The departure of the Federals was not such a grand event for Jubal Early and his winter-shriveled command in Staunton. Spies in Winchester and soldiers manning the army’s observation and signal station on Massanutten Mountain had already detected signs of the impending Union movement. Nine days earlier, Confederate Private Henry Berkeley confided to his diary: ‘We hear that the Yanks are collecting a very large cavalry force at Winchester and are expected to move up the Valley as soon as the weather permits. I don’t see how it is possible for our little force to make any headway against them. We are only 1,500; they are reported to be 15,000. They will run over us by sheer weight of numbers. Who will be left to tell the tale?’

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Berkeley’s estimation of the Federals’ strength was off by one-third, but his apprehension was shared by his army commander. All winter Early had brooded about his three stinging defeats, particularly the lost opportunity at Cedar Creek. Ungenerously, he had blamed that defeat on his own men, complaining to Lee, ‘We had within our grasp a glorious victory, and lost it by the uncontrollable propensity of our men for plunder.’ He failed to mention his own delay at the time of the initial breakthrough, and he flatly declared that the subsequent Confederate retreat had been ‘without sufficient cause,’ a panic created by ‘an insane dread of being flanked and a terror of the enemy’s cavalry.’ That the army had already been outflanked twice before, at Winchester and Fisher’s Hill, and that the Confederate cavalry had been sent reeling at Tom’s Brook were factors Early neglected to mention.

Robert E. Lee, however, could understand clearly enough what had happened, and in the intervening weeks and months he had proceeded to strip Early of much of his command. The skeleton force that still remained in Staunton, Lee advised Early, was simply there ‘to produce the impression that the force was much larger than it really was.’ Gently, Lee advised Early to do the best he could. Faced with a flurry of alarming reports announcing the enemy’s advance up the valley, Early minded Lee’s advice. He directed Rosser to regather his horsemen, who had temporarily disbanded to winter at their homes, and attempt to delay the Union advance at Mount Crawford, where a covered bridge crossed the North River. At the same time, Early telegraphed Maj. Gen. Lunsford Lomax at Millboro, 40 miles west of Staunton, and ordered him to bring his understrength cavalry division back east. Similar orders went to Brig. Gen. John Echols to dispatch his infantry brigade by rail to Lynchburg, which Early assumed was Sheridan’s ultimate target. Finally, Early had all military stores removed from Lynchburg, in case the town fell to the Federals.

The blue column moved up the macadamized Valley Pike on the 27th, stopping to camp for the night at Woodstock. The next morning, with Custer’s 3rd Division in the lead, the march resumed. Despite a steady rain, spirits were high, with Sheridan informing Grant that ‘the cavalry officers say the cavalry was never in such good condition.’ The mood darkened, at least temporarily, when eight troopers drowned while attempting to swim their horses across the rain-swollen North Fork of the Shenandoah River. ‘[M]any others would have been drowned had it not been for the superhuman efforts of a number of officers and men…who rushed into the stream, and at great personal risk brought them to the shore,’ reported the commander of Custer’s 1st Brigade, Colonel Alexander Pennington. The rest of the army waited for the engineers to put out a pre-constructed pontoon bridge.

As early as February 28, Sheridan made it plain to his officers — if not to Grant — that he had no intention of returning to Winchester following the raid. (Whether he intended to head south and join Sherman, as Grant wanted, Sheridan did not say.) At officers’ call that morning, Sheridan gathered his subordinates together and told them ‘that we were on a big march of not less than 350 or 400 miles,’ Sergeant Roger Hannaford of the 2nd Ohio reported — certainly much longer than an advance and return from Winchester to Staunton would require.

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