Winfield High underwent major expansion in 2006 to compensate for the extreme overcrowding of the school and to update many of the facilities.

Winfield is a member of the Mountain State Athletic Conference (MSAC).

He unsuccessfully ran for United States president against Franklin Pierce in 1852.

Scott was the primary architect of the successful Union strategy during the Civil War but was too old to command in the field and retired in 1861.

Gil McClanahan of WCHS-TV stated that administrators at Winfield High had touted their "atmosphere of inclusion", and Mcclanahan stated that there was "unique culture among faculty, staff and students".