In 1833, Jesse Morgan, the area's first postmaster, opened the first educational institution for Duneland locals.[2] That school sufficed the community until William Thomas II donated land and offered to help build a two-room schoolhouse in 1840. When the building was finally finished in 1852, there were some local complaints of "its rickety conditions." Twenty-five years later, in 1877, $6,000 was spent on creating Chesterton's first high school. Within only a few years, overcrowding became a problem, and the school received a four-room addition in 1890.[3]
This building worked for some time, but complications such as a broken furnace, led to the school building being torn down in 1911. After some property disputes with a local church, it was replaced with a more spacious, two-story school. The community outgrew this school yet again, and in 1921 a school was created specifically for high-schoolers. The school was three stories tall and possessed an auditorium that could seat 750. After spending $175,000, Westchester Township High School opened on December 14, 1922, and was hailed by locals as a wonderful building.[4]
WDSO 88.3 is a radio station located at Chesterton High School, with its transmitter located at Chesterton Middle School. WDSO is a non-profit high school station.[13]