On leaving Winchester, Williams’ division had struck due east, passing through the village of Berryville, and making for Snicker’s Gap in the Blue Ridge. The Berryville road had thus become of importance to the garrison of Winchester, for it was from that direction, if they should become necessary, that reinforcements would arrive. General Kimball, commanding in Shields’ absence the division which confronted Ashby, had therefore posted the larger portion of his troops eastward of the pike. A strong force of infantry, with waving colours, was plainly visible to the Confederates, and it was seen that the extreme left was protected by several guns. On the right of the road was a line of skirmishers, deployed along the base of Pritchard’s Hill, and on the knoll itself stood two batteries. The wooded ridge to westward was as yet unoccupied, except by scouting parties.
Jackson at once determined to turn the enemy’s right. An attack upon the Federal left would have to be pushed across the open fields and decided by fair fighting, gun and rifle against gun and rifle, and on that flank the enemy was prepared for battle. Could he seize the wooded ridge on his left, the initiative would be his. His opponent would be compelled to conform to his movements. The advantages of a carefully selected position would be lost. Instead of receiving attack where he stood, the Federal general would have to change front to meet it, to execute movements which he had possibly not foreseen, to fight on ground with which he was unfamiliar; and, instead of carrying out a plan which had been previously thought out, to conceive a new one on the spur of the moment, and to issue immediate orders for a difficult operation. Hesitation and confusion might ensue; and in place of a strongly established line, confidently awaiting the advance, isolated regiments, in all the haste and excitement of rapid movement, or hurriedly posted in unfavourable positions, would probably oppose the Confederate onset. Such are the advantages which accrue to the force which delivers an attack where it is not expected; and, to all appearance, Jackson’s plan of battle promised to bring them into play to the very fullest extent. The whole force of the enemy, as reported by Ashby, was before him, plainly visible. To seize the wooded ridge, while the cavalry held the Federals fast in front; to pass beyond Pritchard’s Hill, and to cut the line of retreat on Winchester, seemed no difficult task. The only danger was the possibility of a counterstroke while the Confederates were executing their turning movement. But the enemy, so far as Jackson’s information went, was rapidly withdrawing from the Valley. The force confronting him was no more than a rear-guard; and it was improbable in the extreme that a mere rear-guard would involve itself in a desperate engagement. The moment its line of retreat was threatened it would probably fall back. To provide, however, against all emergencies, Colonel Burks’ brigade of three battalions was left for the present in rear of Kernstown, and here, too, remained four of the field batteries. With the remainder of his force, two brigades of infantry and a battery, Jackson moved off to his left. Two companies of the 5th Virginia were recruited from Winchester. Early in the day the general had asked the regiment for a guide familiar with the locality; and, with the soldier showing the way, the 27th Virginia, with two of Carpenter’s guns as advanced guard, struck westward by a waggon track across the meadows, while Ashby pressed the Federals in front of Kernstown.
3.45 p.m. The main body followed in two parallel columns, and the line of march soon brought them within range of the commanding batteries on Pritchard’s Hill.[[18]] At a range of little more than a mile the enemy’s gunners poured a heavy fire on the serried ranks, and Carpenter, unlimbering near the Opequon Church, sought to distract their aim.
The Confederate infantry, about 2,000 all told, although moving in mass, and delayed by fences and marshy ground, passed unscathed under the storm of shell, and in twenty minutes the advanced guard had seized the wooded ridge.
Finding a rocky clearing on the crest, about a mile distant from Pritchard’s Hill, Jackson sent back for the artillery. Three batteries, escorted by two of Burke’s battalions, the 21st Virginia and the Irishmen, pushed across the level as rapidly as the wearied teams could move. Two guns were dismounted by the Federal fire; but, coming into action on the ridge, the remainder engaged the hostile batteries with effect. Meanwhile, breaking their way through the ragged undergrowth of the bare March woods, the infantry, in two lines, was pressing forward along the ridge. On the right was the 27th Virginia, supported by the 21st; on the left, Fulkerson’s two battalions, with the Stonewall Brigade in second line. The 5th Virginia remained at the foot of the ridge near Macauley’s cottage, in order to connect with Ashby. Jackson’s tactics appeared to be succeeding perfectly. A body of cavalry and infantry, posted behind Pritchard’s Hill, was seen to be withdrawing, and the fire of the Federal guns was visibly weakening.
