WINCHESTER, Military Operations at and Near. Winchester was an important strategic point during the Civil War, and it is stated on good local authority that it was occupied or abandoned 68 times by the troops of both armies. It was held by the Con federates until 11 March 1862 when Gen. J. E. Johnston having retreated from Centreville and Manassas, Gm. •Stonewall' Jackson, under Johnston's orders, withdrew from the place and retired up the Shenandoah Valley. and the Union troops, under General Banks, occupied it on the 12th. General Shields, who had followed Jackson up the valley, with a division of Banks' command, fell tack to Winchester and Jackson followed him as far as Kernstown (q.v.). four miles south of \\ inchester. where Shields at tacked and defeated him on 23 March; Jackson again retreating up the valley, Banks following and finally taking up a fortified position at Strasburg. Jackson flanked Banks out of Strasburg by moving through Luray Valley and defeating Colonel Kenly at Front Royal (q.v.) 23 May, and Banks retreated to Win chester closely pursued hr Jackson.
Winchester, First Battle of.— Banks ar rived in Winchester late on the 24th with about 8,000 men and 16 guns. Colonel Donnelly's small brigade was put in position to cover the Front Royal and Millwood roads, and was sup ported by eight guns, judiciously placed on ris ing ground_ Colonel Gordon's brigade. on the right, held a low ridge running from the town and west of the \ alley turnpike, a little over half a mile from the suburbs. Its left rested on the turnpike and its right ex tended westward along the ascending ridge in front of Winchester. Skirmishers were thrown cut in advance and guns were placed on either flank. Five companies of Michigan cavalry were held in reserve under cover of the ridge. Between Gordon and Donnelly was an interval of nearly a mile, which was filled by the princi pal part of General Hatch's cavalry brigade and two guns. The line formed the arc of a circle, covering Winchester from the west around by the south to the east. Jackson confronted this position with 16,000 men and 48 guns. and with the main body lay close to Gordon, while Ewell, with two brigades which had marched directly from Cedarville on Winchester, bivouacked opposite Donnelly's position. Jack son's plan was to hold Gordon fast, throw Ewell upon Donnelly, and then move his main body around Gordon's right, and he expected to advance upon a disorganized and demoralized army. At dawn of the 25th Ewell advanced the 21st North Carolina and opened with his artillery, whose shells fell among Donnelly's men, as they were preparing coffee and brought them to as they saw the Carolinians ad vancing in line across an open field upon the centre of the position crossing the Front Royal road_ The North Carolina men met a severe front and flank fire from the stone fences, and as they fell back Captain Best's guns threw canister into their disordered ranks and they left the held with a loss of 80 officers and men, including the two held officers with them_ A Confederate officer says. 'The slaughter was appalling and the survi4ors lied to the rear in the utmost confusion,' Ewell now up two batteries, and an artillery duel which soon ceased as a heavy fog <.ettlee1 the field Ewe II then made an at tempt to turn 1/, tinell.'s right and then en dea4ori d to turn his left and .„-ain the Mart1n4 1,urg root in 1,14 reit.. The .ittrmpt was checked. Dow, •-rne ' ut at this mo ment he re( clued order to retreat, at. Gordon had been ins r m ar.d was in re treat through NVinchester. Donnelly moved his three regiments and guns from the field in per fect order, under a heavy fire of shot and shell. and continued his retreat, keeping to the right of the Martinsburg road He had made a suc cessful resistance of over four hours against double his number, with trifling loss.
Jackson attacked Gordon's small brigade with six brigades, his attack beginning at daybreak, and being several times repulsed. Finally be got artillery in position and opened on Gordon's front and gradually worked his infantry toward the left Then he moved two brigades around Gordon's right Gordon detected the movement while it was in progress and changed position to meet it, pouring a destructive fire of musketry into the Confederate ranks, making great gaps in the line, without checking its advance: the gaps were closed and with almost perfect align ment the two brigades came on and flanking Gordon's two right regiments drove them back in some disorder. The five companies of Mich igan cavalry were now brought up and as quickly swept away. At this juncture Jackson ordered forward his entire line of six brigades and Gordon ordered a retreat through \\ in Chester, which was conducted in a manner to command Jackson's admiration_ There was some confusion in the streets of the town, but once clear of it, Hatch's cavalry and the artillery covered the withdrawal, until the infantry was well on the Martinsburg pike. Jackson with his main body pursued five miles beyond 1% in chester and Banks continued his retreat to the Potomac, crossing it at Williamsport on the 26th. Banks' loss May 23-25, including Front Royal and the retreat from Strasburg to the Potomac, was 62 killed. 243 wounded and 1.714 missing. Jackson's loss was OS killed, 329 wounded and three missing. Jackson remained at and in the vicinity of Winchester until 31 May, when, his rear being threatened by the converging columns of Fremont from the west and McDowell from the east, be retreated up the valley and the Union troops reoccupied Consult 'Official Records' XII); Allan, 'Jackson's Valley Campaign.'
