Founded by Professor and Mrs. Russell C. Calhoun in 1897 in Eatonville, Florida was the Robert Hungerford Preparatory High School. Eatonville was one of the first African American towns that incorporated in the United States.

Both of the Calhoun’s attend Tuskegee Institute, but only the Professor graduated and they both served as the first administrators. By 1935, the school had become the premier place for Negro learning in central Florida.

With the help of friends and relatives, in the spring of 1898, Mr. E. C. Hungerford donated to the school 160 acres of land. Hungerford owned a winter home in nearby Maitland, Florida. With the death of his son Robert from yellow fever, the donation was made in his name. Robert cared for a sick African American boy who no one else would help, even when he became ill himself.

From donors not only in Florida but throughout the country, the school was made possible. Miss Mary Brown of Winter Park gave the first cash donation and the second was by Booker T. Washington of Tuskegee for $400. The head manufacture in Troy, New York, George B. Cluett donated $8,000 for the construction of the second building and an additional $4,000 for the purchase of an orange grove near campus. In 1922, the Cluett Hall burned and was replaced by a stone structure bearing his name a year and a half later. He also contributed a large sum for the dining hall, which he insisted be name Calhoun Hall. Additionally, he gave $500 annually towards expenses for several years.

From small beginnings, by 1927, they had over 100 boarding pupils, several day students, and night classes for adults. In 1938, Orange County began making arrangements for African American high school students of Winter Park to attend Hungerford. They were bused daily.

The school embraced both college preparatory and vocational studies that including English, Latin, history, general science, biology, algebra, geometry, industrial arts, and home economics. They also taught typing, bookkeeping, agriculture, and physical education. Later classes in mechanical drawing and radio were added.

The students took part in interschool sports, such as football, basketball, and track. Out of the classroom, students were assigned “jobs and chores” to instill responsibility.  Open to the public, there were weekly Sunday afternoon Choral Concerts to give back to Eatonville and Winter Park for their involvement.

In 1950, it became a public school administered by the Orange County School Board. The school board replaced the original campus buildings with new ones and then decided to close it in 2009. The school still occupies a large parcel of land in Eatonville. In June 2019, the school board decided to put the land up for bid.

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