J. E. B. Stuart in the context of John Brown (abolitionist)

The Battle of Brandy Station, also called the Battle of Fleetwood Hill, was the largest predominantly cavalry engagement of the American Civil War, as well as the largest ever to take place on American soil. It was fought on June 9, 1863, around Brandy Station, Virginia, at the beginning of the Gettysburg campaign by the Union cavalry under Maj. Gen. Alfred Pleasonton against Maj. Gen. J. E. B. Stuart's Confederate cavalry.

Union commander Pleasonton launched a surprise dawn attack on Stuart's cavalry at Brandy Station. After an all-day fight in which fortunes changed repeatedly, the Federals retired without discovering Gen. Robert E. Lee's infantry camped near Culpeper. This battle marked the end of the Confederate cavalry's dominance in the East. From this point in the war, the Federal cavalry gained strength and confidence.

Hit-and-run tactics are a tactical doctrine of using short surprise attacks, withdrawing before the enemy can respond in force, and constantly maneuvering to avoid full engagement with the enemy. The purpose is not to decisively defeat the enemy or capture territory but to weaken enemy forces over time through raids, harassment, and skirmishing and limiting risk to friendly forces. Such tactics can also expose enemy defensive weaknesses and achieve a psychological effect on the enemy's morale.

Hit-and-run is a favored tactic where the enemy overmatches the attacking force and any sustained combat is to be avoided, such as guerrilla warfare, militant resistance movements, and terrorism. However, regular army forces often employ hit-and-run tactics in the short term, usually in preparation for a later full-scale engagement with the enemy when and where conditions are more favorable. Examples of the latter include commando or other special forces attacks, reconnaissance-in-force, or sorties from a fortress, castle, or other strongpoint. Hit-and-run tactics were also used by the lightly armed horse archers, typical of the Eurasian steppe peoples, who excelled at them. That holds especially true for such troops that were not part of a large army (such as scouting parties), but it was common to see them employed in such a way even as part of a major force.

George Armstrong Custer (December 5, 1839 – June 25, 1876) was a United States Army officer and cavalry commander in the American Civil War and the American Indian Wars.

Custer graduated from the United States Military Academy at West Point, New York, last in his graduating class of 1861 (34th out of a starting class of 108 candidates, 68 passing the entrance exam, of whom 34 graduated). Nonetheless, Custer achieved a higher military rank than any other U.S. Army officer in his class. Following graduation, he worked closely with future Union Army Generals George B. McClellan and Alfred Pleasonton, both of whom recognized his abilities as a cavalry leader. He was promoted in the early American Civil War (1861–1865), to brevet brigadier general of volunteers when only aged 23. Only a few days afterwards, he fought at the pivotal Battle of Gettysburg in Pennsylvania in early July 1863, where he commanded the Michigan Brigade. Despite being outnumbered, the new General Custer defeated Confederate States Army cavalry of General J. E. B. Stuart's attack at East Cavalry Field on the crucial third day of the Gettysburg clash.