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Wentzville High School was first established in 1896 as a 2-year high school. The high school had only three graduates in the first year of 1896: Pearl Marsch, Pearl Ball, and Emma Dula. The first principal in 1896 was professor J. Herring. The original high school building now houses the Green Lantern Senior Center in Wentzville. The first high school building burned in 1908, but it was rebuilt and continued to be used as the high school.
The high school building was expanded in 1938, and in 1939 it was reorganized as a full 4-year high school under the authority of a school board with state recognition. As Wentzville High School grew in enrollment, it moved to a couple different locations. The high school has been at its current location at 600 Campus Drive since the late 1970s, after moving from the location that now houses Wentzville Middle School.
The football field, known as Soby Field, was built in 1965 and named as a memorial to Missouri State Highway Patrol sergeant Herbert L. Sobolewski. Herbert “Soby” Sobolewski suffered a heart attack during the previous year while directing traffic near a tractor-trailer crash on U.S. Highway 40 near Wentzville.