It was early in 1782, and the Revolutionary War had been raging for seven long years when 21-year-old Deborah Sampson disguised herself as a man named Robert Shurtleff and enlisted in the Fourth Massachusetts Regiment of the Continental Army. Before long, she found herself stationed in the Hudson Valley, at West Point. It was a wild and lawless region known as “Neutral Ground,” and its residents were often terrorized by raiding parties on both sides of the conflict.

According to historian Harry Schenawolf, writing for the “Revolutionary War Journal” in July of 2019, “during the American Revolution (1775-1783), cowboys were roving bands of Loyalists or Tories in what has become known as partisan groups. For citizens of Westchester County, whose only concern in the war was to be left alone, not taking either side, their worst nightmare bore out. Far more terrifying than being caught in the crossfire of battling troops, was the expectation that at any moment, a group of banditti thugs would swoop down, bust in your door in the name of the crown or patriotism, take all you had, clean out your barn of supplies and livestock, and if you were fortunate, you and your family would escape with your lives. It was terrorism pure and simple and both Americans and British condoned it.”

The website for George Washington’s Mount Vernon notes that, “from April 1782 to August 1783, [General] Washington lived at the Hasbrouck residence, not far from the New Windsor Cantonment, where Sampson spent the winter of 1782. While there, she served as a waiter to General John Paterson whenever she was not on missions with the Light Infantry Troops.

“While serving in Neutral Ground, Sampson was part of many skirmishes against Loyalist raiders, typically referred to as “cowboys.” During one of these skirmishes, she was shot in the shoulder. Unable to seek proper medical treatment without revealing her true gender, she allegedly left the bullet in her shoulder and continued her duty as a soldier.

“Sampson served undetected until she fell unconscious with a high fever while on a mission in Philadelphia during the summer of 1783. The attending physician, Dr. Barnabas Binney, discovered Sampson’s gender while treating her. He revealed her identity to General Paterson through a letter. Sampson was honorably discharged at West Point on October 25, 1783.”

Following the war, Sampson returned to Massachusetts, married a farmer, and gave birth to three children as well as adopting a fourth. She toured the Northeast as a lecturer and was ultimately awarded a pension by the U.S. Congress as a disabled veteran due to her shoulder wound. She died in Sharon, Massachusetts in 1827. Her headstone is engraved with the notation, “The Female Soldier.”

The story of Deborah Sampson is a fascinating one, and her ties to New York are direct and well documented. And on Saturday, August 1, her story will be told at the Narrowsburg Union as part of the Sullivan County Semiquincentennial Commemoration. “A Revolution of Her Own” is co-sponsored by The Delaware Company, Bold Gold Media, and the Narrowsburg Union.

The hour-long program will be presented by the Massachusetts based group, History at PlayTM, LLC, and features the organization’s founder and Artistic Director, Judith Kalaora as Deborah Sampson. The group warns that the “program includes simulated violence. Viewer discretion advised. Rated PG.”

Kalaora established History At PlayTM, LLC in 2010 to create enriching historical entertainment. She is a Magna cum Laude graduate of Syracuse University and Shakespeare’s Globe Education Program of London, England. She has performed on international stages from London to Montreal, as well as at venues across the United States. History At PlayTM, LLC performs their expansive repertoire virtually, in-person, and via hybrid format, to audiences around the world. For more information about the group, visit its website, HistoryAtPlay.com.

She has previously portrayed Deborah Sampson at Fort Delaware Museum of Colonial History in August of 2024, and performed “Rendezvous with Rachel Revere” for The Delaware Company’s event, “The British Are Coming” at Seminary Hill in Callicoon in April, 2025.

The program at the Narrowsburg Union is scheduled for 7 p.m. on Saturday, August 1, and is free. However, pre-registration is required, and no one who is not pre-registered will be admitted. Seating is limited and will be allotted on a first come first served basis. To register for the program, email this columnist at jconway52@hotmail.com.

The Sullivan County Semiquincentennial Commission has conducted a full slate of activities all year to celebrate America’s 250th birthday, with events in virtually every corner of the county. Still to come is a commemoration of the Battle of Chestnut Woods on September 5 and a showing of the movie version of “Hamilton: The Musical” at the Narrowsburg Union on Saturday, September 19.

Visit the Semiquincentennial Commission’s website, sullivanny250.org and The Delaware Company’s website, thedelawarecompany.org for more information on upcoming programs.

 John Conway is the Sullivan County Historian. Email him at jconway52@hotmail.com.