Pleasonton Looks for Lee – Finds Stuart Instead

June 17, 1863 (Wednesday)

Pleasonton: Look, I'm doing my best!
Pleasonton: Look, I’m doing my best!

General Joe Hooker, commanding the Union Army of the Potomac, knew that at least some of the Confederate Cavalry under Robert E. Lee had crossed into Pennsylvania. Reports from Harrisburg as well as Darius Couch, former II Corps commander who was now in charge of the Department of the Susquehanna, informed him that the Rebels were circulating in the Chambersburg area. This was all well and good, but Couch’s men, thought Hooker, should be able to handle it. His own focus had to be upon the main body of Lee’s Army, but he had no real idea where it was. He knew that Richard Ewell’s Corps was near or on the Potomac River, but the location the corps of James Longstreet and A.P. Hill were but a mystery.

Hooker should have been able to rely upon his cavalry to gather the details, but the troopers under General Alfred Pleasonton had not yet ventured close to the Confederate lines. He knew that Lee’s army was marching along the Blue Ridge Mountains, but the problem was that the passes were heavily guarded by Jeb Stuart’s Cavalry, finally regrouped after their surprise at Brandy Station. Nobody was even a little impressed with Pleasonton’s ability to gather information and they were not shy about letting him know it.

So on the morning of this date, Hooker ordered Pleasonton to “put the main body of your command in the vicinity of Aldie, and push out reconnaissance towards Winchester, Berryville, and Harpers Ferry.” He was to “obtain information of where the enemy is, his force, and his movements.”

Pleasonton first sent a single regiment on a 100-mile route through Louden County – stomping grounds of the feared John Singleton Mosby. It was also where Pleasonton predicted that Stuart’s main body would be. He wanted this regiment, under the command of Alfred Duffie, to focus upon Thoroughfair, Ashby’s and Snicker’s Gaps in the Bull Run Mountains. He was to end up in Middleburg and get in contact with Pleasonton, who would be in Aldie, ten miles to the west. With only 300 men, things looked more than a bit risky for Col. Duffie.

When the regiment crossed Thoroughfare Gap, it was confronted by an entire brigade of Rebel cavalry approaching the gap. The Confederates halted to take in the situation. Duffie, though greatly outnumbered, did not. But neither did he attack. He threw out a heavy skirmish line and skirted behind them, making Hopeville on the road to Middleburg.

Along the way, Duffie captured a Confederate scout who told him that the brigade behind him had been under James Chambliss. He also mentioned that the Federals had just missed Jeb Stuart himself, riding with Fitz Lee’s Brigade. They were on their way north to Aldie.

Here's a big ol' map.
Here’s a big ol’ map.

While Duffie was marching through Thoroughfair, Pleasonton left with the rest of his Cavalry Corps, moving from Manassas Junction toward Aldie, a small town on the northern end of the Bull Run Mountains. Nine miles before it, Pleasonton ordered his division commander, David Gregg, to send a brigade forward. Gregg selected Judson Kilpatrick, a daring, but erratic commander who was looking for a fight.

He found one as they approached the town, chasing Rebel pickets back into the streets. As more Confederates joined the party, they charged into Kilpatrick’s boys, tossing them back. Kilpatrick now had time to assess the situation. The Rebels were just coming up and he figured that if they could clear out Aldie, they would find the troops that the enemy cavalry was screening. They attacked, but it was a piecemeal affair. Gregg would only send in one brigade.

The Rebels turned out to be from Fitz Lee’s Brigade of Stuart’s Cavalry. When the Federals first attacked, they were just arriving in Aldie, where they planned to camp for the night. The fight was vicious and bold, lasting four hours, most of which was constant fighting.

The fight was not quite a draw, but not far from it. Kilpatrick had bested the Rebels, but could not drive them from the gaps screening the Confederate army. Towards the end of the fighting, the Confederates received orders from General Stuart to fall back to Middleburg – there were apparently Yankees about. The Rebels disengaged and fell back, leaving the passes guarded. Kilpatrick, Gregg, and Pleasonton did not pursue.

The fighting at Aldie
The fighting at Aldie

The Yankees in question were the single regiment under Alfred Duffie, who was still dealing with the fact that Confederate brigades were blocking his advance and retreat. He could not enter Middleburg, but could not head back through Thoroughfare Gap. He had no way of knowing that the brigade that had been in Middleburg was sent north to fight at Aldie.

But when Duffie’s regiment made their appearance, Jeb Stuart, who had established his headquarters in the town, made a hasty getaway, recalled Lee’s Brigade, and sent word to Chambliss and another brigade under Beverly Robertson to converge upon Middleburg.

When Duffie entered the town, it was mostly abandoned. Still, rumors and scouts noted three Rebel brigades closing in quickly. He dispatched two couriers to Aldie, hoping to find someone there who could help. He found Judson Kilpatrick, fresh from the day’s battle, but he refused to do anything. David Gregg, next up the line, also refused. And though Gregg shared the news with General Pleasonton, he did nothing at all that night, abandoning Col. Duffie in Middleburg, where he was now very much surrounded.

Duffie is alone again.
Duffie is alone again.

The Federals had retreated to a farm outside of town, but that too was surrounded. There was nothing that Duffie could do aside from scatter or surrender. Since the latter was the last thing on his mind, the regiment was thrown to the wind. It was every man for himself, and most of the men were captured. Duffie would return to Centerville the next day with only eighty-four troopers.

All the while, General Lee’s Army of Northern Virginia was marching toward the Potomac. Most of Ewell’s Corps was now on its banks at Williamsport. General A.P. Hill’s Corps had mostly cleared Culpeper, far to the south, while James Longstreet brought up the center.

At the end of the day, General Hooker was no closer to finding Lee’s main body. All he could say for sure was that there was no Rebel infantry on his side of the Blue Ridge Mountains. This was, of course, not true, as Jeb Stuart’s screens at Aldie prevented Pleasonton from finding out that John Bell Hood’s Division of Longstreet’s Corps was at Upperville, ten miles west of Middleburg, where Duffie’s regiment met a horrible end.1

  1. Sources: Here Come the Rebels by Wilbur Nye; Gettysburg by Stephen Sears; The Gettysburg Campaign by Edwin Coddington; Official Records, Series 1, Vol. 27, Part 1, p50. []


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