Civil War: 1861 - 1865

At the outbreak of the Civil War, several units of Confederate infantry and cavalry were organized from Hertford County. After Union Army and Navy forces won the Battle of Roanoke Island in early February 1862 and took control of both Elizabeth City and Edenton, the Chowan River became vulnerable. To prevent the Union from advancing up the river to destroy bridges and railroads further north in Virginia, about four hundred Confederate troops were sent to occupy and protect Winton. On February 19, 1862, a flotilla of eight Union gunboats arrived in Winton on the Chowan River, exchanging fire briefly with Confederates on shore before the latter retreated to the safety of the town. The following morning, Union troops entered the town as the few hundred residents and a small force of Confederate soldiers evacuated.

Winton was the first North Carolina town to be burned by Union forces during the war. Union soldiers were ordered to burn only buildings that had been occupied by Confederate soldiers, but the order was poorly executed and nearly the entire town was destroyed. The only buildings believed to have survived were the James Rea House, located at the southeast corner of Main and Wynn streets where Gray Gables now stands (400 North Main Street), and the Old Smyrna Methodist Episcopal Church, located near the intersection of Main and Brickell streets, both no longer extant. The Union gunboats attempted to continue up the river to destroy railroad bridges, but Confederate forces had sunk debris in the river to prevent their advance, forcing them to instead return to Roanoke Island.