Gray Gables circa 1899, located on Main Street, Winton. Designed by arcitect Samuel Sloan. Listed on the National Register of Historic Places in 1986. Photographed by wikipedia username: DaveEM1004. own work, 2021 [cc-4.0], accessed via wikimedia commons, March, 2023.
Winton was incorporated as a town in 1766, replacing Cotton's Ferry as the county seat of government. Originally known as Wynntown, it was named for Benjamin Wynn, a state assemblyman who donated 50 acres of land for a town commons. It is located along the Chowan River. In 1881 David Owen established the Owen Tobacco Company which, at the time, was the only tobacco manufacturer in northeastern North Carolina.
Located on the south bank of the Chowan River, Winton [†] was originally known as Cotton's Ferry, named for Alexander Cotton who operated a ferry across the Chowan River in this location starting in the 1740s. A small village soon formed near the ferry, and when the county was created in 1759, the state legislature directed a county court to meet at Cotton's Ferry on the fourth Tuesdays of February, May, August, and November of each year. This original county courthouse was destroyed in 1830 when a man convicted of forgery set fire to the building to destroy evidence in his case, although he was unsuccessful in avoiding conviction.
In 1766, the village of Cotton's Ferry was established as the Hertford County seat. After Alexander Cotton's death in 1765, Joseph Dickinson took over operation of the ferry. Dickinson is believed to have been the first person to be buried in Winton after his death in 1772, and his grave is in the Dickinson Cemetery at 805 North King Street in the historic district. Meanwhile, Benjamin Wynns acquired the Cotton land. Wynns was a planter with substantial landholdings in Herford County and was the colonial assemblyman who sponsored the bill that created the county in 1759. Later he served as colonel of the county's militia during the Revolutionary War. Wynns donated 150 acres for a town, which was established by an act of the state legislature in 1768 and named Winton in his honor. The act also appointed Henry Hill, William Murfree, Mathias Brickell, Joseph Dickinson, Henry King, and Benjamin Wynns to oversee the town, all of whom have present-day streets within the historic district named in their honor. At that time, Hertford County extended east of the Chowan River, with Winton in a central location. The portion of Hertford County located east of the river became part of Gates County in 1779, however, Winton remained the Hertford County seat despite no longer being centrally located. By 1820, the town included only the northernmost portion of the historic district, extending from the Chowan River southward to Wynn Street.
During the earliest decades of European settlement, the northern portion of the county, near the Chowan River, was good farmland and well-suited to plantation agriculture, producing tobacco, cotton, peanuts, corn, and soybeans, while the southern portion was primarily swampland and therefore dominated by the lumber and naval stores industries, as well as subsistence farming. Herring fishing has always been important on the Chowan River as well. Both Native Americans and early European settlers relied heavily on the seasonal arrival of large numbers of herring in the river and used barricades, traps, spears, arrows, hand nets, nighttime fires, and other means to catch them in large quantities.
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 small force of Confederate soldiers evacuated. 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.
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. Only a few buildings are believed to have survived the fire, and only one of these remains extant today. The Old Smyrna Methodist Episcopal Church, located near the intersection of Main and Brickell streets, survived the fire and was used as a temporary courthouse until 1870 when a new courthouse was built. The church was later moved and became part of the Winton Hotel, which is no longer extant. The James Rea House is also believed to have survived the fire. It was located at the corner of Main and Wynn streets, but was relocated when Gray Gables was constructed in 1899 and is no longer standing. An outbuilding from the James Rea House, believed to have been built in 1825 and used as a kitchen, is the only extant building in Winton that predates the Civil War, and it remains on the grounds of Gray Gables at 400 North Main Street today.
Rebuilding the town was slow, but a new Greek Revival courthouse was constructed in 1870, becoming the third to serve the county, followed by the Jordan & Parker Hotel and the Northcott Hotel. None of these buildings remain extant. A small number of Italianate and Victorian-styled homes were also constructed in the 1860s and 1870s. The first home to be built after the war was the Italianate-style Valentine-Brett House at 706 North Main Street about 1863, followed by the Italianate/Queen Anne-style W.P. and Hilda Shaw House at 300 North Main Street in 1869 and the Victorian/Craftsman-style Keene- Reynolds House at 500 North Main Street in 1870, all of which remain extant in the historic district today. Naval stores and grist, flour, and lumber mills were important riverfront industries during the post- war period, although no resources remain extant from these operations.
† Adapted from: Heather M. Slane, Architectural Historian and Cheri L. Szcodronski, Architectural Historian, hmwPreservation, Winton Historic District, nomination document, 2019, National Register of Historic Places, Washington, D.C.