Despite Wright's strong feelings against the attack, Sheridan believed it was the only way to break the Valley's Gibraltar. After the war ended Sheridan failed to give Crook any credit for devising the plan to crush Early at Fisher's Hill. 'I resolved on the night of the 20th,' Sheridan penned in his memoirs, 'to use again a turning-column, against his left, as had been done' at Third Winchester. 'To this end I resolved to move Crook, unperceived if possible, over to the eastern face of Little North Mountain, whence he could strike the left and rear of the Confederate line.' Sheridan's reluctance to credit Crook for his role in the Shenandoah Valley in 1864 marred a four-decades-old friendship.

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Other officers, however, did give Crook credit. Chief among them was Hayes. Four days after the battle Hayes wrote his uncle: 'At Fisher's Hill the turning of the Rebel left was planned and executed by General Crook against the opinions of other generals….General Sheridan is a whole-souled brave man and believes in Crook, his old class and roommate at West Point. Intellectually he is not General Crook's equal, so that, as I said, General Crook is the brains of this army.' Others viewed things with a bit more objectivity. Artillery Captain Henry A. DuPont recognized that the flank attack was Crook's idea, but keenly observed that 'Hayes' admiration for his corps commander may have led him to underestimate the intellectual ability of his commanding general.'

Regardless of who should receive the lion's share of the credit for conceiving the plan, both Sheridan and Crook knew that if the plan was going to succeed, the flank attack needed to be kept secret — therefore many of Crook's movements would have to take place under cover of darkness or amid the fall foliage. That night Crook organized his men in heavy woods on the north bank of Cedar Creek. Paramount in Crook's mind was keeping his corps out of sight of the Confederate signal station on Massanutten.

Throughout the day on the 21st, Crook's men stayed concealed in the woods north of Cedar Creek while the VI and XIX corps marched from the area around Strasburg south to Fisher's Hill. Troops of the VI Corps occupied a small hill in front of Fisher's Hill that was a good platform for artillery. Meanwhile, Crook's men waited for the cover of darkness. Then, as the sun began to set, they marched southwest and occupied a position in an area of dense woods slightly north of Hupp's Hill. Crook wore a private's blouse, just in case prying eyes from Massanutten happened to land on him, and he ordered his color bearers to trail their flags, fearing that the bright colors of the Stars and Stripes or flagpole finials would attract attention.

Crook's regiments filed into their positions near Hupp's Hill during the evening of the 21st and rested for several hours. Beginning the next morning, they marched to the eastern face of Little North Mountain, from which they would launch their assault.

By 2 p.m., Crook's two divisions had reached the Back Road, situated at the base of the mountain. Along the road, near St. Stephens Church, Crook's men made their final preparations for the ascent up Little North Mountain and the subsequent attack. Knapsacks were piled, and the men, remembered one soldier from the 116th Ohio, 'arranged canteens and bayonet scabbards so that no noise would be made by them.' Crook's men had managed to maintain secrecy throughout the march, but that effort would be wasted if the Yankees revealed themselves as they climbed up the slopes of the mountain.

To distract Early's men from the events on their left flank, Sheridan directed Emory and Wright to increase their activity along the Rebel front. While the large majority of Early's men were preoccupied with Emory and Wright, the VIII Corps moved into position along the eastern face of Little North Mountain. The march was a difficult one, and all organization in Hayes and Thoburn's columns was lost as they moved along the rocky precipice.

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