4.30 p.m. Suddenly, in the woods northward of the Confederate batteries, was heard a roar of musketry, and the 27th Virginia came reeling back before the onslaught of superior numbers. But the 21st was hurried to their assistance; the broken ranks rallied from their surprise; and a long line of Federal skirmishers, thronging through the thickets, was twice repulsed by the Southern marksmen.[[19]]
Fulkerson, further to the left, was more fortunate than the 27th. Before he began his advance along the ridge he had deployed his two battalions under cover, and when the musketry broke out on his right front, they were moving forward over an open field. Half-way across the field ran a stone wall or fence, and beyond the wall were seen the tossing colours and bright bayonets of a line of battle, just emerging from the woods. Then came a race for the wall, and the Confederates won. A heavy fire, at the closest range, blazed out in the face of the charging Federals, and in a few moments the stubble was strewn with dead and wounded. A Pennsylvania regiment, leaving a colour on the field, gave way in panic, and the whole of the enemy’s force retreated to the shelter of the woods. An attempt to turn Jackson’s left was then easily frustrated; and although the Federals maintained a heavy fire, Fulkerson’s men held stubbornly to the wall.
In the centre of the field the Northern riflemen were sheltered by a bank; their numbers continually increased, and here the struggle was more severe. The 4th and 33rd Virginia occupied this portion of the line, and they were without support, for the 2nd Virginia and the Irish battalion, the last available reserves upon the ridge, had been already sent forward to reinforce the right.
The right, too, was hardly pressed. The Confederate infantry had everywhere to do with superior numbers, and the artillery, in that wooded ground, could lend but small support. The batteries protected the right flank, but they could take no share in the struggle to the front; and yet, as the dusk came on, after two long hours of battle, the white colours of the Virginia regiments, fixed fast amongst the rocks, still waved defiant. The long grey line, “a ragged spray of humanity,” plied the ramrod with still fiercer energy, and pale women on the hills round Winchester listened in terror to the crashing echoes of the leafless woods. But the end could not be long delayed. Ammunition was giving out. Every company which had reached the ridge had joined the fighting line. The ranks were thinning. Many of the bravest officers were down, and the Northern regiments, standing staunchly to their work, had been strongly reinforced.
Ashby for once had been mistaken. It was no rearguard that barred the road to Winchester, but Shields’ entire division, numbering at least 9,000 men. A prisoner captured the day before had admitted that the Confederates were under the impression that Winchester had been evacuated, and that Jackson had immediately moved forward. Shields, an able officer, who had commanded a brigade in Mexico, saw his opportunity. He knew something of his opponent, and anticipating that he would be eager to attack, had ordered the greater part of his division to remain concealed. Kimball’s brigade and five batteries were sent quietly, under cover of the night, to Pritchard’s Hill. Sullivan’s brigade was posted in support, hidden from view behind a wood. The cavalry and Tyler’s brigade were held in reserve, north of the town, at a distance where they were not likely to be observed by the inhabitants. As soon as the Confederates came in sight, and Kimball deployed across the pike, Tyler was brought through the town and placed in rear of Sullivan, at a point where the road dips down between two parallel ridges. Shields himself, wounded in the skirmish of the preceding day, was not present at the action, although responsible for these dispositions, and the command had devolved on Kimball. That officer, when Jackson’s design became apparent, ordered Tyler to occupy the wooded ridge; and it was his five regiments, over 3,000 strong, which had struck so strongly at the Confederate advance. But although superior in numbers by a third, they were unable to make headway. Kimball, however, rose to the situation before it was too late. Recognising that Ashby’s weak attack was nothing more than a demonstration, he hurried nearly the whole of his own brigade, followed by three battalions of Sullivan’s, to Tyler’s aid, leaving a couple of battalions and the artillery to hold the pike.