Battle of Tom's Brook

A pencil sketch on green paper shows a cavalry officer bowing his horse in respect.
General Custer saluting Confederate General Rosser at the Woodstock races, Oct. 9, 1864, sketch by Alfred R. Waud

Library of Congress

“My men could see that their only chance was in a run... and a quick one at that.”

Confederate Col. Tom Munford

Confederate horsemen were already reeling from their defeats at Third Winchester and Fisher’s Hill. The Battle of Tom's Brook on October 9, 1864 showed again how Federal cavalry had gained superiority. Called the “Woodstock Races” because Federal cavalry chased their opponents as far south as Woodstock, the loss at Tom's Brook did irreparable damage to the morale of Gen. Jubal Early's cavalry.

Tom's Brook Battlefield

Most of Tom's Brook Battlefield is privately owned but over 500 acres are preserved. A walking trail leads to a historic marker at Shenandoah County Park. Visit Tom's Brook Battlefield »

October 9, 1864

In the second week of October 1864, after destroying the resources in Virginia’s Shenandoah Valley during “The Burning,” US Gen. Philip Sheridan pulled his Army of the Shenandoah back north. As he did, Confederate Gen. Jubal Early’s Army of the Valley cautiously pursued, his cavalry nipping at Sheridan’s heels.

The Confederate cavalry commander, Gen. Tom Rosser, felt his orders from Early were quite clear: “I wish you to continue the pursuit and harass the enemy as much as possible.” Rosser’s counterpart was Gen. Alfred Torbert, and on October 8, 1864, as Sheridan’s army approached Strasburg, Virginia, fighting between Federal cavalry broke out near Tom’s Brook, a small village approximately six miles south of Strasburg.

Some of Rosser’s men felt they were pressing ahead too much, too far away from the rest of the Confederate army, then some twenty miles further south. If Rosser ran into trouble, Confederate infantry would never be able to come to their aid in time. Nonetheless Rosser maintained a position south of Tom’s Brook, his own division under Col. Tom Munford, along the Back Road, and Gen. Lunsford Lomax’s division along the Valley Pike. Facing Munford was Rosser’s West Point classmate, Gen. George A. Custer, and facing Lomax was Gen. Wesley Merritt.

Sheridan, while pleased with how his army’s withdrawal north had gone, was not happy at all with how much Confederate cavalry had plagued that withdrawal. Calling Torbert to his headquarters that evening, Sheridan vented, and ordered his cavalry chief to “go out there in the morning and whip that Rebel cavalry or get whipped yourself!” Torbert immediately issued orders to Custer and Merritt to do just that.

Around 6 a.m. on October 9, 1864, Custer’s troopers started forward along the Back Road towards Tom’s Brook. In the lead was Col. Alexander Pennington’s brigade, followed by Captain Charles Peirce’s horse artillery, with Col. Willam Wells’s brigade in support.

As the Federal cavalry approached, Rosser recognized his academy classmate, Custer, leading his men. Custer saw Rosser, too, and in the spirit of the chivalry of old, Custer stopped his horse, took off his hat, and bowed, shouting: “Let’s have a fair fight and no malice!” Rosser responded in kind, bowing, and the troopers of both sides “sent up a deafening cheer.” A strange war, indeed.

Once Merritt had connected with Custer, the Federal cavalry began a general advance. Pennington’s men overran Confederate skirmishers from the 35th Virginia Battalion, but as his 18th Pennsylvania moved ahead on the Back Road, they were stopped by the 1st and 2nd Virginia Cavalry. Further east, US Col. Charles R. Lowell’s Reserve Brigade pushed south on the Valley Pike, while west of the Pike, Col. James Kidd’s and Gen. Tom Devin’s brigades did the same. Although Lomax only had two of his four brigades - well under 1,000 troopers - they obstinately blocked Lowell’s advance, so Devin was ordered to see if he could outflank Lomax’s left. Custer wasn’t having much luck either, and as the morning slipped away, he decided to send all of his men ahead, and try to work around Rosser’s left flank. With Kidd’s support on his left, Custer ordered Pennington and Wells to press ahead, sending the 18th Pennsylvania, and 8th and 22nd New York to the west, in an attempt to get on Rosser’s flank. 

The action heated up, with Peirce’s guns firing relentlessly, and Confederate Major James Breathed’s artillery firing back in response. All along the Federal line, their greater numbers began to tell, and gradually the Confederate cavalry was pushed back. With this increased pressure, Custer personally led the 5th New York Cavalry in “one of the most splendid charges they ever made.,” racing up the slope just south of the Brook. The fighting intensified, with Munford’s troopers resisting as best they could. But then, as if scripted in a Shakespearean play, Custer’s flanking column appeared in the Confederate left rear.

Munford tried desperately to turn enough troops to face this new threat, but it proved too little, too late. Yelling at the top of their lungs, the Yankee regiments slammed into Munford’s men, and the Southern ranks evaporated. “My men could see that their only chance was in a run,” Munford admitted later, “and a quick one at that.”Nothing Rosser or any of his subordinates did helped as Federal cavalry swarmed up the slopes south of Tom’s Brook. “A panic takes the men and a scene of wild confusion ensues, the enemy closely pressing the command, which retires across the fields,” one of Munford’s staff officers wrote later, “leaving the road on which the artillery, ordnance wagons, and the ambulances with the wounded, were retiring, open..."  

Confederates abandoned artillery, as many of the Southern artillerymen barely made their escape. One of Munford’s troopers called it “undoubtedly the greatest stampede that... Brigade ever witnessed.” Many considered it a disgrace that the Confederates had run.Some attempts were made further south to make a stand, but none made much of a difference, and the retreat continued. Only Captain John Shoemaker’s artillery battery succeeded in holding back Federal cavalry, firing, then “leap frogging” all the way south to Mount Jackson. 

When Early heard of the rout, he ordered infantry north, but they were too far away to help. The Federals captured many wheeled vehicles, eleven pieces of artillery, and some 300 prisoners. Perhaps another 50 Confederates were killed or wounded, and the Federals suffered only 56 casualties, that out of over 6,500 engaged. For the Confederates it was an unmitigated disaster, and not just because of the loss of men and material.

Early was particularly critical of Rosser, as were a number of Rosser’s own officers. “Rosser should never have risked that fight,” Major Edward McDonald of the 11th Virginia Cavalry wrote later. And a private in the 3rd Virginia Cavalry agreed: “The blame rests with Rosser who is censured for being too rash.”

Rosser disagreed, of course, arguing that he was simply obeying Early’s orders to “harass the enemy as much as possible.” Perhaps, but any way one views it, this defeat hurt Early’s army, then and later. And Early’s comments didn’t help, for when he heard that Rosser’s brigade was called the “Laurel Brigade,” he responded cynically, “I never knew the laurel was a running vine. I think a pumpkin vine would be more appropriate.

Part of a series of articles titled Drive the Enemy South.

Cedar Creek & Belle Grove National Historical Park

Last updated: January 30, 2023