The first African-Americans arrived in this area in 1885 as laborers for two railroads, the Orange Belt Railway and the Jacksonville, Tampa, and Key West Railroad. Many of these workers helped construct the J. T. & K. W. Railroad bridge over the St. Johns River making continuous rail travel possible between Tampa and Jacksonville.
In the 1890s African-American farm and turpentine workers settled along the Orange Belt Railroad tracks just west of Monroe Station and north of present day Bookertown. The area’s first black school was opened in 1898 by David Henry Clay Rabun for 18 children of farm workers.
In 1906, Michael Mackenzie Smith bought a large tract of pine woods which included the land that became Bookertown. Smith surveyed part of this property into lots which he sole to black farm workers. By 1910 six houses were owned by African-Americans in what was known as “Monroe’s Colored Section”.
In 1925, Reverend Henry Manning established the settlements first church nearby on Elder Road.
In 1926, The Sanford Development Company bought a large part of M. M. Smiths’s land around the Colored Section and surveyed it into parcels and platted streets for the purpose of establishing a place for African-Americans. In the same year, the county school board build the community’s first official school. In recent years this building has served as the community center. The streets were named in 1926 for distinguished personalities in African-American history.
The community derives its name from the famed Reformer and educator Booker Taliaferro Washington. However, since so many other places were named “Washington” the community was named “Bookertown”.