On January 29-30, 1864, as Windsor’s residents slept, U.S. Navy Lt. Cmdr. Charles W. Flusser led three gunboats to disrupt Confederate recruiting efforts. At dawn, USS Massasoit came up the Roanoke River and landed 500 men of the 103rd Pennsylvania Infantry, while near here Co. E, 2nd North Carolina Volunteers (U.S.), and a detachment from the 15th Connecticut Infantry disembarked from USS Bombshell and USS Whitehead. The columns, nearly 2,000 men, converged on Windsor, where residents awoke to gunfire in the streets. Confederate Capt. Byron B. Bowser and Co. B, 62nd Georgia Cavalry, defended the town and the nearby Wilmington & Weldon Railroad. Federal troops attacked down King Street, drove the Georgians, and the Confederates fled after encountering the rest of Flusser’s command. Several enslaved persons liberated themselves and withdrew with the Federals to the gunboats. Reports of the fight sharply diverged, with each side claiming victory: Pvt. Charles Lepley of the 103rd Pennsylvania Infantry wrote that his unit routed 300 Confederates, took three prisoners and brass band instruments, burned barracks, and returned to the boats, while Confederate Col. Joel R. Griffin wrote that after a two-hour fight his smaller force drove the attackers from Windsor back to their boats.