January 30, 1864
Acting on orders from General Robert E. Lee in the winter of 1863-64, Confederate forces under the command of Major General George E. Pickett were deployed throughout eastern North Carolina preparatory to as an attempt at clearing the enemy from the North Carolina coastal plain.
Union forces scattered in the eastern towns responded quickly. Just prior to midnight on January 29, 1864, three warships silently embarked from Union occupied Plymouth loaded with 1,200 Federal troops in an attempt to make a surprise attack on Windsor. A battle plan had been designed to capture 125 Confederate mounted cavalry troopers comprised of Company B of the 62nd Georgia Cavalry Regiment commanded by Captain B.B. Bowers, and his commanding officer Colonel Joel Griffin. The troopers had come to Windsor from their headquarters in Harrellsville to oversee a civil election.
The Union plan called for three prongs of attack to cut off all escape routes for the Confederates in Windsor. The USS Massasoit was directed to steam to Cedar Landing on the Roanoke River and discharge its troops before dawn. This force was to advance and cut off all escape from Windsor to the Roanoke River crossings. The USS Bombshell was to land troops before dawn at Cooper's Landing on the Cashie River. This detachment was to divide and capture both the Hoggard's Mill Bridge and the Windsor Bridge, cutting off all possible escape for the Confederates to Colerain, Edenton, and other Chowan River crossings. And at daylight, the USS Whitehead, commanded by Lieutenant Commander Charles L. Flusser, was to steam straight up the Cashie River and land at Windsor near this spot.
After the initial landing, a firefight began at Hoggard's Mill and 31 loyalist Union troops from Bertie County comprising Company E, 2nd NC Volunteers, led the successful capture of the bridge there. The early morning firing attracted the main body of Confederate troopers in town to this first phase of the battle. The main body of 1,000 Federal troops that had landed at Windsor proceeded up King Street towards the Southerner's rear. The Confederates, outnumbered nine to one in this second phase of the battle, were forced to shift to the south and the battle's third phase. Riding up Cobb's Hill, they were engaged by the detachment of Federal troops arriving from Cedar landing. Making a flanking turn west, the Confederates raced up the Lewiston Road and crossed the Cashie River at Craig's Mill where they turned and made as escape back to their base in Harrellsville.
Although successful in the landings, 1,200 Union troops captured only two civilians and three Confederate troopers. Also taken were about 40 "contraband," slaves who had asked to return with the Federal forces. These former slaves joined others from Bertie County already enlisted in the union Army, totaling 349.