An Introduction
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The Battle of Jack’s Shop took place in Madison, Virginia on September 21st, 1863, when Union and Confederate forces met while marching through Madison. The battle was very bloody, especially for the Southern forces, but ended inconclusively after the badly outnumbered Confederates successfully retreated. Only one other battle took place in Madison - the Battle of James City. But the constant presence of troops, both Union and Confederate, and the large numbers of men drafted into the Confederate Army took their toll on Madison’s economy and demographics.


The largest and bloodiest battle to take place in Madison was the Battle of Jack’s Shop, On September 21st, 1863, Union Major General Hugh Judson Kilpatrick and Major Genral John Buford, Jr. moved through the town of Madison on their way to attack the Confederate army’s flank, driving out a small force of Confederates in the process. Their two divisions combined had over seven thousand men. The next morning, Confederate Major General John Ewel Brown “Jeb” Stuart, assigned to guarding Robert E. Lee’s army’s left flank from nearby Brampton, left to intercept Buford and Kilpatrick with his own three thousand troops.

On his way, Stuart received intelligence that indicated that Kilpatrick was circling around to attempt a flanking maneuver after Stuart had engaged Buford in battle. Stuart sent a dispatch to Major General Jubal Anderson Early requesting reinforcements for his badly outnumbered division, which had not fully recovered from the losses and demoralization of Gettysburg. However, Early responded saying that his troops were exhausted from previous engagements. A little before 10 A.M., Buford arrived at Jack’s Shop, at the time a village of less than ten houses.

Buford had a patrol advancing ahead of the bulk of his forces, led by Colonel George Chapman. North of the village Chapman’s patrol encountered the advance guard of Stuart’s force, who wasted no time in charging the Union troops. However, Chapman was prepared for this, and had placed a number of dismounted men in the woods next to the road to intercept any attack. The forward guard was driven back and rejoined the rest of Stuart’s forces. At the same time, Buford’s division arrived at the battle and it began in earnest. Stuart led another advance against the opposing cavalry, but heavy fire from Buford’s dismounted soldiers broke the charge and inflicted heavy casualties.

Photo courtesy Virginia Landmarks Register

Deeming further charges impossible, Stuart ordered his sharpshooters to the front in order to take advantage of the large number of dismounted cavalrymen, beginning a slow advance forward. As more men arrived on either side, the fighting escalated further, the Confederates continuing to advance until Union artillery reached the front, at which point the tide of the battle changed, with Stuart slowly falling back two hundred yards. At this point, Kilpatrick’s division was rushing to flank Stuart and finish him off. Due to the different speeds of the brigades that made up his division, Kilpatrick’s troops arrived haphazardly and far apart, allowing Stuart time to prepare a better defense.

Even so, it was clear to all that the battle would not end in a Confederate victory. Surrounded on three sides, Stuart opened artillery fire in all directions. At this point, the battle consisted less of organized, strategic movements, and more of a desperate fight on Stuart’s part to hold his battle line at all costs, and on Buford and Kilpatrick’s to break it. Stuart’s men managed to fight their way to the edge of the road and open a gap to escape, though they took heavy casualties in the process. In addition, Buford had posted sharpshooters throughout the woods to cause additional casualties among the fleeing Confederates. Stuart and his entire command survived, even successfully extracting his horse artillery.

Content in this article was taken from a senior project produced by high school student Peter Rice at the Blue Ridge Virtual Governor's School in Madison County. To see the full paper with references, please visit his project website.

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