On the evening of July 4, 1863, the Battle of Monterey Pass became one of the most confusing engagements of the American Civil War as Union cavalry under General Judson Kilpatrick met the Confederate 1st Maryland Cavalry, Company B, under Captain George Emack at the approach to Monterey Pass, where Emack’s small guard was reinforced by one cannon from Captain William Tanner’s battery. In darkness and a blinding thunderstorm, Confederate artillerists opened fire, and after the confusion briefly cleared, the Confederates charged and pushed Kilpatrick back before falling back to Red Run, where fighting continued for several hours amid lightning flashes and muzzle fire. The battle spread across Fairfield Gap and into Leitersburg, Maryland, and by 3:30 a.m. on July 5, Union cavalry had reached the turnpike and a Confederate wagon train, capturing and destroying seven miles of wagons and taking 1,000 prisoners on the way toward Ringgold, Maryland. At Leitersburg, another two miles of wagons were destroyed and several hundred more prisoners were taken. The Union cavalry lost 75 men in the battle. By dawn the fighting had ended, and the Confederate army continued using Monterey Pass in its retreat from Gettysburg, while the Union cavalry moved to Smithsburg, Maryland, where it was attacked by Confederate General J.E.B. Stuart, then fell back to Boonsboro, Maryland, arriving shortly after midnight on July 6, 1863.

Photo: Devry Becker Jones

Blue Ridge Summit, Pennsylvania · USA