On June 22, 1863, a skirmish erupted at Monterey Pass when Company D of the 14th Virginia Cavalry attacked portions of Union cavalry under Captain Robert Bell and Captain Samuel Randall and several members of the Gettysburg Home Guard. Confederate skirmishers searched the woods on foot along the Emmitsburg and Waynesboro Turnpike, forcing the militia to retreat toward Fairfield by way of Maria Furnace Road, where the chase ended at dusk. On June 28, a twenty-five-man detail of Company C of Cole’s Cavalry passed through Monterey Pass toward Fountaindale and, near Jacks Mountain Road, intercepted Confederate soldiers foraging for horses and supplies; after a brief engagement, all of the raiders were captured. On June 29, Union General John Buford’s cavalry division left Middletown, Maryland, for Pennsylvania, observed Confederate troops marching in the distance at Greencastle from Monterey Pass, received a patriotic welcome from local residents, and reached Fountaindale at 10:00 p.m., where Buford ordered his men to bivouac for a few hours before moving toward Fairfield. At 2:00 a.m. on June 30, Buford sent the 6th New York Cavalry down Furnace Road to cover his left flank while the rest of the division moved along Jacks Mountain Road; both columns encountered Confederate pickets and fought briefly before he broke off the action and moved toward Emmitsburg, Maryland. As the columns passed Monterey Springs, an old man stood beside the road with his hat off and tears streaming down his face, and the men cheered him heartily.