Retreat From Gettysburg - Fairfield and Monterey Pass

Fairfield and Monterey Pass

Further information: Battle of Fairfield, Battle of Monterey Pass

After dark on July 4, Hill's Third Corps headed out onto the Fairfield Road, followed by Lt. Gen. James Longstreet's First Corps and Richard S. Ewell's Second Corps. Lee accompanied Hill at the head of the column. He ordered Stuart to post Col. John R. Chambliss's and Brig. Gen. Albert G. Jenkins's brigades (the latter commanded by Col. Milton Ferguson) to cover his left rear from Emmitsburg. Departing in the dark, Lee had the advantage of getting several hours head start and the route from the west side of the battlefield to Williamsport was about half as long as the ones available to the Army of the Potomac.

Meade was reluctant to begin an immediate pursuit because he was unsure whether Lee intended to attack again and his orders continued that he was required to protect the cities of Baltimore and Washington, D.C. Since Meade believed that the Confederates had well fortified the South Mountain passes, he decided he would pursue Lee on the east side of the mountains, conduct forced marches to quickly seize the passes west of Frederick, Maryland, and threaten Lee's left flank as he retreated up the Cumberland Valley. However, Meade's assumption was wrong—Fairfield was lightly held by only two small cavalry brigades and the passes over South Mountain were not fortified. If Meade had secured Fairfield, Lee's army would have been forced to either fight its way through Fairfield while its rear was exposed to the Army of the Potomac at Gettysburg or to take his entire army through the Cashtown Pass, a much more difficult route to Hagerstown.

On July 3, while Pickett's Charge was underway, the Union cavalry had had a unique opportunity to impede Lee's eventual retreat. Brig. Gen. Wesley Merritt's brigade departed from Emmitsburg with orders from cavalry commander Maj. Gen. Alfred Pleasonton to strike the Confederate left and rear along Seminary Ridge. Reacting to a report from a local civilian that there was a Confederate forage train near Fairfield, Merritt dispatched about 400 men in four squadrons from the 6th U.S. Cavalry under Major Samuel H. Starr to seize the wagons. Before they were able to reach the wagons, the 7th Virginia Cavalry, leading a column under Confederate Brig. Gen. William E. "Grumble" Jones, intercepted the regulars, starting the minor Battle of Fairfield. Taking cover behind a post-and rail fence, the U.S. cavalrymen opened fire and caused the Virginians to retreat. Jones sent in the 6th Virginia Cavalry, which successfully charged and swarmed over the Union troopers, wounding and capturing Starr. There were 242 Union casualties, primarily prisoners, and 44 casualties among the Confederates. Despite the relatively small scale of this action, its result was that the strategically important Fairfield Road to the South Mountain passes remained open.

Early on July 4 Meade sent his cavalry to strike the enemy's rear and lines of communication so as to "harass and annoy him as much as possible in his retreat." Eight of nine cavalry brigades (except Col. John B. McIntosh's of Brig. Gen. David McM. Gregg's division) took to the field. Col. J. Irvin Gregg's brigade (of his cousin David Gregg's division) moved toward Cashtown via Hunterstown and the Mummasburg Road, but all of the others moved south of Gettysburg. Brig. Gen. John Buford's division went directly from Westminster to Frederick, where they were joined by Merritt's division on the night of July 5.

Late on July 4, Meade held a council of war in which his corps commanders agreed that the army should remain at Gettysburg until Lee acted, and that the cavalry should pursue Lee in any retreat. Meade decided to have Brig. Gen. Gouverneur K. Warren take a division from Maj. Gen. John Sedgwick's VI Corps—the most lightly engaged of all the Union corps at Gettysburg—to probe the Confederate line and determine Lee's intentions. Meade ordered Butterfield to prepare for a general movement of the army, which he organized into three wings, commanded by Sedgwick (I, III, and VI Corps), Maj. Gen. Henry W. Slocum (II and XII), and Maj. Gen. Oliver O. Howard (V and XI). By the morning of July 5, Meade learned of Lee's departure, but he hesitated to order a general pursuit until he had received the results of Warren's reconnaissance.

The Battle of Monterey Pass began as Brig. Gen. Judson Kilpatrick's cavalry division arrived near Fairfield on July 4 just before dark. They easily brushed aside Brig. Gen. Beverly Robertson's pickets and encountered a detachment of 20 men from the Confederate 1st Maryland Cavalry Battalion, under Capt. G. M. Emack, that was guarding the road to Monterey Pass. Aided by a detachment of the 4th North Carolina Cavalry and a single cannon, the Marylanders delayed the advance of 4,500 Union cavalrymen until well after midnight. Kilpatrick was not able to see anything in the dark and considered his command to be in "a perilous situation." He ordered Brig. Gen. George A. Custer to charge the Confederates with the 6th Michigan Cavalry, which broke the deadlock and allowed Kilpatrick's men to reach and attack the wagon train. They captured or destroyed numerous wagons and captured 1,360 prisoners—primarily wounded men in ambulances—and a large number of horses and mules.

Following the fight at Monterey, Kilpatrick's division reached Smithsburg around 2 p.m. on July 5. Stuart arrived from over South Mountain with the brigades of Chambliss and Ferguson. A horse artillery duel ensued, causing some damage to the small town. Kilpatrick withdrew at dark "to save my prisoners, animals, and wagons" and arrived at Boonsboro (spelled Boonsborough at that time) before midnight.