The early history of European settlement in the area was marked by uneasy co-existence between Native Americans and European settlers. Some settlers lived peacefully with the natives. But in the 1810s and 1820s, after Native Americans allegedly harassed surveying crews, an escalating series of poorly documented skirmishes occurred between Native Americans, settlers, and militias known as the Illinois Rangers. Two pitched battles (complete with cannon on one side) occurred just south of Charleston along "the hills of the Embarras," near the entrance to modern Lake Charleston park. These conflicts did not slow European settlement. Native American history in Coles County effectively ended when all natives were expelled by law from Illinois after the 1832 Black Hawk War. With the grudging exception of Indian wives, the last natives were driven out by the 1840s.
 First settled by Benjamin Parker in 1826, it was named for Charles Morton, its first postmaster2. The city was established in 1831, but not incorporated until 1865. When Abraham Lincoln's father moved to a farm on Goosenest Prairie south of Charleston in 1831, Abe helped him move, then left to start his own homestead at New Salem in Sangamon County. Abe was a frequent visitor to the Charleston area, though he likely spent more time at the Coles County courthouse than at the home of his father and stepmother. One of the famous Lincoln-Douglas debates was held in Charleston and is now the site of the Coles County fairgrounds and a small museum. Lincoln's last visit was in 1859, when the President-elect visited his stepmother and his father's grave before setting out for Washington D.C.
 Although Illinois was a solidly pro-Union, anti-slavery state, Coles County was settled by many Southerners with pro-slavery sentiments. In 1847, the county was divided when prominent local citizens offered refuge to a family of escaped slaves brought from Kentucky by Gen. Robert Matson. Abe Lincoln, by then a young railroad lawyer, appeared in the Coles County courthouse to argue for the return of the escaped slaves under the Fugitive Slave Act in a case known as Matson v. Ashmore. As in the rest of the nation, this long-simmering debate finally broke out into violence during the American Civil War. On March 28, 1864 a riot—or perhaps a small battle—erupted in downtown Charleston when armed Confederate sympathizers known as Copperheads arrived in town to attack half-drunk Union soldiers preparing to return to their regiment. Newspaper accounts3 at the time said the Copperheads stated intention was to burn the town and "cut out the hearts of the 'damned abolitionists.'" Even the county sheriff is alleged to have fired on the soldiers. By the time the Charleston Riot had ended, nine were dead and twelve had been wounded, mostly Copperheads.
 In 1895 the Eastern Illinois State Normal School was established in Charleston, which later became Eastern Illinois University. This led to lasting resentment in nearby Mattoon, which had originally led the campaign to locate the proposed teaching school in Coles County. A Mattoon newspaper printed a special edition announcing the decision with the derisive headline "Catfish Town Gets It."
 Thomas Lincoln's log cabin has been restored and is open to the public as the Lincoln Log Cabin State Historic Site, 8 mi. south of Charleston. The Lincoln farm is maintained as a living history museum where historical re-enactors depict life in 1840s Illinois. Thomas and Sarah Bush Lincoln are buried in the nearby Shiloh Cemetery.
 On May 26, 1917, a deadly tornado ripped through Charleston, killing 50 and wounding 115.