Brandy Station (June 9, 1863, Virginia)

Sometimes called the Battle of Fleetwood Hill, this was the first of the Gettysburg Campaign battles. Occurring in Culpeper County, Virginia, the Union cavalry corps under Major General Alfred Pleasonton launched a surprise attack on Major General James Ewell Brown "J.E.B." Stuart's cavalry at Brandy Station at dawn on June 9, 1863. After an all-day fight in which fortunes changed repeatedly, the Federals retired without discovering Lee's infantry camped near Culpeper.

The Battle of Brandy Station was the largest cavalry battle ever fought on the North American Continent. Of the 22,000 soldiers involved, about 17,000 were of the mounted branch. Some 1,090 soldiers lost their lives in the battle.

Winchester II (June 13-15, 1863, Virginia)

The Second Battle of Winchester, also referred to as the Frederick County or Winchester Battle, occurred in Frederick County, Virginia on June 13-15, 1863. After the Battle of Brandy Station several days earlier on June 9th, General Robert E. Lee ordered the II Corps, Army of Northern Virginia, under Lieutenant General Richard S. Ewell, to clear the lower Shenandoah Valley of Union opposition.

Ewell’s columns converged on Winchester’s garrison commanded by Brigadier General Robert Milroy. After fighting on the afternoon of June 13 and the capture of West Fort by the Louisiana Brigade on June 14, Milroy abandoned his entrenchments after dark in an attempt to reach Charles Town. General Edward "Allegheny”  Johnson’s division conducted a night flanking march and before daylight of the 15th cut off Milroy’s retreat just north of Winchester at Stephenson’s Depot. More than 2,400 Federals surrendered. This Confederate victory cleared the Valley of Union troops and opened the door for Lee's second invasion of the North. Of the 19,500 troops involved, the total loss was 4,709, of which 4,443 were Union and just 266 Confederate.

Aldie (June 17, 1863, Virginia)

Taking place in Loudoun County, Virginia, Major General James Ewell Brown "J.E.B." Stuart's cavalry screened the Confederate infantry as it marched north behind the sheltering Blue Ridge. The pursuing Federals of Brigadier General Judson Kilpatrick’s brigade, in the advance of Brigadier General David M. Gregg's division, encountered Confederate Col. Thomas Munford's troopers near the village of Aldie, resulting in four hours of stubborn fighting. Both sides made mounted assaults by regiments and squadrons. Kilpatrick was reinforced in the afternoon, and Munford withdrew toward Middleburg. Some 250 men lost their lives in the skirmish.

Middleburg (June 17-19, 1863, Virginia)

On the same date as the Battle of Aldie, another was also taking place in Loudoun County in Middleburg. Major General James Ewell Brown "J.E.B." Stuart, screening Robert E. Lee's invasion route, sparred with Major General Alfred Pleasonton's Union cavalry. On June 17, Col. Alfred Duffié’s isolated 1st Rhode Island Cavalry Regiment was attacked by the brigades of Confederate Colonels Thomas Munford and Beverly Robertson. The 1st Rhode Island Cavalry was routed, taking about 250 casualties. On June 19, Colonel J. Irvin Gregg’s brigade advanced, driving Stuart's cavalry one mile beyond the town. Both sides were reinforced, and both mounted and dismounted skirmishing continued. Stuart was gradually levered out of his position but fell back to a second ridge, still covering the approaches to the Blue Ridge gap. Some 390 soldiers lost their lives during the battle.

Upperville  (June 21, 1863, Virginia)

Two days later, yet another battle would be fought in Loudoun County, Virginia on June 21, 1863. In the Upperville Battle, the Union cavalry made a determined effort to pierce Major General J.E.B. Stuart's cavalry screen. Stuart had been fighting a series of delaying actions in the Loudoun Valley, hoping to keep Union General Alfred Pleasonton's cavalry from discovering the location of the main body of Robert E. Lee's Army of Northern Virginia, much of which was in the Shenandoah Valley just west of the small village of Upperville.