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The Florida Mortgage and Investment Company deeded five acres in 1905 to Trustees John Mays, Willis G.P. Washington, Lewis Colson, Campbell Mitchell and J.P. Carter for a "colored" cemetery. The land was platted in 1910 as Oaklands Cemetery. For a few years in the late 1920s the cemetery was known as Peppermill. By 1929 it was called Woodlawn.
The earliest death date on a marked grave is 1905. Other gravestones and funeral home records indicate that at least eleven of the people buried in the cemetery were born before the end of the Civil War. One of these was cemetery trustee Willis G.P. Washington, who was born in 1851. Carrie Belle Warren's headstone shows a birth date of 1808.
Oaklands/Woodlawn Cemetery was the first cemetery formally established for the burial of Sarasota County's black residents. Thus, funeral records show that people from Tallevast to Myakka to Venice were brought to Sarasota for burial. Residents of the Johnson Camp for farm workers in Fruitville, the Bee Ridge Turpentine Camp, Laurel and Woodmere (a sawmill town south of Venice) joined those of Sarasota's Overtown and Newtown commutes in the cemetery.
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Joseph Holton was the first local African American to establish a funeral home in Sarasota. he began his mortuary practice in the 1920s with Edward Stone, who served the Sarasota community from his funeral home in Tampa. By 1930 Holton was the sole director of Holton Funeral Home and continued there until his death in 1948.
The first known African American doctor to practice in Sarasota is associated with the cemetery. Dr. Frank E.A. Simpson was the attending physician for at least two people buried there in the late 1920s.
Traditional African American burial patterns are evident in Oaklands/Woodlawn Cemetery. The strength of family blood ties often results in adult children being buried next to their parents rather than next to their spouses. The families of Sarasota pioneers Leonard and Eddie Reid and Joseph and Annie Weldon illustrate this custom.
According to funeral home records and tombstones, there were at least 1200 burials in the cemetery by 1980. There may have been additional early ones for which wooden markers have disappeared over time. Burials have also occurred since then.