[2] That school sufficed the community until William Thomas II donated land and offered to help build a two-room schoolhouse in 1840.

After spending $175,000, Westchester Township High School opened on December 14, 1922, and was hailed by locals as a wonderful building.

[4] Chesterton offers fifteen Advanced Placement exams: Biology, US History, Literature and Composition, AP Calculus AB, AP Calculus BC, Chemistry, Stats, Computer Science, European History, AP United States History, Environmental Science, Physics, Physics B and Physics C.[5] Beginning in the 2009-2010 school year, Chesterton High School also began offering International Baccalaureate diplomas.

[6] The high school also offers dual credit through Purdue Northwest and Ivy Tech Community College for select courses.

[5] Juniors and seniors also have the ability to take vocational classes through the Porter County Career and Technical Center.