Fresh from his overwhelming victory at Front Royal, Maj. Gen. Thomas J. “Stonewall” Jackson ordered his largely unscathed 16,000-man Army of the Valley on Saturday, May 24, to move quickly northwest and prevent the 8,000 Federals under Maj. Gen. Nathaniel Banks from reaching the strategic town of Winchester. After Col. Kenly and his force had been defeated at Front Royal, Gen. Banks realized his right flank at Strasburg was exposed, and he sought the defensible environs of Winchester to protect his command. Gen. Jackson divided his force and moved over several roads and reached Gen. Banks’ troops on the Valley Turnpike at Middletown and Newtown. Although the Confederate forces assailed the withdrawing Union columns along the Valley Pike, most of the Union troops escaped to enter Winchester.
Also on May 24, President Lincoln conferred with Secretary of War Stanton, and ordered Maj. Gen. John Fremont in western Virginia to advance into the Shenandoah Valley to cut off any Jackson retreat. To Maj. Gen. Irwin McDowell at Fredericksburg: “Your object will be to capture the force of Jackson and Ewell.” Gen. McDowell was instructed to take his 20,000-man command to lay aside his movement to support Gen. McClellan at Richmond and go to the Shenandoah. Diversion of McDowell’s troops gave McClellan another excuse to blame the administration for his delays and failures on the Peninsula, and to say he was undermanned despite having more than 100,000 men.
Gen. Banks on May 25 attempted to reorganize his troops and defend Winchester. Maj. Gen. Richard Ewell’s Confederate troops converged on Winchester from the southeast, using the Front Royal Pike. At Camp Hill, the Louisiana Brigade of Gen. Jackson’s division outflanked and overran the Union position on Bowers Hill. Panic immediately spread through the Federal ranks and most of Banks’ command fled through Winchester, heading north towards Harpers Ferry. A Federal soldier wrote that the battle at Winchester was “hell, or at least about as good an imitation as is often produced in the ‘upper world.’ ” Between the huge amount of supplies captured from the Federals at Front Royal and at Winchester, Gen. Banks was becoming known as “Commissary Banks” for what his troops had abandoned to the advancing Confederates.
Gen. Jackson’s troops occupied Winchester on May 26. The same day, the Confederates extended the Trans-Mississippi Department to include Arkansas, the Indian Territory (now Oklahoma), Missouri, west Louisiana and Texas. Generals Fremont and McDowell marched on May 27 to intercept Jackson’s line of retreat from Winchester after he failed to aggressively pursue Gen. Banks’ command towards Harpers Ferry. Gen. Banks’ men were now safely across the Potomac River at Williamsport, Md. Near Richmond, Gen. McClellan’s army skirmished in minor actions with Gen. Johnston’s army but still failed to take any action along the Chickahominy River.
On May 28, President Jefferson Davis wrote to Mrs. Davis: “We are steadily developing for a great battle here; under God’s favor, I trust for a decisive victory.” He was disappointed that a planned Richmond offensive by Gen. Johnston had not been launched. The next day, behind Gen. Jackson’s command, the Federals mustered 15,000 troops under Gen. Fremont; 20,000 troops under Gen. McDowell; and about 5,000 under Gen. Banks north of the Potomac River. The plan was to squeeze Jackson’s 17,000-strong Valley Army between them.
During the night, Gen. Beauregard saw that there was no hope against Gen. Halleck’s huge Federal army near Corinth, Miss., and gave orders to withdraw and move towards Tupelo. To give the impression of reinforcements, Gen. Beauregard ordered trains and troops to make loud noises in an effort to fool the waiting Federals.
The Confederates evacuated Corinth on Friday, May 30. The immense Federal army of Gen. Halleck a few miles to the north was oblivious to what Gen. Beauregard was doing in evacuating the important rail center at Corinth. In the Valley of the Shenandoah, Federals under Brig. Gen. James Shields reached Front Royal, where there was some minor skirmishing with Jackson’s command falling back from near Harpers Ferry to avoid the trap being set by converging Federal forces. Heavy rains fell on the Peninsula around Richmond as a showdown loomed between the armies of Gen. McClellan and Gen. Johnston.