[6] Benjamin Wynns, who had since acquired Cotton's property, donated 150 acres to the county for the creation of a town in the mid-1760s.

[5] In 1766 the town of Winton—originally styled Wynnton after the erstwhile landowner[7]—was established as Hertford's seat of government[6] and a courthouse was subsequently constructed.

Federal forces intervened in eastern North Carolina early in the conflict, and in February 1862 they captured Roanoke Island,[8] exposing territory along the Chowan River vulnerable to further penetration.

[9] Federal gunboats were subsequently dispatched up the river to destroy rail bridges north of Winton but were repulsed in an ambush by Confederate artillery.

The area economy continued to be based in agriculture, though the local lumber and fishing industries grew in importance in the latter portion of the 19th century.

While the town's bank failed during the Great Depression,[14] the local lumber, fishing, and shipping industries continued to be of importance into the 1950s.

In 1974, a bypass for U.S. Highway 13 was built diverting traffic around the community, leading to sharp decline in business in the town's center.

[17] The earliest buildings in the Winton Historic District reflect the Italianate, Queen Anne, and Gothic Revival styles of the mid-to-late nineteenth century.

[18] The C. S. Brown School Auditorium, Gray Gables, and King Parker House are listed on the National Register of Historic Places.

[19] According to the United States Census Bureau, the town has a total area of 0.8 square miles (2.1 km2), all land.