During Lee's campaign against Pope the town was occupied by Gen. Julius White with a brigade of over 2,000 men. On the night of 2 Sept 1S412 White, under General Halk-ck's order, spiked four heavy siege guns in the works and withdrew to Harper's Ferry ; the Confederates occupying the place next day. The Confederates held the place in small force until 3 December, when, upon the advance of a column from Harpers Ferry, under General Geary, they retired, and Geary occupied the town next day. Geary soon withdrew and the reoccupied and held the town until near the end of December, when it was again taken by Union troops under General Milroy. Milroy fortified the place and occupied also Berry s ille and Romney, with outposts toward Strasburg and Front Royal. Harper's Ferry, Martinsbur.z. Williamsport and posts westward to Cumberland and New Creek were held by Union troop, belonging to Gen. B. F. Kelley's Winchester, Second Battle %%In General Lee began his preparations for the second invasion of Maryland, which culminated in the battle of Gettysburg, he turned hi, thoughts to the clearing of the Shenandoah Valley. At this time Winchester was held by General Milroy, with the two brigades of Gen. W L Elliott and Colonel Ely, numbering about 7.(01) effective men. Colonel McReynolds' brigade of 1,800 men was at Berryville. The main works defending Winchester were on a ridge north of the town and consisted of two forts known as the •main fort' and the *Star fort.' mounting four 20-pounder Parrotts and two 24-pounder howitzers. Surrounding these were smaller works connected by rifle-pits. The expressed object in holding the place was to observe and hold in check the enemy in the valley, and to secure the Baltimore and Ohio Railroad against depredations. Milroy was ex pressly instructed to undertake no offensive operations in force. On 7 June General Lee be gan his operations in the valley by ordering General Imboden, in the upper valley, to make a demonstration with his cavalry brigade on Romney in order to cover the movement against Winchester and prevent the Union troops at that place from being reinforced by Kelley's troops on the line of the Baltimore and Ohio Rail road. General Jenkins' cavalry brigade was ordered to join Ewell's infantry corps near Front Royal. Both Imboden and Jenkins were in position by the 10th, and on that day Ewell set out from near Culpeper Court House for Winchester by way of Gaines' Cross Roads, Chester Gap and Front Royal, to Cedarville, which was reached on the 12th. Here, next day, Ewell detached Rodes' division and Jenkins' cavalry brigade to move on Berryville and en deavor to capture McReynolds' brigade, hut, warned by Milroy, McReynolds made good his retirement, with small los,joined Milroy at %%inchester on the night of the 13th, and was assigned to the Star tort, immediately north of the main work. On the same day Early's divi sion marched on Winchester by Newtown and the Valley pike, while Edward Johnson's divi sion moved upon the town by the direct road from Front Royal. The two divisions, driving in Milroy's outposts, were in position before Winchester on the evening of the 13th. For some days Milroy had felt the pressure from Confederate cavalry, but had no idea that Lee was threatening the valley until a prisoner taken in a skirmish on the Strasburg road, on the evening of the 13th, informed him that he was confronted by Ewell's corps and that Longstreet's was near. Fully recognizing the fact that an orderly withdrawal was imprac ticable, he resolved to act on the defensive, and, ii not relined, force his way through what might appear the weakest part of his lines. At night of the 13th Ewell ordered Early to attack the works on the north and west of the town next morning, while, as a diversion, John son demonstrated against the east and south east. In the forenoon Johnson made his attack on the eastern side of the town, between the Millwood and Berryville roads, held by Colonel Ely's brigade, and was repulsed by the Eighth and 87th PennssIvania, which charged John son's retreating troops, but were speedily drisen Lack by fresh troops, and after some sharp fighting Johnson gained part of the town, but was quickly shelled out and made no further effort West of the ridge on n hich the main forts were thrown up, and about 1,300 yards distant, is another parallel ridge, called Flint Ridge, where an isolated earthwork of slight strength had been thrown up to command the Pughtown and Romney roads. Tt was held by the 110th Ohio, a company of the 116th, and a reg ular battery, commanded by Lieutentant Wallace F. Randolph , all under command of Col. J. W. Keifer. Early, leaving Gordon's brigade south of the town to engage Milroy's attention, moved with the remainder of his division to the left and west, then north, crossed the Romney road, and about 5 having gained Round Moun tain, south of the Pughtown road, and put 20 guns in position, without being perceived, opened an unexpected fire on Keifer's work aM soon silenced Randolph's battery, upon which Hays' brigade, in two lines, made a quick dash, and after a stubborn resistance carried the work, and captured the battery of six guns. Keifer, with a loss of over 40 men, withdrew under cover of the fire from the guns of the main works. This was followed by an artillery duel which was kept up until 8 rte. during which Milroy withdrew his detachments to his main works. Darkness ended the contest.