The plantation was started in 1895 by Will Dockery (1865–1936), a graduate of the University of Mississippi who originally bought the land for its timber but soon recognized the richness of its soil.

[3] Dockery's land was relatively remote, but was opened up for development by a new branch of the Yazoo and Mississippi Valley Railroad, known as the Yellow Dog.

Charley Patton and his family are believed to have moved around 1900 to the Dockery Plantation, where he came under the influence of an older musician, Henry Sloan.

In turn, Patton became the central figure of a group of blues musicians including Willie Brown, Tommy Johnson, and Eddie "Son" House, who played around the local area.

With agricultural mechanisation and the employment attractions of the larger cities further north, the plantation settlements gradually disappeared, although some of the historic buildings remain.

Apart from the town’s unique historical legacy, which includes printing its own money, Dockery was home to famed bluesman Charley Patton and played a significant role in the development of the Delta blues.