The week leading up to Gettysburg was an arduous one for Maj. Gen. James Ewell Brown (Jeb) Stuart and his cavalry division. Stuart’s task was gathering intelligence while screening the right flank of Richard Ewell’s Second Corps as it moved north. Leaving two brigades behind under Brig. Gens. Beverley Robertson and William Jones to operate with Lee, Stuart mounted his remaining three brigades (about 5,600 men) early on June 24. The movement, based upon discretionary orders, would eventually become a long-distance ride around the entire Army of the Potomac.
Once the Union army moved north after General Lee’s infantry, Stuart found it difficult to get around and ahead of its component pieces. Within a short time, he was effectively cut off from the Army of Northern Virginia. On June 28 near Rockville, Maryland, he captured 125 wagons loaded with supplies. The supplies were useful, but the wagons slowed him down. Unable to locate Lee, Stuart rode to York, Pennsylvania and then to Carlisle seeking information. Early on July 2, Stuart learned Lee was fighting a battle at Gettysburg. Between June 24 and July 2, his exhausted troopers and jaded horses rode 200 miles and fought a series of skirmishes (Thoroughfare Gap, Fairfax Court House, Rockville, and Carlisle), and three sharp actions: Westminster, Hanover, and Hunterstown.1
After riding all night from Carlisle, Stuart arrived at Gettysburg late on the afternoon of July 2 while preparations were underway to launch the en echelon attack against the Army of the Potomac. After a cold meeting between General Lee and his subordinate, a plan was crafted for Stuart to operate beyond the army’s left flank, and to watch for any opportunity to assault the rear areas of the enemy. Back in their saddles early on July 3, Stuart’s cavalry rode out on the York Pike. A portion of Albert Jenkins’ cavalry brigade (which was under Lt. Col. Vincent Witcher, 34th Virginia Battalion), led the column. Behind Witcher rode Col. John Chambliss’ Brigade, followed by Capt. William Griffin’s and Capt. Thomas Jackson’s batteries. Next was Brig. Gen. Wade Hampton’s Brigade, followed by a section of Capt. Charles Green’s battery (which was not horse artillery). Brigadier General Fitz Lee’s Brigade brought up the rear.2
Confronting Stuart’s 6,000-6,500 men and thirteen guns were brigades under Cols. John McIntosh and Irvin Gregg, both of Brig. Gen. David Gregg’s Second Cavalry Division. Gregg’s brigade tangled with Ewell’s Second Corps on July 2 at Brinkerhoff Ridge, and was now east of the ridge guarding the Army of the Potomac’s right rear sector. McIntosh’s brigade reached the field at 1:00 p.m. on July 3. General Gregg’s orders were to move his division south to guard the right flank of the XII Corps, but he hesitated when he realized the strategic importance of this area. A brigade under Brig. Gen. George Custer and Lt. Alexander Pennington’s battery (Brig. Gen. Kilpatrick’s division), at Gregg’s request, moved to occupy the pivotal position at the intersection of Hanover and Low Dutch roads. Dismounting two companies each from the 5th and 6th Michigan, Custer threw them forward down both roads.3
Stuart intended to leave York Pike and ride south to Hanover Road before riding toward Baltimore Pike. This move would place him close to Ewell’s Corps and the Federal rear. When he reached Cress Ridge (between York Pike and Hanover Road) about noon, Stuart dismounted the 34th Virginia Battalion. The 170 men took possession of the Rummel barn, and shook out along a fence line left of the building. The remainder of the brigade deployed on both sides of the 34th Virginia Battalion. Chambliss’ troopers took up a position behind Witcher. The former’s right regiment, the 13th Virginia, extended to the George Trostle farm. Stuart deployed artillery and fired several shots in an unsuccessful effort to flush out the enemy.4
When Custer heard the firing he reoriented his brigade and the battery in its direction and sent the dismounted 5th Michigan across Hanover Road. Cavalry commander Maj. Gen. Alfred Pleasonton agreed to allow Gregg to return to his former position if Custer was released to return to Kilpatrick. Gregg agreed and his two brigades rode to the contested area.5