Author: Jesse Gordon Moore
Henry Overstreet, my 4th Great Grandfather on my Mother’s side, was born on 2 February, 1763 in King William County, Virginia. He enlisted in Louisa County, Virginia, which is in the eastern part of Virginia northwest of Richmond, Virginia. His pension was granted on April 25, 1833. He is listed in the Pension Roll of 1835 as being a Private, receiving an annual allowance of $28.33 per year and had received $70.83 up to that time. He is listed as being in the Virginia line and that his pension commencement data was March 4, 1831. Henry had an uncle, Benjamin Overstreet, and a brother, Thomas Overstreet that also fought in the war.

The 1st enlistment of Henry and his brother, Thomas, probably was in Louisa County, Virginia. Henry states that he entered the service on June 1, 1780 as a substitute for William Tate of Louisa County, Virginia. This usually meant that the William Tate was paying Henry Overstreet to serve his time. William Tate was probably drafted for service but could afford to pay someone to serve for him. Henry's unit was under the command of General Stephens & Col. Spencer, as field officers. His Company officers were Capt. John Byar, Lt. Thomas Sheldon, and Ens. James Winston. The unit marched from Louisa County to Hillsborough, NC, where they learned the martial exercises. He remained there with his unit until General Horatio Lloyd Gates arrived. Gen. Gates was a British Major who retired in 1769. He came to the colonies, bought land in Virginia, and offered his services to George Washington at the outbreak of the war. Washington urged the appointment of Gates as adjutant of the army. On June 17, 1775, Congress commissioned Gates as a Brigadier General and Adjutant General of the Continental Army. He is considered to be the first Adjutant General of the United States Army.

Henry Overstreet and his unit marched through North & South Carolina. They crossed the Pedee River, on August 3, 1780 just inside the South Carolina border. They joined the regular army at Rugley Mill north of Camden, South Carolina. The advance guards had a chance meeting the evening before the battle. There was a "little" battle. The next day, both armies advanced at each other just after dawn. The British troops opened the battle, when the right flank fired a volley into the militia regiments, causing a significant number of casualties. They followed the volley up with a bayonet charge. The militia, lacking bayonets, panicked and fled before the British regiments even reached them. Only one company of militia managed to fire a volley before fleeing. The panic quickly spread to the North Carolina militia, and they also broke ranks and fled. Seeing his left flank collapse, Gates fled with the first of the militia to run from the field. Within a matter of minutes, the whole American left wing had evaporated. The Virginia militia ran away so quickly that they suffered only three casualties.
Three days after the defeat, the colonist had retreated back to the north side of the Pedee River. After gathering a good company they marched to Guilford Courthouse, NC. They remained there until the last of October, 1780. So after a five month tour, Henry was discharged.

In 1781, Henry Overstreet, served his 2nd enlistment. He joined a company commanded by Captain Bullock. This group was raised in Hanover County, Virginia. He was a substitute for a John Smith. They marched just below Richmond, Virginia. They marched to the south side of the James River and returned to Richmond. There they met up with General Marquis De Lafayett on Schoco Hill near Richmond. Thus ended the 2nd tour.

On September 1, 1781, Henry Overstreet's 3rd enlistment was under the command of Captain Haydon. He joined in King and Queen County, Virginia. They marched into Gloucester County. Henry was called to guard at York River at the mouth of the Plankdank Creek to prevent the negros from running away and join the enemy. They then marched down near Glouster town and drove the British further to keep them from getting provisions. The siege of Yorktown commenced and in two weeks Cornwallis, the British commander in chief, surrendered on October 19, 1781. They then marched down and took possession of Gloucester town. In October, Henry was discharged.

After the war, he returned to Hanover County, Virginia, his home. In 1788 he sold his property and moved to Fayette Co., KY. In 1798, Jessamine County was formed from Fayette County. He lived the rest of his life there. The Kentucky Patriot burial record has no record of his burial place.