Settled in 1854 as Crossroads, this community became the site of Wood County's first business. Its name changed to Winnsborough in 1855, when a post office was established. In 1878, a railroad was built through town, and it became an important shipping point for timber and farming products. It was incorporated in 1901. Cotton supported the economy from the 1880s to the 1950s. In 1942, the discovery of oil revived the economy. Winnsboro serves the Tri-County area as an agriculture, oil, tourist, and medical center.