— Early's 1864 Attack on Washington —
In June 1864, Confederate Gen. Robert E. Lee sent Gen. Jubal A. Early corps from Richmond battlefields to the Shenandoah Valley to counter Union Gen. David Hunter army. After driving Hunter into West Virginia, Early invaded Maryland to attack Washington, D.C., draw Union troops from Richmond, and release Confederate prisoners held at Point Lookout. On July 9, Early ordered Gen. Bradley T. Johnson cavalry brigade eastward to free prisoners. The next day, Johnson sent Maj. Harry Gilmor regiment to raid the Baltimore area. Union Gen. Lew Wallace delayed Early at the battle of Monocacy on July 9. Federal reinforcements soon strengthened the capital defenses. Early attacked there near Fort Stevens on July 11-12 and then withdrew to the Shenandoah Valley with the Federals in pursuit. He stopped at Cool Spring on July 17-18. Despite failing to take Washington or free prisoners, Early succeeded in diverting Federal resources.
Confederate Gen. Jubal A. Early's Army of the Valley entered Middletown from the west on the National Road on July 7, 1864. Confederate Maj. Harry Gilmor, 2nd Maryland Cavalry Battalion, demanded that each family in town provide a loaf of bread and a piece of meat to his soldiers.
The next day, Confederate Gen. Robert Ransom, Jr., demanded that 8,000 rations be provided in two hours. This second requirement was met but depleted the town of most of its meat, sugar, and coffee.
The Confederates made a third and final "forced request" later that evening, when Early demanded a $5,000 ransom from the town's residents. Burgess William J. Ervin pleaded that the sum was too high for his small town to pay. Early modified the terms to require the payment of $1,500 by 7 A. M. on July 9, and for the remaining $3,500 to be paid with the help of residents from the surrounding area by 6 P.M. The town paid the first part of the ransom while most of Early's army began marching eastward across Catoctin Mountain into Frederick. Early left an infantry brigade in Middletown to collect the second part. As the deadline approached, however, Union Cavalry action in the brigade's rear (to the west) prompted the brigade to leave Middletown. The Confederates never did collect the last $3,500.