Jonathan Jessop:
- Wayne Davis
- Jul 22
- 7 min read
From North Carolina to York, Pennsylvania
(Above): A portrait of Jonathan Jessop, the Quaker leader, engineer, and namesake of Jessup, Maryland; a map he drew as a young boy depicting the March 15, 1781 Battle of Guilford Courthouse, fought around his family’s North Carolina farm. Jessop’s remarkable life also included careers as a clockmaker, bridge designer, B&O Railroad superintendent, horticulturist, and a figure closely connected to the early abolitionist movement. (Courtesy of State Library of North Carolina)
Jonathan Jessop, whose name was given to the town of Jessup in Maryland, was an extraordinary figure. Jessop’s life journey took him from North Carolina to York, Pennsylvania, where he made significant contributions to his community, the anti-slavery movement, and early American industry. While he’s briefly mentioned in G. Marie Biggs’ The Story of Jessup as a contractor, his life was rich with achievements beyond that role. Jessop’s story is one of innovation, leadership, and quiet dedication to justice.
Jessop was born on September 30, 1770, to Ann Matthews, a well-known Quaker preacher and traveling minister, and Thomas Jessop. The Jessops belonged to the New Garden Monthly Meeting in Guilford County, North Carolina. The Society of Friends would remain a lifetime devotion for the Jessop family. Thomas’ farm in North Carolina was the point of action during the Battle of Guilford Courthouse in March of 1781, when 10-year-old Jonathan helped the wounded soldiers into his house for treatment. Jonathan also drew one of the detailed maps depicting the battle.
Following his father’s death in 1773, his mother relocated the family to York, Pennsylvania, when Jonathan was just 13 years old. They joined her cousin, Elisha Kirk, who was a clockmaker and Quaker minister. Jessop became Kirk’s apprentice, learning the trade and honing his mechanical skills. When Kirk passed away in 1790, Jessop took over the business and began making a name for himself in the York community.
In 1794, Jessop married Susanna Updegraff, the daughter of Joseph Updegraff, a founding member of the York Society of Friends (Quakers). The couple had six children, and Jessop’s eldest son, Joseph, joined him in the clockmaking trade. Their daughter, Mary Ann, married into a family that later became involved in the abolitionist movement, continuing a family legacy of social justice.
Jessop’s Many Roles in York
Clockmaking wasn’t just a job for Jessop—it was a stepping-stone into other fields, including engineering and civic service. His shop became a hub of innovation, and he trained several apprentices, including Phineas Davis, who would go on to build the first coal-burning steam engine used by the Baltimore & Ohio Railroad. Jessop’s ability to transfer mechanical knowledge into larger engineering projects foreshadowed his future contributions to early American infrastructure.
Beyond his business, Jessop played a central role in York’s civic life. His involvement with the local fire department, later renamed the York Vigilant Fire Company, demonstrated his leadership and technical expertise. He helped repair essential equipment and served as the fire company’s president, a position of significant influence in the growing town.
Jessop also held various public offices. He served as a burgess (like a mayor) and was elected as one of the directors of the York Almshouse, a facility that provided care for the poor. His role in the almshouse aligned with his Quaker values of service and equality, reflecting a deep sense of responsibility for the well-being of his community. These leadership roles solidified his reputation as a man dedicated to both civic duty and public welfare.
Quakerism in Jessop’s Life
Jessop’s Quaker beliefs guided much of his work and decisions. In 1797, he was appointed as clerk of the York Meeting of Friends, a role he held for many years. Quakerism, with its emphasis on equality, peace, and social justice, deeply influenced Jessop’s approach to both his business ventures and public service. His leadership within the Society of Friends demonstrated his commitment to the values of humility, integrity, and communal support.
Quaker meetings often involved reflections on social issues, including slavery, and Jessop’s strong connection to this religious community informed his views on the institution of slavery. Jessop’s leadership in the Friends Meeting played an important role in shaping York’s social conscience, particularly as the town became involved in the abolitionist movement.
Innovations and Engineering Work
Before his involvement with the B&O Railroad, Jessop was already making strides as an engineer. In 1809, he became the superintendent of the York and Conewago Turnpike, where his mechanical skills came in handy as he oversaw construction and road-building projects. His work in infrastructure expanded in 1811 when he and his business partner, Michael Gardner, patented the “Balance Bridge.” This innovative design was praised for its ability to span large rivers and its durability. The patent described the bridge as “particularly adapted to large spans, from one hundred to three hundred feet,” showcasing Jessop’s forward-thinking approach to construction and engineering.
The bridge’s design and simplicity made it a critical solution for river crossings in the early 19th century. Jessop’s foundry produced these bridges, adding to his contributions to local infrastructure and his reputation as a skilled engineer.
