Up to the present his operations had been perfectly successful. He had captured over 700 of the enemy, with a loss of only 40 or 50 to himself. He had seized stores to the value of three hundred thousand dollars (60,000 pounds), and a large quantity had been burned by the enemy. He had turned the intrenched position at Strasburg. He threatened the Federal line of retreat. Banks was completely at his mercy, and there seemed every prospect of inflicting on that ill-starred commander a defeat so decisive as to spread panic in the council chambers of the Northern capital.
But the problem was not so simple as it seemed. In the first place, although the positions of the Federals had been thoroughly examined, both by staff officers and scouts, the information as to their numbers was somewhat vague. Banks had actually about 8000 effectives at Strasburg; but so far as the Confederates knew it was quite possible that he had from 12,000 to 15,000. There is nothing more difficult in war than to get an accurate estimate of the enemy’s numbers, especially when civilians, ignorant of military affairs, are the chief sources of information. The agents on whom Jackson depended for intelligence from within the enemy’s lines were not always selected because of their military knowledge. “On the march to Front Royal,” says General Taylor, “we reached a wood extending from the mountain to the river, when a mounted officer from the rear called Jackson’s attention, who rode back with him. A moment later there rushed out of the wood a young, rather well-looking woman, afterwards widely known as Belle Boyd. Breathless with speed and agitation, some time elapsed before she found her voice. Then, with much volubility, she said we were near Front Royal; that the town was filled with Federals, whose camp was on the west side of the river, where they had guns in position to cover the bridge; that they believed Jackson to be west of the Massanuttons, near Harrisonburg; that General Banks was at Winchester, where he was concentrating his widely scattered forces to meet Jackson’s advance, which was expected some days later. All this she told with the precision of a staff officer making a report, and it was true to the letter. Jackson was possessed of this information before he left New Market, and based his movements on it; but it was news to me.”
In the second place, Banks had still the means of escape. He could hardly prevent the Confederates from seizing Winchester, but he might at least save his army from annihilation. Jackson’s men were exhausted and the horses jaded. Since the morning of the 19th the whole army had marched over eighty, and Ewell’s division over ninety miles. And this average of seventeen miles a day had been maintained on rough and muddy roads, crossed by many unbridged streams, and over a high mountain. The day which had just passed had been especially severe. Ewell, who was in bivouac at Cedarville, five miles north of Front Royal on the Winchester turnpike, had marched more than twenty miles; and Jackson’s own division, which had made four-and-twenty, was on foot from five in the morning till nine at night.
Banks’ natural line of retreat led through Winchester, and the Confederate advanced guard at Cedarville was two miles nearer that town than were the Federals at Strasburg. But it was still possible that Banks, warned by Kenly’s overthrow, might withdraw by night; and even if he deferred retreat until daylight he might, instead of falling back on Winchester, strike boldly for Front Royal and escape by Manassas Gap. Or, lastly, he might remain at Strasburg, at which point he was in communication, although by a long and circuitous road, with Frémont at Franklin.
Jackson had therefore three contingencies to provide against, and during the night which followed the capture of Front Royal he evolved a plan which promised to meet them all. Ashby, at daybreak, was to move with the 7th Virginia cavalry in the direction of Strasburg; and at the same hour a staff officer, with a small escort, supported by Taylor’s Louisianians, was to ride towards Middletown, a village five miles north of Strasburg and thirteen from Winchester, and to report frequently. The 2nd and 6th Virginia cavalry, under General Steuart, were to advance to Newtown, also on the Valley turnpike, and eight miles from Winchester; while Ewell, with Trimble’s brigade and his artillery, was to move to Nineveh, two miles north of Cedarville, and there halt, awaiting orders. The remainder of the command was to concentrate at Cedarville, preparatory to marching on Middletown; and strong cavalry patrols were to keep close watch on the Strasburg to Front Royal road.[[17]]
6 a.m. From Cedarville to Middletown is no more than seven miles, and Taylor’s brigade is reported to have moved at six a.m., while Ashby had presumably already marched. But notwithstanding the fact that Banks’ infantry did not leave Strasburg till ten a.m., and that it had five miles to cover before reaching Middletown, when the Confederates reached the turnpike at that village the Federal main body had already passed, and only the rear-guard was encountered.
It seems evident, therefore, that it was not till near noon that Jackson’s patrols came in sight of Middletown, and that the Confederate advanced guard had taken at least six hours to cover seven miles. The country, however, between Cedarville and the Valley turnpike was almost a continuous forest; and wood-fighting is very slow fighting. The advance had met with strong resistance. General Gordon had prudently sent the 29th Pennsylvania to Middletown at an early hour, with orders to reconnoitre towards Front Royal, and to cover Middletown until the army had passed through.
7 a.m. Supported by a section of artillery, the regiment had moved eastward till it struck the Confederate scouts some four miles out on the Cedarville road. After a long skirmish it was withdrawn to Middletown; but the 1st Maine cavalry, and a squadron of the 1st Vermont, about 400 strong, which had been ordered by Banks to proceed in the same direction, made a vigorous demonstration, and then fell back slowly before the advanced guard, showing a bold front, using their carbines freely, and taking advantage of the woods to impose upon the enemy.
10.15 a.m. These manœuvres succeeded in holding the Confederates in check till after ten o’clock, for the heavy timber concealed the real strength of the Federals, and although Ashby, with the 7th Virginia, had marched to the scene of action, the infantry was not yet up. It is to be remembered that at daybreak the Valley army was by no means concentrated. Jackson had with him at Cedarville only Ewell’s division, his own division having halted near Front Royal. This last division, it appears from the reports, did not leave Front Royal until 8 a.m.; a sufficiently early hour, considering the condition of the men and horses, the absence of the trains, and the fact that one of the brigades had bivouacked four miles south of the village.[[18]] It was not, then, till between nine and ten that the column cleared Cedarville, and Middletown was distant nearly three hours’ march, by an exceedingly bad road.
In all probability, if Jackson, at daybreak or soon afterwards, had marched boldly on Middletown with Ewell’s division, he would have been able to hold Banks on the Valley turnpike until the rest of his infantry and artillery arrived. But he had always to bear in mind that the Federals, finding their retreat on Winchester compromised, might make a dash for Manassas Gap. Now the road from Strasburg to Manassas Gap was protected throughout its length by the North Fork of the Shenandoah; and to attack the Federals on the march, should they take this road, the Confederates would have to move through Cedarville on Front Royal. This was the only road by which they could reach the river, and the bridges at Front Royal were the only available points of passage. Jackson, it appears, was therefore reluctant to leave Cedarville, within easy reach of the bridges, until he received information of his enemy’s designs, and that information, which had to be sought at a distance, was naturally long in coming.