.
Weeks, Christopher. "Inventory of Historic Sites in Caroline County." The Maryland Historical Trust, 16 Nov. 1980.
MSA SC 5598-5-3 Judge James F. Schneider Collection Relating to the History of the Courts and the Legal Profession in Maryland.
"Upper Choptank and Tuckahoe River Cultural Resources Inventory." Choptank River Heritage, Choptank River Heritage Network, 2014, https://choptankriverheritage.org/Documents/Upper%20Choptank%20Tuckahoe%20Inventory.pdf.
"Memories of Joppa and Avalon." Caroline History. https://carolinehistory.org/memories-of-joppa-and-avalon/
"The Bustling Port of West Denton in the 1920s." Esri Story Maps. https://storymaps.arcgis.com/stories/376af900b1604bf8a5530cd8782ec3b2
"Bugeye." Wikipedia, The Free Encyclopedia. https://en.wikipedia.org/wiki/Bugeye
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