Entertainment to the Utmost of Our Aspirations

Major General Thomas J. “Stonewall” Jackson’s Confederate Army of the Shenandoah was stationed at Winchester, guarding Virginia’s Shenandoah Valley against a Federal invasion from the north. Jackson’s force consisted of just 3,600 infantry, 600 cavalry, and 27 cannon in six batteries.

Jackson’s main threat had come from Federals under Brigadier General Frederick Lander. Lander had refused to surrender Hancock to Jackson in January, and he reluctantly obeyed orders to abandon Romney. His men were now camped at Paw Paw, and Lander was critically ill with pneumonia. He received orders to advance to Martinsburg on March 1, but he collapsed and died the following evening. His aide, Captain Simon F. Barstow, reported, “General Lander has just died without suffering. This campaign has killed him, for he held on in spite of failing health and strength to the last.” Lander was replaced by Colonel Nathan Kimball.

Kimball’s Federals belonged to the Department of the Shenandoah, commanded by Major General Nathaniel P. Banks. Banks had been ordered to move his main force across the Potomac River and occupy key points in the Valley as part of an effort to keep Jackson from moving east and reinforcing the Confederate Army of the Potomac. Banks sent 38,000 men across and quickly occupied such places as Harpers Ferry, Bolivar Heights, Charlestown, and Martinsburg, among others. Soon the Federals were just 20 miles up the Valley Turnpike from Jackson’s small force.

Though the Federals were closing in with superior numbers, Jackson remained defiant. His aide Sandie Pendleton wrote his mother, “That Winchester will be left, I doubt not, for it ought, but I am equally certain this part of the state is not to be abandoned, and that General Jackson will not leave without fighting. When or where this fighting is to take place I know no more than you.”

Federals reconnoitered the area between Harpers Ferry and Winchester, and reported that Winchester could be easily taken. When a local Unionist informed Banks that Jackson intended to abandon the town, Banks asked his superior, Major General George B. McClellan, for permission to advance. Banks assured him, “Our troops are in good health and spirits, eager for work.” McClellan did not respond, so Banks made no immediate moves.

General Joseph E. Johnston, commanding the Confederate Army of the Potomac at Centreville, Virginia, was preparing to withdraw southward, and he instructed Jackson to do the same. Jackson was to delay Banks as much as possible by guarding the mountain passes to ensure that Banks would not turn east and attack Johnston’s flank. Jackson believed that the best way to delay Banks was to hold Winchester, so, unaware that he was outnumbered eight-to-one, he resolved to make a stand.

Maj Gen “Stonewall” Jackson | Image Credit: SonoftheSouth.net

Jackson wrote Johnston on the 8th, “I greatly desire to hold this place so far as may be consistent with your views and plans, and am making arrangements, by constructing works, removing forests, etc., to make a stand.” Johnston had ordered Brigadier General D.H. Hill’s Confederates to fall back from Leesburg, so Jackson asked, “And now, General, that Hill has fallen back, can you not send him over here? The very idea of reinforcements coming to Winchester would, I think, be a damper to the enemy, in addition to the fine effect that would be produced on our own troops.” It would also ensure that “a kind Providence may enable us to inflict a terrible wound.”

After two days passed, Johnston had not responded to Jackson’s request and the Federals were on the verge of surrounding Winchester. Banks had about 18,000 men ready to move into the town, with another 12,000 within striking distance. Jackson reluctantly directed that his army supply train and heavy guns be moved to the south side of Winchester in preparation to evacuate.

The next day, Jackson decided that he would surprise Banks with a rare night attack. He held a council of war to discuss the plan, but he was told that the supply trains had been moved five miles south of Winchester, and the infantry had followed them. This made the attack impossible. Dismayed, Jackson finally issued orders to evacuate the town. He angrily told his surgeon, Dr. Hunter Maguire, “That is the last council of war I will ever hold!”

The Confederates pulled out of Winchester on the morning of the 12th, saddened to be leaving their families and homes behind. They marched south on the Valley Turnpike and made camp between Cedar Creek and Strasburg. The site lacked drinkable water, and sickness ran rampant among the men. Banks’s Federals entered Winchester that same day, where few residents greeted them. Some Federal officers grumbled about missing a chance to destroy Jackson, but Colonel George H. Gordon of the 2nd Massachusetts assured them that “this chieftain (Jackson) would be apt, before the war closed, to give us an entertainment up to the utmost of our aspirations.”

