Today, May 25, 1862: Confederate Victory at First Battle of Winchester

In early 1862 Union forces were strongly pushing Confederate forces out of Missouri, Tennessee and Kentucky. The Union Navy had begun blockading much of the eastern coast, around the Florida peninsula and had made their way to New Orleans.

The Confederacy needed a boost of some kind and that task fell on a 38-year-old Major General by the name of Thomas Jackson, also known as Stonewall Jackson. Jackson was tasked with defending Confederate ground in the Shenandoah Valley.

In April 1862, Jackson commanded a force of only 4,600 Confederate troops which proved insufficient to defend against the attack of Union Major General Nathaniel Banks at Winchester, Virginia. Banks was commanding a force of nearly 30,000 and easily forced Jackson to retreat.

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Over the next few weeks, Banks divided his forces, stationing some to defend key positions, leaving his main force with only 19,000 troops. At the same time, Jackson joined forces with Brigadier General Edward ‘Allegheny’ Johnson who was busy trying to ward off Union Major General John Fremont’s 20,000 troops with only 3,000 Confederate troops. At Conrad’s Store, Jackson was reinforced with the 8,000 Confederate troops of Major General Richard Ewell.

On May 23, 1862, Jackson and Banks fought at Front Royal, Virginia. This time Jackson had more troops than Banks and successfully drove the Union force northwest to Strasburg.

On May 24, 1862, Jackson caught up to the Union forces at Strasburg, this time forcing Banks to retreat north to Winchester. Jackson’s pursuit of Banks’ forces was so intense that the Union troops were forced to abandon most of the wagons and supplies which were welcomed by the Confederates. After marching over 300 miles in the past month, Jackson allowed his men a few hours to rest and take advantage of the Union supplies. The Confederates were so appreciative of the Union supplies that they started referring to the Union general as ‘Commissary Banks.’

On this day, May 25, 1862, the First Battle of Winchester took place as best described by one source:

“Phase One. US Deployment at Winchester: Banks now deployed at Winchester to slow the CS pursuit. He had two brigades of infantry under Donelly and Gordon, a mixed brigade of cavalry under Hatch, and 16 guns. Gordon’s brigade was placed on the US right on Bower’s Hill with its left flank at the Valley Pike, supported by a battery of artillery. The center of the line (Camp Hill) was held by the cavalry supported by two guns. Donelly’s brigade was placed in a crescent on the left to cover the Front Royal and Millwood roads with the rest of the artillery. At earliest light the CS skirmish line advanced in force driving the US pickets back to their main line of battle.

Phase Two. CS Advance on Front Royal Pike: During the night, the advance of Maj. Gen. Richard Ewell’s division (four brigades) reached Buffalo Lick. At dawn, he deployed his brigades astride the Front Royal Pike and advanced against the Union left flank. His leading regiments (in particular the 21st North Carolina) came under heavy fire from US forces deployed behind stone fences and were repulsed. CS forces regrouped and brought up artillery. After about an hour, they again advanced, this time sending regiments to either side of the high ground to enfilade the Union position. Donelly (US) withdrew his brigade to a position closer to town with his right flank anchored on Camp Hill. Trimble’s brigade (CS) then attempted a flanking movement to the right beyond the Millwood Road. This movement threatened the US left and rear. This movement, in conjunction with Confederate maneuvers on the left beyond the Valley Pike, caused the Union line to collapse in this sector.

Phase Three. CS Advance on Valley Pike: In conjunction with Ewell’s advance on the Front Royal Pike, Jackson advanced the Stonewall Brigade on the Valley Pike at early dawn in a heavy fog. At Jackson’s command, the brigade swept over a hill to the left of the pike, driving off the US skirmishers who held it. Jackson quickly placed a section of artillery on the hill to engage US artillery on Bower’s Hill at a range of less than half a mile. Union sharpshooters along Abrams Creek began picking off the cannoneers. In response, Banks moved his artillery farther to the right to enfilade the CS artillery and heavily reinforced his right flank with infantry. Jackson brought up the rest of his artillery and a duel ensued with the Union guns on Bower’s Hill. It now appeared that the Union forces were preparing to turn the Confederate left.

To counter this threat, Jackson deployed Taylor’s Louisiana brigade, reinforced by two regiments of Taliaferro’s, to the left along Abrams Creek. Taylor marched under fire to a position overlapping the Union right and then attacked Bower’s Hill. The Confederate assault swept irresistibly forward over the crest in the face of determined resistance. The Union right flank collapsed, even as the left flank was being pressured by Ewell. Union soldiers began streaming back into town.

Phase Four. US Retreat: With the collapse of both flanks, Union forces retreated through the streets of Winchester and north on the Valley Pike. Confederate pursuit was lethargic, as the troops were exhausted from the non-stop marching of the previous week. Nevertheless, many Union prisoners fell into Confederate hands. Ashby’s cavalry was disorganized from the actions of 24 May and did not pursue until Banks had already reached the Potomac River.”

Jackson’s victory of Banks was decisive. Banks lost around 2,000 troops killed, wounded and captured compared to only 400 casualties for Jackson’s Confederate forces.

When news of Jackson’s victory at Winchester reached Washington DC, a mere 75 miles away, Lincoln commanded Union Generals and McClellan to move some of their forces east towards the Union capital to prevent it from falling to the forces of Stonewall Jackson.


Sources for the above includes: First Battle of Winchester (Virginia): Casualties and Order of Battle; First Winchester (25 May 1862); Confederates Score a Victory at First Battle of Winchester; First Battle of Winchester; The First Battle of Winchester; First Battle of Winchester, 25 May 1862;


Dave Jolly

R.L. David Jolly holds a B.S. in Wildlife Biology and an M.S. in Biology – Population Genetics. He has worked in a number of fields, giving him a broad perspective on life, business, economics and politics. He is a very conservative Christian, husband, father and grandfather who cares deeply for his Savior, family and the future of our troubled nation.

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