During the morning, Lieutenant General Jubal Early appeared to have a victory for his Confederate army, as he captured over 1,000 prisoners and over 20 artillery pieces while forcing seven enemy infantry divisions to fall back.

The Union army, led by Major General Philip Sheridan, rallied in late afternoon and drove away Early's men.

[10] Early then sent cavalry commanded by Brigadier General John McCausland on a northern raid in late July that resulted in the burning of the town of Chambersburg, Pennsylvania.

[25] Early believed that the addition of Kershaw's Division (2,700 fighters), Rosser's Laurel Brigade (600 men), the artillery battalion, and the return of stragglers from the September battles almost made up for his losses at Winchester and Fisher's Hill.

[63] Sheridan ordered all three divisions of cavalry to accompany him to Front Royal, intending to send them to destroy a Virginia Central Railroad bridge.

This was disinformation on Early's part, hoping that it would induce the Federals to withdraw down the Valley, but instead, Sheridan sent his cavalry back to the infantry camps along Cedar Creek.

[63][72][Note 14] Gordon persuaded Early to approve an attack on the Union left flank, and believed they could destroy Sheridan's army.

[76] Gordon's force would use the narrow mountain trail to get behind the Union left, which required an evening (October 18) departure time in order to be in position before dawn.

A small brigade of cavalry commanded by Colonel William H. F. Payne would move with Gordon with the mission of capturing Sheridan at his headquarters at the Belle Grove Plantation house near Middletown.

[77] Lomax would move via Front Royal to Newtown (later named Stephens City), where he could cut off a Union retreat down the Valley Pike.

[88] Du Pont's efforts and Wildes' two regiments were only thing (other than fog) slowing the initial Confederate thrust by Kershaw's Division.

[96][Note 19] The XIX Corps began receiving artillery fire from the south and east, and was attacked from those directions by Confederate troops, commanded by Kershaw and Evans, less than one hour after the start of the battle.

[97] XIX Corps Commander Emory received unexpected assistance from Wildes' partial brigade from Crook's Army of West Virginia.

In the confusion of battle, Wildes' two regiments had been unable to reunite with Crook and the retreating men from the Army of West Virginia—so they offered assistance to Emory and Wright.

[102] At that time, Kershaw and Evans were driving toward the camps of the Union VI Corps, and the Confederate divisions of Pegram and Ramseur were aligned along the west side of the pike north of Early and Gordon's meeting place.

[103] Early later wrote that at the time of the meeting, "...the 19th and Crook's corps were in complete rout, and their camps, with a number of pieces of artillery and a considerable quantity of small arms, abandoned.

"[104] He also noted that the position of the Union VI Corps on a ridge west of Middletown was "a strong one", and Wharton's division had been driven back.

[103] Acting Union VI Corps Commander Ricketts had his men moving to position within 20 minutes of the start of the Confederate offensive.

With no support on his right, Getty moved his division back about 300 yards (270 m) to a stronger defensive position at the town cemetery on a partially wooded hill west of Middletown.

While waiting for orders, both Merritt and Custer sent their escort companies to the Valley Pike to attempt to stop Union infantry men from fleeing toward Winchester.

Ironically, the main reason two of the Union cavalry divisions were present for the battle was Early's Longstreet ruse from a few days earlier.

[126] In a second meeting with Early, Gordon wanted to press the attack against the VI Corps immediately, and later wrote that the "fatal halting...converted the brilliant victory of the morning into disastrous defeat in the evening".

[134] On the Union left, Merritt's cavalry made two charges only to be repulsed by Confederate artillery and enfilading fire from enemy infantry that had resisted the advance of the VI Corps.

He planned to get to the rear of Early's men and secure the Valley Pike at the bridge over Cedar Creek—which would cut off the main Confederate route of retreat.

[Note 25] The fields between Cedar Creek and Fisher's Hill were filled with fleeing men, wagons, ambulances, and artillery—all being chased by Union cavalry using sabers.

[142] The situation worsened for the Confederates when a small bridge on the Valley Pike south of Strasburg collapsed, making it impossible to cross with wagons or artillery.

[147][Note 26] The highest ranking Confederate casualty was Major General Ramseur, an infantry division commander, who was mortally wounded and captured by the 1st Vermont Cavalry Regiment.

[126] Cavalry accounted for nearly half (ten of twenty-one) of the medal of honor winners at Cedar Creek, even though it had only about one fourth of the men present.

[164] Sheridan's success propelled him to status only eclipsed by Grant and William Tecumseh Sherman, and he would eventually become Commanding General of the United States Army.

[172] Belle Grove, built in the 1790s by the brother-in-law of future President James Madison, was listed in the Virginia Landmarks Register on November 5, 1968.