In 1865, the federal military machine of William Tecumseh Sherman burned its way through Georgia and South Carolina in the final onslaught of this nation's Civil War. On the way to South Carolina's capital city, Columbia, Sherman's troops lingered a few days in the little railroad-stop town of Midway. During his visit, he destroyed all the plantations in the surrounding neighborhood including Woodlands, the home of the Simms family and about 70 enslaved African Americans. Some of the freedmen from Woodlands followed Sherman's liberating force; others left for Charleston, the closest familiar urban area. Some were thought to have sailed for Liberia. Many stayed in the surrounding community. A few families decided to continue to make Woodlands their home. There, they mostly worked on shares or as tenants, foraging from the land what little it had left to give.

Between 1821 and 1865, there were between 45 and 80 enslaved people living and working at Woodlands Plantation. Some traveled back and forth with the Simms family to the house on Smith Street in Charleston where the family visited during certain seasons and where they lived during the hot summer months. This house was generally left in the care of a few slaves who may have lived there permanently throughout the year.

The surnames of the original African American families who stayed on at Woodlands through much of the 20th century include Rumph, Rowe, and Laboard among others. Shortly after the war, James C. Beecher, Sub Assistant Commissioner of the Bureau of Refugees, Freedmen and Abandoned Lands, visited the plantation and made a list of freedmen who were working at Woodlands at that time. Some from this list may have also continued to live there for several years. In addition to these, others who stayed might include those with the surname Singleton, Glover, Curry, Kearse, Ramsey, Wright and Williams. Through marriage, extended families became linked to the original Woodlands families including the McCormicks, Steeles, Manigaults, Richbergs, Smalls, Thomases, Carters, Whittemores, and Orrs.

Isaac Nimmons was the esteemed coachman at Woodlands who helped manage plantation logistics, transportation, and livestock. Nimmons did not remain at Woodlands but after the war worked as a foreman on a plantation in nearby Springtown Township. Soon thereafter, Nimmons was able to buy property in the area and farmed for himself until his death in 1905. Descendents of Isaac Nimmons and the Simms family have recently "reconnected" and have shared their knowledge of their connection with each other.

In 1952, Mary Chevillette Simms Oliphant, granddaughter of William Gilmore Simms, wrote as part of the introduction to the published letters of her grandfather, a section entitled, "The Negroes of Woodlands." She states that there were 16 house and yard Negroes. Those especially noted were Isaac Nimmons, coachman of Woodlands and body servant to William Gilmore Simms; Edmund, the butler; Maum Abbey, Mrs. Simms' personal maid; Isom Glover, the torch tender; and Cinthia Curry, the head cook. Jim Rumph is described as a "general factotum" who "held a high place at Woodlands with both blacks and whites, as did his son Jim…" Maum Sallie was the head nurse. At the end of this section she mentioned all of the contemporary Woodlands families by name and wrote, "Woodlands is their home, and they are a part of the very fibre of the place."

The Simms family is descended from William Gilmore Simms a noted 19th-century literary figure. Many descendants of the enslaved people at Woodlands continue to live on or near original parts of the plantation. The Rumph family bought part of the original plantation property in 1917 and has continued to live and farm the land since that time. Others, whose parents and grandparents moved north during the great migrations of African American's from the South to the North in the first part of the 20th century, regularly visit family in the Midway area. Some have returned to live again in Bamberg and Orangeburg Counties. Older members of the families consistently identify themselves as being from "the Simms place." These families continue to use the original cemetery on the plantation property that was the burial ground of their enslaved ancestors.