WES was established in 1877 by Martin Henderson Winecoff. He donated the land, cut the timber, and helped build the school so his children and those in the community would have a local school to attend. The Litaker, Goodman, and Barnhardt families all assisted Mr. Winecoff with his venture. The original building was 15 feet wide and 24 feet long. Students sat on plank benches under desks that were nailed to the walls. Mr. C. J. Goodman's family also donated land and provided housing for the teachers of Winecoff.