John Wayland Intermediate School was one of four intermediate schools built in Rockingham county during the 1960s. In order to relieve crowded conditions in all of the high schools and in many of the elementary schools and also to provide a different type of program for seventh and eighth graders, the school board decided to build a middle school in each high school attendance area. The first of these, John C. Myers at Broadway opened in 1964. John Wayland at Bridgewater opened in the fall of 1966, with Carroll K. Jones, who had been principal at Elkton Elementary School as its first principal. Carroll Jones served as principal at John Wayland until 1969 when Jerry Wampler was named principal. An addition to the building was constructed in 1969 and a second addition in 1985. In the 1980s, the intermediate schools were renamed middle schools. Jerry Wampler served as principal at John Wayland until 1987 when James Gresham became principal. In 1989, a new Turner Ashby High School opened and John Wayland Middle School became the new John Wayland Elementary School, consolidating the old schools at Bridgewater and Dayton. The old Turner Ashby High School was converted to the new middle school for the Bridgewater-Dayton area and renamed Wilbur S. Pence Middle School.

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