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On June 23rd, 14,000 Confederates, half of them barefoot, filed into columns and began marching down the Shenandoah Valley. With Maj. Gen. David Hunter's Union army withdrawing beyond the Alleghenies, leaving Washington,D.C. exposed, Lt. Gen. Jubal A. Early's veterans marched swiftly north, hoping to force Lt. Gen. Ulysses S. Grant to detach part of his army to defend the capital. On July 2nd, the Confederates entered Winchester, where Early divided his army, sending one force against Harpers Ferry while the 2nd command continued toward Martinsburg, West Virginia. Four days later, the Confederate Army of the Valley encamped beyond the Potomac River.
Receiving new orders from Gen. Robert E. Lee, Early detached a cavalry brigade toward Baltimore to cut communications and assist in a scheme to free 18,000 Confederate prisoners at Point Lookout, Maryland. Shoes arrived, and on the 8th, Early crossed South Mountain. He exacted a ransom of $20,000 from Haggerstown, then entered Frederick, whose citizens added $200,000 to Confederate coffers on the 9th.
East of Frederick behind the Monocacy River, Union soldiers under Maj. Gen. Lew Wallace were deployed, stubbornly resisting 5 Confederate assaults before withdrawing late in the day. Wallace's fierce defense delayed Early's advance for a crucial day. The Confederates, suffering from stifling heat and choking dust, reached the defenses of Washinton on the afternoon of the 11th. Early was too late. Veterans hurried northward by Grant from Petersburg manned the the fortifications. The Confederates probed the defenses the next day before retreating that night.
The audacious raiders, burdened with booty and supplies, eluded and then repulsed an inept Union pursuit. Though the scheme to free the prisoners failed, Early had fulfilled Lee's orders by relieving the pressure on the Confederate troops defending Petersburg. As the crusty Confederate told an officer,"Major, we haven't taken washington, but we've scared Abe Lincoln like hell!"