On Sunday, Sept. 18, Lt. Gen. Jubal Early moved a portion of his Confederate force in the Shenandoah Valley from Bunker Hill, W. Va., north to Martinsburg, and drove away Federal cavalry, but returned to Bunker Hill in the evening.
His four divisions were perilously spread out, and when Union Maj. Gen. Philip Sheridan learned this, he changed his plans and moved his Army of the Shenandoah toward Winchester, planning to strike Gen. Early’s divisions separately.
The following day, Sept. 19, Gen. Sheridan’s 40,000 troops, north and east of Winchester, hit Gen. Early’s separated force of about 12,000 soldiers. During the day’s severe fighting, Maj. Gen. Robert Rodes was mortally wounded, after Gen. Early brought his entire force together. The Confederates struck a gap in the Union lines, but the Federals did not withdraw, and slowly threw back the Confederate attackers.
Late in the afternoon, the Federals attacked again and forced Gen. Early to call a retreat up the Valley Turnpike (today U.S. 211) toward Strasburg. Union casualties in the Third Battle of Winchester were heavy: over 4,000 killed, wounded and missing. Gen. Early’s casualties numbered almost the same. The Confederates withdrew toward more a defensible position at Fisher’s Hill, south of Strasburg.
On Sept. 20, clashes between opposing forces took place at Middletown, Strasburg and Cedarville (just north of Front Royal), as Gen. Sheridan’s troops pursued the retreating Confederates. By evening, Union forces occupied the high ground just north of Strasburg while the Southerners dug in on the high ground at Fisher’s Hill, just beyond Tumbling Run.
The next day, Gen. Sheridan was assigned to the permanent command of the Middle Military District, which included the Shenandoah Valley. Union cavalry engaged Confederate cavalry at Front Royal when the Southerners tried to prevent the Federal troopers from occupying the Valley between Front Royal and Luray.
On the afternoon of Sept. 22, Maj. Gen. George Crook, commanding a Union division in Gen. Sheridan’s army, attacked Gen. Early’s troops on Fisher’s Hill, and seized the Confederates in their entrenchments on the flank and rear of their positions. Two other Union divisions then attacked across Tumbling Run and up Fisher’s Hill.
During the attempted repulse of the Union attack, “Sandie” Pendleton, who had served so well on Lt. Gen. Thomas “Stonewall” Jackson’s staff, was mortally wounded. Gen. Early’s troops were routed and chased south up the Valley toward New Market, and the battle ended. Gen. Sheridan’s forces suffered a little more than 500 casualties, while Gen. Early’s losses exceeded 1,200, with almost 1,000 men missing or captured.
To cover Gen. Early’s line of retreat in the event he might want to cross the Massanutten Mountain at New Market, Confederate cavalry and artillery under command of Brig. Gen. Williams Wickham fortified the high ground at Milford (now Overall) on the Page County side of Overall Run, on the Warren-Page county line.
At about 11 a.m. that same Sept. 22, Union cavalry and artillery coming south in the Luray Valley to block Gen. Early’s retreat encountered the Confederate forces at Milford. For several hours the two sides were heavily engaged in an artillery duel while dismounted cavalry on both sides fought it out. At one point, two Federal dismounted cavalry regiments executed a flank march in an effort to reach and overwhelm the Confederate right flank; this was stopped and pushed back in a hail of Confederate fire from rifle pits at the base of the high ground.
Realizing the defenses and strength of the Confederate positions, Union Maj. Gen. Alfred Torbert ordered his troops to withdraw down the Valley toward Front Royal. Seeing the Union withdraw, the Confederates abandoned their positions at Milford and headed up the Valley to Luray, with the intent to swing west and protect the New Market Gap for Gen. Early’s line of retreat should it be needed.
This movement resulted in a brief — but sharp — fight on the northern edge of Luray on Saturday, Sept. 24, when the Union cavalry rapidly moved south from Front Royal in an attempt to stop the Confederate cavalry from reaching Luray.