On the evening of the 21st Ashby reported to Jackson that the enemy was retreating, and information came to hand that a long train of waggons, containing the baggage of 12,000 men, had left Winchester for Castleman’s Ferry on the Shenandoah.  Further reports indicated that Banks’ whole force was moving eastward, and Jackson, in accordance with his instructions to hold the enemy in the Valley, at once pushed northward.* (* A large portion of the Army of the Potomac, awaiting embarkation, still remained at Centreville.  The cavalry had pushed forward towards the Rapidan, and the Confederates, unable to get information, did not suspect that McClellan was moving to the Peninsula until March 25.)

March 22.

On the 22nd, Ashby, with 280 troopers and 3 horse-artillery guns, struck Shields’ pickets about a mile south of Winchester.  A skirmish ensued, and the presence of infantry, a battery, and some cavalry, was ascertained.  Shields, who was wounded during the engagement by a shell, handled his troops ably.  His whole division was in the near neighbourhood, but carefully concealed, and Ashby reported to Jackson that only four regiments of infantry, besides the guns and cavalry, remained at Winchester.  Information obtained from the townspeople within the Federal lines confirmed the accuracy of his estimate.  The enemy’s main body, he was told, had already marched, and the troops which had opposed him were under orders to move to Harper’s Ferry the next morning.

March 23.

On receipt of this intelligence Jackson hurried forward from his camp near Woodstock, and that night reached Strasburg.  At dawn on the 23rd four companies were despatched to reinforce Ashby; and under cover of this advanced guard the whole force followed in the direction of Kernstown, a tiny village, near which the Federal outposts were established.  At one o’clock the three brigades, wearied by a march of fourteen miles succeeding one of twenty-two on the previous day, arrived upon the field of action.  The ranks, however, were sadly weakened, for many of the men had succumbed to their unusual exertions.  Ashby still confronted the enemy; but the Federals had developed a brigade of infantry, supported by two batteries and several squadrons, and the Confederate cavalry were slowly giving ground.  On reaching the field Jackson ordered the troops to bivouac.  “Though it was very desirable,” he wrote, “to prevent the enemy from leaving the Valley, yet I deemed it best not to attack until morning.”  An inspection of the ground, however, convinced him that delay was impracticable.  “Ascertaining,” he continued, “that the Federals had a position from which our forces could be seen, I concluded that it would be dangerous to postpone the attack until next day, as reinforcements might be brought up during the night."* (* O.R. volume 12 part 1 page 381.  The staff appears to have been at fault.  It was certainly of the first importance, whether battle was intended or not, to select a halting-place concealed from the enemy’s observation.) Ashby was directed to detach half his cavalry* (* 140 sabres.) under Major Funsten in order to cover the left flank; and Jackson, ascertaining that his men were in good spirits at the prospect of meeting the enemy, made his preparations for fighting his first battle.