Monterey Pass is located near Blue Ridge Summit and the historical Mason–Dixon line.

Captain Robert B. Moorman, commanding Company D of the 14th Virginia Cavalry[4] was dispatched eastward from the area between Greencastle, Pennsylvania, and Hagerstown, Maryland, to obtain horses reportedly available from local Southern sympathizers.

[5] After the company passed through Leitersburg, Maryland,[6] and on to Caledonia Furnace; at Monterey the company encountered Bell's Adams County Cavalry[1] and the First Troop, Philadelphia City Cavalry,[citation needed] both temporarily based in Gettysburg.

After a very brief skirmish, the Confederate troops withdrew toward Hagerstown, joining General Richard S. Ewell, who was advancing with a larger force.

[7] Previous combat in the area included a June 21 engagement at Fairfield, and subsequent engagements prior to the Battle of Gettysburg included the first combat of Adams County, Pennsylvania, during the Civil War.