Late in the evening of May 15th, 1863 Capt. R. Preston Chew of Jefferson County led a squad of 45 men into Charles Town. Approaching from the east, they left their horses near the home of Andrew Hunter. Walking down Liberty Street, the turned south on George Street towards the courthouse. Union soldiers were quartered in the courthouse and the Carter House. The Union sentinel fired on the Confederates and a hot exchange ensued. Chew’s forces overpowered the Union soldiers and captured 60 men and 75 horses. “This capture was made without a single man being killed or wounded on either side.”
On October 18th, 1863, Gen. John Imboden marched to Charles Town to capture the 9th Maryland Infantry, commanded by Col. Benjamin L Simpson, garrisoned in and around the courthouse. Imboden’s line stretched from Potato Hill on the west of town to Tates’ woods on the east. Imboden’s artillery barrage succeeded in dislodging the Union troops. Fleeing Union soldiers were taken prisoner as they ran from the courthouse toward Harpers Ferry. Unfortunately, Imboden’s artillery destroyed the courthouse.
On November 19th, 1864, Capt. George Baylor with 30 men of Company “B,” 12th Virginia Cavalry entered the camp of the 12th Pennsylvania Cavalry bivouacked at Charles Town. When the Union troopers awakened a sharp fight occurred. Several Union cavalrymen were quartered in a stone house. Attempting to neutralize fire from the house, George Baylor led a charge of Confederates that included his brother, Robert. Baylor and his men succeeded in capturing the Union men in the house, but his brother Robert received a mortal wound. Robert W. Baylor died in the home of Charles Town physician Dr. James Mason. A total of 11 Union soldiers were killed or wounded, 27 were taken prisoner, and 37 horses with equipage were taken. “If the Twelfth Pennsylvania Cavalry cannot keep that country clear of guerillas, I will take the shoulder straps off every officer belonging to the regiment and dismount the regiment in disgrace.”