Having commenced his raid on June 25, Stuart almost immediately ran, literally, into a roadblock. At Haymarket, Va., Stuart discovered that Union Maj. Gen. Winfield Scott Hancock’s II Corps was already occupying the road on which Stuart expected to move. Not wanting to engage an infantry corps, Stuart was content to fire off a few artillery rounds and then let Hancock continue on his way, while Stuart spent most of the day grazing his horses in a field nearby. Stuart later claimed that he had sent a message to Lee reporting Hancock’s movements, a report that undoubtedly would have set off warning bells in Lee’s quicksilver mind, but the message never arrived.

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With this early setback, Stuart made his first–and in many ways his most controversial–decision. Many believed, then and later, that in the face of the enemy movement north, Stuart no longer met Lee’s condition to move without hindrance and should have turned back immediately. Lee’s orders did not define exactly what constituted a hindrance, however, and Stuart obviously did not consider Hancock’s rapidly departing corps as a sufficient hindrance to cause him to turn back. At any rate, the orders left it up to him to choose the most expeditious route to take to rejoin the army.

On the evening of June 25, the distance between Stuart’s camp and Shepherdstown, the nearest ford west of the mountains, was more than 60 miles. Stuart could not possibly have reached Shepherdstown before the evening of June 27 or the passes at South Mountain before late the next day. That would still have left him 60 miles from York, where he expected to meet Maj. Gen. Jubal Early’s division of Ewell’s corps. Assuming that he did not encounter further enemy opposition, Stuart reasoned that he still could not have reached York until late on June 30. He believed he could get there on his current route just as quickly. He also expected that the information he had forwarded regarding Hancock’s movement would cause Robertson and Jones to spring into action and rejoin Lee’s army. Based on these expectations and the chance to obey at least part of Lee’s initial order to wreak havoc on the Union rear, Stuart determined to continue his raid by making a slight detour around the enemy’s line of march.

While Stuart was continuing his ride–crossing the Potomac at Rowser’s Ford, tearing up a portion of the C&O Canal and snapping up whatever unwary Federals crossed his path–Lee was inching forward into Pennsylvania. As late as June 27, Lee was telling Brig. Gen. Isaac Trimble, I have not yet heard that the enemy have crossed the Potomac, and am waiting to hear from General Stuart. He was still waiting to hear from Stuart when the cavalry leader reached Rockville, Md., around noon on June 28. While lingering in the area to destroy telegraph lines, Stuart learned that a large, heavily laden wagon train was nearby, heading for the Union army. Here, Stuart made his second controversial decision of the raid. Succumbing to temptation, but also believing that he was following Lee’s orders to hurt the enemy whenever possible, Stuart attacked and captured the 8-mile-long train. However, it took him several hours to burn the wrecked wagons, parole prisoners and gather together the widely scattered brigades of Fitz Lee and Chambliss.

A second message to Lee reporting Stuart’s progress was somehow lost, and Stuart fought his way out of Hanover. Unaware of Lee’s location, Stuart proceeded to York, then on to Carlisle, where he was informed that Lee and his men had been in Gettysburg waiting for him. He finally linked up with Lee’s army late in the afternoon of July 2, several days behind schedule and far too late to help with the arrangements of the ongoing battle.

Ever since Stuart reported to Lee in person on the afternoon of the 2nd, the success or failure of his raid has been the subject of intense debate. Certainly, Lee himself was dissatisfied with Stuart’s performance. The exact wording of his opening statement to Stuart has been disputed. According to some, he said simply, Well, General Stuart, here you are at last. Others maintained that Lee asked icily: General Stuart, where have you been? I have not heard a word from you for days, and you the eyes and ears of my army. Whatever Lee said, it was obvious that he was unhappy with his cavalry commander, an unhappiness that was echoed by Lee’s staff officers, particularly Colonel Charles G. Marshall, who later urged Lee to court-martial Stuart for disobeying orders. The next day, while Stuart ineffectually attacked the Union rear, the Battle of Gettysburg was lost.

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