General Robert E. Lee, commanding the Confederate Army of Northern Virginia, instructed his cavalry commander, Major General J.E.B. “Jeb” Stuart, to take 1,800 horsemen and ride around Major General George B. McClellan’s relatively stagnant Army of the Potomac. Stuart was “to gain all information of the position, force, and probable intention of the enemy which you can,” much like Stuart’s ride around the Federals four months prior. He was to observe strict secrecy and “arrest all citizens that may give information to the enemy.”
Stuart also had orders to seize any prominent Pennsylvanians so “that they may be used as hostages, or the means of exchanges for our own citizens that have been carried off by the enemy.” Stuart was to treat these people “with all the respect and consideration that circumstances will admit.”
Finally, Lee directed Stuart to wreck the Cumberland Valley Railroad bridge over the Conococheague River near Chambersburg, Pennsylvania. This connected to the Pennsylvania Railroad and the coal fields and iron factories of Pittsburgh, thus serving as a vital artery to the Federal supply line.
Stuart assembled his troopers at Darkesville, south of Martinsburg in western Virginia, on October 9. They rode toward Williamsport that afternoon and early evening, stopping to camp for the night at Hedgesville. The next morning, the Confederates crossed the Potomac at McCoy’s Ford above Martinsburg. They captured several Federal pickets, but some escaped to warn of the Confederates’ approach. When General-in-Chief Henry W. Halleck learned the news, he notified McClellan that “not a man should be permitted to return to Virginia.”
The Confederates moved through Maryland’s narrow panhandle along the National road. They captured a signal station, preventing the Federals from signaling their location. As the Federals began mobilizing to find them, Stuart’s men turned north and entered Pennsylvania. The horsemen had observed strict prohibitions on looting in Maryland, since they still hoped that state might join the Confederacy. Pennsylvania received no such protection. Many farms and homes were plundered.
After a 40-mile ride, the Confederates descended on Chambersburg by nightfall. Stuart demanded the town’s surrender, but all Federal officials had already fled except for newspaper editor Alexander McClure and Judge Francis M. Kimmell. McClure surrendered to Brigadier General Wade Hampton, whom Stuart appointed as the town’s “military governor.”
The Confederates bivouacked that night in the streets of Chambersburg, and Stuart reported that all civic officials had abandoned the town. McClure showed the Confederates such kind hospitality that they disregarded orders to take him hostage.
The mood was tense in Washington as news of Stuart’s raid trickled in. Navy Secretary Gideon Welles wrote in his diary, “We have word which seems reliable that Stuart’s Rebel cavalry have been to Chambers-burg in the rear of McClellan, while he was absent in Philadelphia stopping at the Continental Hotel. I hope neither statement is correct. But am apprehensive that both may be true.” McClellan had left his army to visit his wife and baby, leaving behind no plan in case of attack.
Stuart led his men out of Chambersburg at dawn on the 11th, worried that last night’s hard rain might have flooded the Potomac crossings. Before leaving, the troopers burned the supply depot, railroad machine shops, trains, and any military equipment they could not take. They also cut the telegraph wires and stole local horses. However, they could not burn the iron Conocoheague Bridge, and a bank employee had escaped from Chambersburg with all the money from the town’s bank vault.
The Confederates moved east, expecting McClellan to send Federals to cut off their upper Potomac escape route. They rode beyond the Blue Ridge into Cashtown, Pennsylvania, where they stopped to feed their horses and raid the Cashtown Inn. Stuart then moved south, avoiding Gettysburg and passing through Emmitsburg, Maryland, in late afternoon. The rains actually helped the Confederates because the horses created no dust clouds that could alert nearby Federals of their presence.
At Emmitsburg, Stuart prohibited any residents from leaving town, fearful that someone might run off to give the Federals his location. Most civilians expressed support for the Confederacy. As the troopers rode out of Emmitsburg, a captured Federal informed Stuart that the Federals awaited him at Frederick, 20 miles away. The troopers bypassed that town and forded the Monocacy River that night.
Federal cavalry began an effort to stop Stuart based on information that McClure provided McClellan. However, McClellan claimed he could spare just 800 horsemen to contend with the Confederates. He dispatched a few cavalry units to pursue the enemy and guard the river fords; he also directed two infantry brigades to protect the bridge spanning the Monocacy River. Another division was sent to guard Poolesville.
On the 12th, Stuart and his men passed through Hayattstown and slipped between two Federal cavalry units near Poolesville. After executing several deceptive maneuvers to throw the Federals off their track, the Confederates crossed the Potomac at White’s Ferry, which was guarded by a single Federal regiment that fell back upon seeing such a large force approaching.
The Federals hurried up to the riverbank just after the Confederates crossed. According to William W. Blackford, who rode with Stuart, “We were not half across when the bank we had left was swarming with the enemy who opened a galling fire upon us, the bullets splashing the water around us like a shower of rain. But the guns from the Virginia side immediately opened on them and mitigated their fire considerably, and we soon crossed and stood once more on Virginia soil.”
The Confederate troopers returned to their base south of Martinsburg the next day. Stuart had failed in his mission to destroy the Conococheague River bridge, but every other aspect of this operation was a resounding Confederate success. Circumventing McClellan’s army for the second time in four months, Stuart’s cavalry covered 126 miles in three days. They had caused an estimated $250,000 in property damage while seizing 1,200 horses, 30 civilian officials who could be exchanged for Confederate prisoners, and valuable intelligence on McClellan’s troop positions. Stuart lost just a few men wounded and two men missing.
The raid embarrassed and infuriated President Abraham Lincoln, especially considering it occurred just before the Federal midterm elections. Lincoln’s secretary, John Nicolay, stated that the president “well-nigh lost his temper over it.” Welles noted in his diary:
“We have the mortifying intelligence that the Rebel cavalry rode entirely around our great and victorious Army of the Potomac, crossing the river above it, pushing on in the rear beyond the Pennsylvania line into the Cumberland Valley, then east and south, recrossing the Potomac below McClellan and our troops, near the mouth of the Monocacy… It is humiliating, disgraceful… It is not a pleasant fact to know that we are clothing, mounting, and subsisting not only our troops but the Rebels also… His (McClellan’s) opponents will triumph in this additional evidence of alleged inertness and military imbecility.”
General Lee reported to Richmond on the 14th, “The cavalry expedition to Pennsylvania has returned safe… It had crossed the Potomac at Williamsport and re-crossed at White’s Ford, making the entire circuit, cutting communications, destroying arms, and obtaining many recruits.”
The southern press celebrated Stuart’s feat as another sensational and daring ride around the mighty Federals, and even the influential New York Tribune conceded, “The cavalry raid around our entire army… is the one theme of conversation. It was audacious and brilliant.”
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