The arrival of these reinforcements seriously embarrassed Milroy; and it will be seen hereafter that it would have been much better for all concerned if they had retreated to Harper's Ferry at once. They acted, however, strictly in obedience to orders.
Rodes' division, after the taking of Berryville, kept on towards
Martinsburg, and bivouacked at a place called Summit Point.
On the morning of the 13th Milroy had sent out a detachment under General Elliot on the Strasburg road, and another under Colonel Ely on the Front Royal road, to reconnoitre. Eliott found no enemy, and returned. An attempt was made to cut him off from the town, but it was repulsed. His troops were then massed on the south side behind Mill Creek and a mill-race which ran parallel to it, and were protected by stone fences. Colonel Ely had a brisk artillery skirmish with Ewell's advance, and then fell back to Winchester, taking post at the junction of the Front Royal and Strasburg roads. The enemy did not attempt to cross the creek that night, but at 5 P.M. they advanced and captured a picket-post which commanded the Strasburg road, but were soon driven out.
From a prisoner captured in this skirmish Milroy learned the highly important intelligence that he was confronted by Ewell's corps and that Longstreet was rapidly approaching.
The most natural course under the circumstances would have been for him to retreat at once, but McReynolds' brigade had just arrived, exhausted by their forced march, and could go no further, without some hours' rest. To move without them would be to sacrifice a large part of his force. He still cherished the hope that Hooker's army would follow Lee up closely and come to his relief.
Ewell at night directed Early's division to attack the works on the north and west of the town at daylight the next morning, while Johnson's division demonstrated against the east and southeast.
Early on Sunday, the 14th, Milroy sent out a detachment to see if the enemy had established themselves on the Pughtown or Romney roads. The party returned about 2 P.M. and reported the roads clear, but soon after the rebels came in great force from that direction, so that Milroy's hopes of escaping by the routes leading to the northwest were dissipated. Immediately west of Winchester, and parallel with Applebie Ridge, on which the main forts were situated, there is another ridge called Flint Ridge, where rifle pits had been commenced to command the Pughtown and Romney roads. These were held by one regiment, and part of another under Colonel Keifer of the 110th Ohio, together with Battery "L" of the 5th United States Artillery. Early's division made a sudden attack there, preliminary to which he opened fire with four batteries. He charged into these rifle-pits and took them, but the garrison retreated successfully, under cover of the fire, from the main works above, which were held by Elliot's and McReynolds' brigades. This was followed by an artillery duel, which was kept up until 8 P.M. without any special results.
Johnson's division at daybreak attacked the eastern side of the town, held by Colonel Ely's brigade, but was gallantly met and repulsed by the 8th Pennsylvania and 87th Pennsylvania. These two regiments, by Milroy's order, made a bold charge against the enemy as they were retiring, but the latter were so suddenly and strongly reinforced that the two regiments were glad to get back to their shelter in the fortified suburbs. They were followed up however, and after severe fighting Johnson gained possession of a part of the town. This apparent success proved of no avail, for the forts above shelled him out. He therefore retired and made no further attempt in that direction.
Darkness ended the struggle for the day. Johnson then left one brigade to prevent Milroy from escaping toward the east and went off with the remainder of his division to form across the Martinsburg pike, about three miles north of Winchester, to intercept Milroy's retreat in that direction.
While these events were going on in the Valley, Imobden's cavalry was engaged in breaking up the Baltimore and Ohio Railroad near Romney, to prevent Milroy from receiving any reinforcements from the west.