Hillsboro, originally spelled Hillsborough and named for pioneer settler Isaac Hill, is one of the oldest communities in central Georgia and the birthplace of Benjamin Harvey Hill, who served as a United States and later Confederate States Senator. Benjamin Harvey Hill attended the Hillsborough Academy, which was later succeeded by the school building that bears his name. From Friday through Sunday, November 18 through 20, 1864, the Right Wing of Union Major General William T. Sherman's army struggled through rain and muddy roads to cross the Ocmulgee River at Planter's Factory, also called Seven Islands, and then advanced on Hillsboro. The Right Wing, commanded by Major General Oliver O. Howard, included nearly 16,000 men of the 15th Corps led by Major General Peter J. Osterhaus, while Brigadier General H. Judson Kilpatrick's 5,000-man cavalry division accompanied it. Almost 12,000 men in Brigadier General Francis P. Blair's 17th Corps marched east from Planter's Factory on Saturday, November 19, before camping that night a few miles north of Hillsboro, while Kilpatrick's cavalry rode directly from Planter's Factory to Clinton that same day. Meanwhile, three divisions of Osterhaus's 15th Corps, including Howard, camped in or near Hillsboro on November 19, and the remaining division camped nearby on November 20 before following the others to Clinton. In Hillsboro, one group of Federal soldiers drove off cows, sheep, and hogs, took every bushel of corn and fodder, oats and wheat, and burned the outbuildings on Mrs. Louise Reese Cornwell's farm. When Howard and his staff stopped for tea, she prepared what food she had left and reflected on the irony that while he asked God's blessing at the table, the sky was red from the flames of burning houses. Staff officers played pieces and sang songs on Cornwell's piano, and Howard posted a guard to protect her. The previous summer Mrs. Cornwell had aided wounded Federal cavalrymen after the Battle of Sunshine Church, and in November at least one officer knew of her earlier kindness and thanked her as he passed. Captain Charles W. Wills of the 103rd Illinois Infantry Regiment also recalled a pleasant experience in Hillsboro, writing that through the kindness of Mrs. Elizabeth Celia Pye he slept in a feather bed, ate an excellent supper with the boys, and found that local residents had hidden belongings in the woods after hearing that the Federals burned houses, though foragers returned the items they found. From Hillsboro, Federal soldiers continued south toward Sunshine Church.