The parents of Stephen Weston Simmons were Jesse Mercer Simmons and Frances H. Northen Simmons. They were living in Sumpter County, Georgia in 1850 when the census was taken. Therefore we might assume that Stephen Weston Simmons, born in March of 1851, was born in Sumpter County. The next brother born was James Morgan Simmons, and he was born in Terrell County, Georgia in 1857. The youngest, Charles Anderson Simmons, was born in Georgia in 1859.

 By 1860 the Jesse Mercer Simmons family had moved to Holmes Valley, Washington County, Florida, on land just west of Ebenezer Baptist Church and a mile or two south of what is now Vernon, Florida, in time to be counted in the 1860 federal census.

  The older members of the family brought to Ebenezer Baptist Church, letters of recommendation from Hebron Missionary Baptist Church in Lee County, Georgia. The Ebenezer Baptist Church is still an active church. In E. W. Carswell's book, "Holmes Valley, Cradle of Christianity", he drew heavily on the minutes of this church. As a result, the index reads like a Simmons history. The membership list included, Jesse Mercer Simmons Sr., Jesse Mercer Simmons Jr., William Sampson Simmons, John Goodwin Simmons, Jesse Asberry Simmons, Franklin Ebenezer Simmons, Joel Thomas Simmons, James Morgan Simmons, Mary (Cox) Simmons, Fannie (Gainer) Simmons, Jessie Lee Simmons, Laura (Marlin) Simmons, Gertrude Simmons, Hazeltine Simmons, Hester Simmons, Lester Lamar Simmons, Lenora Simmons and Martha Addaline Simmons. There was also a C. C. Simmons and Dr. W. H. Simmons, however the last two have not been positively identified.

The family listed 800 acres of land in Sumpter County, Georgia in 1850. Deed records are missing in Washington County, Florida, before 1878. Ott Simmons said that Jesse Mercer gave each of his children 80 acres of land in the valley.

Stephen Weston Simmons had fourteen children, all of which were born in Washington County, Florida, except for Clark Howell Simmons who was born in 1893. Stephen Weston had moved his family back to Terrell County, Georgia, for an eye removal and the fitting of a glass eye. He then moved back to Washington County, Florida, where he lived until his death in 1927.