Jackson fell back to Strasburg, where he gathered supplies and recruits. Word soon came that Banks had sent a division of 9,500 Federals under Brigadier General James Shields to confront the Confederates. Unwilling to engage the Federals just yet, Jackson resumed his withdrawal on the 15th, passing scores of weeping civilians and arriving at Mount Jackson the next day. This placed Jackson’s men near a mountain pass so they could move east and reinforce Johnston if needed, or prevent Banks from going east himself.

Meanwhile, Major General George B. McClellan was preparing to move his Federal Army of the Potomac down the Virginia coast to launch his Peninsula campaign. McClellan was required to leave an adequate force behind to protect Washington, which was Banks’s force, now designated the Fifth Corps of McClellan’s army. Banks had two divisions in the Shenandoah Valley, but now he was obliged to send one east to occupy the Centreville-Manassas line that Johnston’s Confederates had abandoned. This prompted Banks to halt Shields’s advance at Strasburg.

Jackson responded by sending Colonel Turner Ashby’s 700 troopers to harass Shields’s Federals now between Strasburg and Winchester. Skirmishing occurred at multiple points, highlighted by an engagement on the 19th in which Ashby’s men fought a force 10 times their size with such ferocity that the Federals thought they were facing “Jackson’s whole force.” The troopers seemed to appear out of nowhere, attacking from various angles with support from just two or three guns. Ashby soon gained a reputation as “the terror and the wizard of the Shenandoah.”

Shields disengaged, and Ashby reported that the Federals were falling back to Winchester. Once they reached the town, Shields met with his commanders and happily announced, “Jackson was off a long distance and that all we would have to do, until we had got things in readiness for an advance, would be to picket well in front.”

Shields’s withdrawal led Johnston to conclude that McClellan was pulling Federals from the Valley to bolster his Peninsula campaign. Johnston wrote Jackson, “Would not your presence with your troops nearer Winchester prevent the enemy from diminishing his force there? It is important to keep that army in the Valley, and that it should not reinforce McClellan. Do try to prevent it by getting and keeping as near as prudence will permit.” Jackson quickly responded by organizing his new recruits (including noted engineer and cartographer Jedediah Hotchkiss) and planning to pursue Shields northward.

But first Jackson had to address a problem in which men who had been drafted into his ranks were refusing to fight. These were mainly area pacifists such as Quakers and Mennonites who objected to war of any kind. To attain “the highest degree of efficiency” and encourage “loyal feelings and co-operation,” Jackson employed these men in non-combatant roles such as teamsters and cooks. This would “not only enable many volunteers to return to the ranks, but will also save many valuable horses and other public property in addition to arms.”

March 22 dawned wet and cold as Jackson’s Confederates moved out of Mount Jackson on what would become a legendary campaign. They covered 26 miles and arrived at Strasburg that night. Meanwhile, Ashby’s troopers clashed with Federals outside Kernstown, a few miles south of Winchester. The Confederates held off an entire brigade, wounding Shields in the process, before finally falling back to Strasburg.

Both Shields and Banks thought the skirmish to be nothing more than a scouting expedition. Banks prepared to go to Manassas, and Shields fell back to Winchester. He made no arrangements for defense. Ashby returned to Jackson’s command and erroneously reported that most of Shields’s division had fallen back to Harpers Ferry, leaving just 4,000 in the Winchester area (Shields actually had closer to 9,000 men, or over double Jackson’s number). Jackson, determined to give battle before the Federals could leave the Valley, planned to attack the next day. Banks, who returned to Washington with his other division, refused to believe that Jackson would try it.


  • Clark, Champ, Decoying the Yanks: Jackson’s Valley Campaign. Alexandria, VA: Time-Life Books, 1983.
  • Cozzens, Peter, Shenandoah 1862: Stonewall Jackson’s Valley Campaign. The University of North Carolina Press (Kindle Edition), 2008.
  • Foote, Shelby, The Civil War, A Narrative: Fort Sumter to Perryville. New York: Vintage Books, 1958.
  • Johnston, Joseph E., Narrative of Military Operations During the Civil War. Sharpe Books, Kindle Edition, 2014.
  • Klein, Frederic S. (Patricia L. Faust ed.), Historical Times Illustrated Encyclopedia of the Civil War. New York: Harper & Row, 1986.
  • Long, E.B. with Long, Barbara, The Civil War Day by Day. New York: Da Capo Press, Inc., 1971.
  • United States War Department, War of the Rebellion: A Compilation of the Official Records of the Union and Confederate Armies. Series 1 – Vol. 12. Washington, D.C.: GPO, 1880-1902.

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