Heaton's Crossroads, also known as the Purcellville Wagon Raid, was an American Civil War skirmish that took place between Federal cavalry under Brig. Gen. Alfred N. Duffié and Confederate infantry under Maj. Gen. John C. Breckinridge on July 16, 1864, near present-day Purcellville, Virginia in Loudoun County as part of the Valley Campaigns of 1864. The action was tactically inconclusive.

Following the Battle of Fort Stevens on July 12 in Washington D.C., Confederate Lt. Gen. Jubal A. Early decided to withdraw his army across the Potomac River into Virginia and return to the Shenandoah Valley. The Confederates withdrew along the Georgetown Pike into Montgomery County, Maryland towards Poolesville. On the July 14 they reached Conrad's Ferry (present day White's Ferry) and crossed making camp at Big Springs just north of Leesburg, Virginia.

Nearly a full day after Early set out towards Virginia, Union forces under Maj. Gen. Horatio Wright set out in pursuit. Under his command was the entire VI Corps, part of the XIX Corps as well as several divisions of "100-days" troops recruited to defend Washington. On the afternoon of July 15, Wright arrived in Poolesville and learned of the arrival of the Army of West Virginia at Harpers Ferry.

A small force of infantry and cavalry from the Army of West Virginia, under Brig. Gen. George Crook had crossed into Loudoun that morning by way of Berlin (present day Brunswick), briefly skirmished with Confederate cavalry near Waterford and retired to Hillsboro. Seeing that he could pin Early between himself and the force under Crook in the Loudoun Valley, Wright determined to cross the Potomac the following morning and ensnare Early in the Federal pincers. Wright, however, could not easily communicate with Crook as the telegraph wires between his position and Harpers Ferry had been cut by John S. Mosby's Rangers a few days prior during his raid on Point of Rocks.

The morning of July 16, with the Federals closing in, General Early broke camp at Leesburg and set out for the Shenandoah Valley by way of Snickers Gap which lay some 20 miles across the Loudoun Valley via the Snickers Gap and Leesburg Pike. While his main army and wagon trains used that route to withdrawal, cavalry under Brig. Gen. Bradley T. Johnson was ordered to take a more northerly route and protect the armies right flank and Brig. Gen. John McCausland was to lead cavalry, and a column of POWs and cattle captured Maryland, on a southerly route across Ashby's Gap and protect the armies left flank. The infantry of Generals Robert E. Rodes and Stephen Dodson Ramseur marched behind the wagons and Brig. Gen. John D. Imboden's cavalry served as the rearguard.

Later that morning, Wright began his crossing at Conrad's Ferry, with a small force under Maj. Gen. Edward Ord crossing at Edwards Ferry. Wright's forces briefly skirmished with Rodes and Ramseur's Cavalry, who quickly withdrew in the face of superior numbers. Though the crossing was not disputed, Wright spent the rest of the day getting his army across the river and was only at Leesburg by days end, where he briefly skirmished again with Imboden's Cavalry. While Wright was crossing the river, General Duffié dispatched several cavalry patrols from Hillsboro to locate the Confederate column. On patrol encountered Confederate Cavalry east of Purcellville and drove them back on the main body and in doing so located Early's wagon train. The patrol broke off and returned to Hillsboro to report the reconnaissance.

As the Confederates made their way across the Loudoun Valley, Johnson's cavalry stopped at Waterford to water their horses, assuming the army was in safe territory and not in imminent danger. This delay allowed the main army to advance beyond its right flank screen. Around noon, Duffié's patrols reported back to him, alerting him of the presence of the Confederate wagon train as well as of Johnson's force at Waterford. General Crook immediately dispatched the 15th New York Cavalry under Col. George Wells to Waterford to engage Johnson and the 21st New York with the 1st West Virginia Light Artillery under Col. William B. Tibbits to attack the wagon train. Wells for his part drove off the remaining Confederates at Waterford, though Johnson's main force had already left, and then stayed to receive the accolades of the unionist town's thankful citizens.

Tibbits, meanwhile, arrived a mile north of Heaton's Crossroads on the Berlin pike and caught sight of the Confederate column, which to his delight was without cavalry protection. Tibbits left a small force there as a decoy, telling them to wait for the artillery signal to attack and then took his main force a mile west through a woods, using a small ridge to screen himself from the Confederates. Tibbits deployed his men and artillery on the crest of the ridge and at 2 p.m. began his attack, ordering the artillery to fire and his men to charge. The shock of the attack caused the small infantry guard accompanying the wagon train to flee without a fight. The attacking Federals then caused the Confederate teamsters to stampede the Wagon trains, and Tibbits turned his charge to the east allowing him to round up the wagons fleeing his decoy force attacking along the Berlin Pike.