Union Forces Commanded by: Brig. Gen. Alfred Torbert
Confederate Forces Commanded by: Maj. Gen. Thomas Rosser
**Missing and Captured
Conclusion: Union Victory
After his victory at Fisher's Hill, Maj. Gen. Philip Sheridan pursued Early's army up the Shenandoah Valley to near Staunton. On October 6, Sheridan began withdrawing, as his cavalry burned everything that could be deemed of military significance, including barns and mills. Reinforced by Kershaw's division, Early followed. Maj. Gen. Thomas Rosser arrived from Petersburg to take command of Fitz Lee's cavalry division and harassed the retreating Federals.
The Battle of Tom's Brook occurred on October 9, as Gen. Philip Sheridan marched north through the Shenandoah Valley. His army burned barns and fields, leaving the Valley a "barren waste." Gen. Wesley Merritt moved along the Valley Pike, pursued by Gen. L.L. Lomax. Gen. George Custer rode along the Back Road west of the pike; an old classmate of his, Gen. Thomas Rosser, was close behind.
Rosser, now expected to be the "Savior of the Valley," had taken command of the Confederate cavalry and was under orders to "pursue the enemy, to harass him, and to ascertain his purposes." Rosser and Lomax followed the Union forces, engaging them at various places along the way. When none of these early clashes proved decisive, Sheridan decided to force a real fight. He told his cavalry commander, Gen. Alfred Torbert, to "either whip the enemy or get whipped yourself."
On the evening of October 8, the two forces were camped by Tom's Brook. The Confederates were to the south, while the Federals were to the north, beyond Mount Olive. The Confederates were positioned on a high ridge of hills overlooking the Tom's Brook crossings. Their line was not anchored soundly, and they were 20 miles north of the main Confederate army, so reinforcements were not readily available. On the other side of Tom's Brook, Custer and Merritt joined their lines along a firm front. General Torbert reinforced Custer and Merritt with 4,000 more men.
The next morning, fighting resumed along the pike. Merritt forced a crossing of the brook and engaged the Lomax's Confederates. The Confederates held the Union advance and there was a lull just as fighting began to the west on the Back Road.
Maj. Abram Krom led the Federal advance on Custer's front. He encountered skirmishers who retreated to the main force behind a stone fence. Custer ordered his artillery to fire on Confederates guarding the brook crossing. Confederate artillery fired back. Custer then moved a brigade to silence the Southern guns. Only 1 regiment, the 18th Pennsylvania, was able to advance. This regiment was stopped in front of Confederate Gen. Thomas Munford's troops, who stalled the Union advance for 2 to 3 hours.
To end the stalemate, Custer sent 2 regiments to the Pennsylvanians' support. They were told to flank the Confederates. When the charge sounded, the Union troops finally met with success, breaking the Confederate line and sending it reeling. During the pursuit, Union troopers captured wagons, supplies, and ambulances. When it was over, the entire Confederate wagon train and six cannons had been captured.
Union cavalry dubbed this battle the "Woodstock Races." Custer stated that, "never since the opening of this war had there been such a complete and decisive overthrow of the enemy's cavalry." Over 300 Confederate prisoners were captured, with little loss to Union forces.