The Manassas Gap Railroad was used during the Great Train Raid of 1861, in which Colonel Thomas J. Stonewall Jackson of the Virginia militia raided the Baltimore and Ohio Railroad and removed, captured or burned 67 locomotives and 386 railway cars, and taking 19 of those locomotives and at least 80 railroad cars onto Confederate railroads. After initially trapping this rolling stock on the Virginia-controlled portion of the Baltimore & Ohio, Jackson immediately helped himself to four small locomotives not too heavy for the flimsy flat-bar rails of the Winchester and Potomac Railroad, and had them sent to Winchester where they were disassembled near Fort Collier, mounted onto special dollies and wagons, and hauled by 40-horse teams down the Valley turnpike to the [Manassas Gap] railroad at Strasburg. Eventually almost all of the B&O locomotives and most of the railroad cars were taken to the Manassas Gap Railroad.