The Fight at Monterey Pass (or Gap)[3] was an American Civil War military engagement beginning the evening of July 4, 1863, during the Retreat from Gettysburg.

A Confederate wagon train of Lt. Gen. Richard S. Ewell's Second Corps, Army of Northern Virginia, withdrew after the Battle of Gettysburg, and Union cavalry under Brig.

His ability to supply his army by living off the Pennsylvania countryside was now significantly reduced and the Union could easily bring up additional reinforcements as time passed, whereas he could not.

Prior to the movement of the infantry and artillery, however, Lee was concerned with removing his long train of wagons, supplies, and wounded men over South Mountain and into the Cumberland Valley.

[4] While Imboden's wagons moved northwest, Lee designated a shorter route for his three corps: southwest through Fairfield and over Monterey Pass to Hagerstown.

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.

[5] However, the first traffic on the Fairfield Road had begun on the evening of July 3, when Ewell, concerned about the logistical challenges of the impending retreat, sent his corps trains and herds of captured cattle ahead of his main body.

The wagons headed for Monterey Pass followed the route of Maj. Gen. George Pickett's division, which was moving to the rear as escorts for the Union prisoners of war from the battle.

Gen. Judson Kilpatrick's cavalry division joined up with the brigade of Col. Pennock Huey at Emmitsburg, Maryland, and they were ordered to locate and destroy "a heavy train of wagons" that had been spotted by a Union signal station.

Recognizing the vulnerability of Ewell's immense wagon train in the narrow Monterey Pass, Jones asked permission from Stuart to use his entire brigade to defend it.

Gen. George A. Custer, a brigade commander under Kilpatrick, received intelligence from a local civilian that the rear of Ewell's wagon train was approaching a large summer resort hotel named Monterey Springs, which sat atop the Pass.

The tiny group of Marylanders, supported by a few cavalrymen from the 4th North Carolina of Robertson's Brigade, had delayed the Union advance for nearly five hours.

[12] At about 3 a.m. on July 5, as the Michigan Brigade continued to move slowly forward, Kilpatrick sent in the 1st West Virginia Cavalry under Major Charles E. Capehart.

[14] Union troopers rode all the way through the wagon train until they reached Ewell's infantry and captured large numbers of prisoners before returning to repeat the effort.

Erecting substantial defensive works, they awaited the arrival of the Union army, which had been pursuing over longer roads more to the south of Lee's route.

Before Meade could perform adequate reconnaissance and attack the Confederate fortifications, Lee's army escaped across fords and a hastily rebuilt bridge.