The town's founding required an act of persistence against the architecture of segregation. J.E. Clark and several friends attempted to purchase land to establish what Clark called a "colony for colored people," but as he later recounted, "so great was the prejudice then existing against the Negro that no one would sell them land for such a purpose." They persevered. By 1887, Eatonville was officially incorporated as a municipality, creating a self-governing community where Black citizens elected their own officials, ran their own businesses, and shaped their own civic life. A post office opened in 1889 and operated until 1918. The town was not a utopia -- poverty, limited resources, and the constant pressure of the surrounding Jim Crow world defined daily reality -- but it was sovereign territory in a region where sovereignty for Black Americans barely existed.

Eatonville's most famous resident was Zora Neale Hurston, the folklorist and author who grew up in the town and wove its rhythms, dialect, and communal life into some of the most important American literature of the 20th century. Her novel Their Eyes Were Watching God is set in Eatonville and nearby communities, many of which have since disappeared beneath the sprawl of Greater Orlando. Hurston's writing captured the porch-front storytelling, the sharp humor, and the dignity of a community that existed outside white oversight. The Eatonville Historic District, added to the National Register of Historic Places on February 3, 1998, contains 48 historic buildings, several directly connected to Hurston and the town's founding. The Moseley House Museum preserves the domestic architecture of the era. Each year, the Zora Neale Hurston Festival of the Arts and Humanities draws visitors to the streets Hurston once walked.

Before racial integration opened mainstream venues, Club Eaton was a landmark stop on the Chitlin' Circuit, the network of performance spaces where Black entertainers could perform for Black audiences across the segregated South. The club's stage saw some of the greatest musicians of the 20th century: B.B. King, Aretha Franklin, Ray Charles, Sam Cooke, Duke Ellington, Ella Fitzgerald, Billie Holiday, James Brown, and The Platters all performed there. The Robert Hungerford Normal and Industrial School, founded in 1897 by Professor and Mrs. Russell C. Calhoun, graduates of Tuskegee Institute, provided another pillar of community life. Booker T. Washington donated $400 toward its establishment. The school offered vocational and college preparation to Black students for over a century, its campus eventually growing to encompass almost 40 percent of the town's total land area before closing in 2010.

The story of Eatonville's land is the story of its survival. When Orange County Public Schools took control of the Hungerford School in 1950, they purchased its campus from a trust for approximately $16,000 with the stipulation that the land be used "for the education of Black children." Over the decades, the school district petitioned courts multiple times to reduce the acreage bound by that restriction. By 2019, the remaining parcel was appraised at $20 million. In 2023, the school board announced plans to sell it to a developer for $14 million, with proposals for 350 homes, apartments, retail businesses, and restaurants. Residents see the development as an existential threat to one of America's oldest Black communities. The town that was built because no one would sell land to Black Americans now fights to keep the land it has. Eatonville today is home to roughly 2,350 people. Interstate 4 passes through its city limits, but there is no exit -- a geographic fact that feels almost symbolic, the wider world rushing past a place that has always had to insist on its own existence.