Based on Lee’s instructions, Stuart began fabricating a plan for another dramatic cavalry raid that would pass around the rear of the Union army. It is possible, as critics later charged, that the recent disappointments at Brandy Station and Upperville (where the Union cavalrymen gave good accounts of themselves) might have made Stuart more eager than usual for an opportunity to reassert the superiority of his own vaunted cavalry and restore his slightly tarnished reputation. More likely, however, he was simply thinking along the same lines as Lee and Longstreet on how best to use his light cavalry in the upcoming campaign.

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With Lee’s and Longstreet’s rather vague advice in hand, Stuart turned to his most trusted scout, John Singleton Mosby, for information on the best route to take into Pennsylvania. Mosby, who would later find fame as the commanding colonel of an effective independent cavalry unit in northern Virginia, Mosby’s Rangers, was still serving on Stuart’s personal staff. He rode into headquarters on June 23 with word that Stuart could pass safely around the rear of Hooker’s widely dispersed army in western Maryland en route to Pennsylvania. Hooker, said Mosby, was lying idle along a 25-mile-long line from Leesburg, Va., to Thoroughfare Gap, just west of Haymarket, and the Federal line was stretched so thin that Stuart could simply ride through it. It was a dangerously overoptimistic assessment of the military situation, based on the assumption that the Federals would simply sit still and wait for events to overtake them. But Stuart trusted Mosby implicitly and was, at any rate, always ready to accept information that conformed to his own expectations.

Stuart liked the plan so well that he committed it to paper and showed it to the commanders of his two brigades, Brig. Gens. Fitzhugh Lee and Wade Hampton. He then detailed his strategy to Lee and Longstreet. Stuart’s plan called for him to pass through Glasscock Gap, then head northeast, crossing the Potomac at Seneca Ford and joining Ewell in Pennsylvania. Stuart fully expected his cavalry to pass to the rear of the Union army, severing communications between Hooker and his own cavalry commander, Brig. Gen. Alfred Pleasonton, destroying transportation for the Union army, and taking pressure off Lee by creating a diversion and slowing down Hooker’s movements. Once in Maryland, Stuart would wreck the C&O Canal and destroy railroad communications with Washington.

Stuart went to army headquarters at Berryville to await Lee’s approval of his plan. He was sleeping out in the open under a poncho when Lee’s response arrived. Stuart’s adjutant, Major Henry McClellan, opened the letter (clearly marked “confidential”) and woke Stuart to show him the message. Lee had written: “If General Hooker’s army remains inactive, you can leave two brigades to watch him, and withdraw with the three others, but should he not appear to be moving northward, I think you had better withdraw this side of the mountain tomorrow night, cross at Shepherdstown next day and move to Fredericktown [Frederick]. You will, however, be able to judge whether you can pass around their army without hindrance, doing them all the damage you can, and cross the river east of the mountains. In either case, after crossing the river, you must move on and feel the right of Ewell’s troops, collecting information, provisions, etc. Give instructions to the commander of the brigades left behind to watch the flank and rear of the army and (in event of the enemy leaving their front) retire from the mountains west of the Shenandoah, leaving sufficient pickets to guard the passes, and bringing everything clean along the valley, closing upon the rear of the army.”

The second letter from Lee was ambiguous and somewhat illogical, especially when considering his first letter. Initially, Lee had told Stuart he was concerned that Hooker might “steal a march on us and get across the Potomac before we are aware.” His first set of instructions ordered Stuart to link up with Ewell’s right and “guard his flank,” while also “collect[ing] all the supplies you can for the use of the army.” That in itself was a rather contradictory order, especially for a cavalryman famous for his independent raiding sorties.

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