 McClellan's plan was to connect the Manassas Gap Railroad and the W&P Railroad with a line between Winchester and Strasburg, creating a "complete circle of rails" from the Union capital at Washington, D.C., to the Shenandoah Valley by either the B&O or O&A.On May 23, 1862, Colonel Turner Ashby and the 7th Virginia Cavalry, during the Valley Campaign of 1862, tore up rails in the direction of Strasburg, while Colonel Thomas T. Munford's 2nd Virginia Cavalry "wrecked track and bridges as far east as Thoroughfare Gap".The Battle of Tom's Brook on October 9, 1864 was fought in significant part directly upon the line of the Manassas Gap Railroad.