Overcoming Setbacks and Turning to Horticulture
In 1817, Jessop’s clockmaking business and cotton venture were devastated by a major flood in York. Despite this setback, Jessop rebuilt his clockmaking business and eventually sold it to his son, Joseph, in 1823. This allowed him to pursue one of his greatest passions: horticulture.
In 1820, Jessop propagated what would later become the famous York Imperial Apple, initially called “Jonathan’s Fine Winter” for its long-lasting nature. The apple quickly gained popularity due to its ability to survive through the winter without spoiling. By 1855, New York pomologist Charles Downing renamed it the “York Imperial,” reflecting both its origins and superior quality. The York Imperial became a top apple variety in the United States and remains a beloved heirloom fruit today.
In 1926, the Pennsylvania Farmer described Jessop as “a figure as significant to Pennsylvania’s apple industry as Johnny Appleseed.” His legacy in horticulture has endured for over 200 years, and the York Imperial apple remains a symbol of his contributions to agriculture.
The B&O Railroad and Jessop’s Involvement
Jessop’s contributions to the B&O Railroad are a testament to his ability to innovate and lead. His former apprentice, Phineas Davis, designed “The York,” the first coal-burning steam engine used on the railroad. Described as a “grasshopper-style” engine due to its vertical boiler, the engine was a major success, leading to further work for Davis and his team.
After Davis’s untimely death in 1835, Jessop stepped in as Superintendent of Machinery for the B&O Railroad. In this role, he oversaw the construction and maintenance of the railroad’s engines and cars. He was responsible for ensuring that the engines were always ready for service, managing water stations, depots, and ensuring smooth operations. Jessop’s work with the B&O Railroad was critical during a period of rapid expansion and growth for the rail industry, and he held this position until 1839.
Abolition and Underground Railroad Involvement
While there is some debate about the extent of Jessop’s direct involvement in the Underground Railroad, there is significant evidence to suggest that he and his family were committed to the anti-slavery cause. Jessop’s grandson, Edward Chalfant, was known to distribute abolitionist literature and provide food to enslaved people seeking freedom. Jessop’s son-in-law, James Chalfant, reportedly helped transport fugitives to Amos Griest, a Quaker leader in York who was heavily involved in the Underground Railroad.
York, Pennsylvania, was a key stop on the Underground Railroad. According to William Still’s The Underground Railroad, Quakers like Joel Fisher and Samuel Willis were instrumental in hiding and guiding freedom seekers. Jessop’s connections to these figures suggest that he was likely involved in the broader abolitionist network, even if he was not publicly active.
One particularly compelling piece of evidence is a letter written by Yardley Taylor, a Quaker abolitionist from Loudoun County, Virginia. In 1828, Taylor wrote to Jessop asking for his help in assisting a man named Harry, who was trying to escape slavery. Taylor’s letter asked Jessop to provide Harry with a “safe private conveyance” and gave detailed instructions for Harry’s journey. While Harry was ultimately captured, the fact that Taylor reached out to Jessop for help indicates that Jessop was trusted within the abolitionist community.
York Meeting and the Testimony Against Slavery
The York Meeting of Friends consistently opposed slavery, as reflected in their meeting minutes. In August 1842, they recorded: “Our testimony against slavery is maintained,” showing their ongoing commitment to the cause. By the 1850s, the Meeting was actively providing for African Americans in their care, ensuring that they received education and support.
Jessop’s close relationships with figures like Joel Fisher and Samuel Willis further suggest that he was involved in abolitionist efforts, even if his contributions were behind the scenes. Dr. Israel Betz, writing in Friends Intelligencer in 1913, described Jessop’s home as a “beacon light” for fugitives on the road to freedom.
A Lasting Legacy
Jonathan Jessop’s life was marked by innovation, leadership, and a deep commitment to justice. From clockmaking and bridge-building to horticulture and his work with the B&O Railroad, Jessop left a lasting impact on York, Pennsylvania, and beyond. His contributions to the York Imperial Apple and his role in helping to develop the country’s early rail infrastructure are just two examples of his broad influence.
But perhaps the most important part of Jessop’s legacy is his moral integrity. His 1857 obituary praised his “genial disposition” and “freedom from prejudice,” noting that he lived “without making a single enemy.” His life serves as an enduring example of how moral conviction, community action, and hard work can shape not just a town, but the country itself.
Jonathan Jessop should be remembered not only for his professional achievements but also for his role in the fight for freedom and equality.
Read Hidden History of Howard County by Nathan Davis and Wayne Davis, published by The History Press, for more forgotten and hidden stories about Howard County.
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