21 June 2009 by Published in: Union Cavalry 4 comments

146 years ago today, the Union cavalry, supported by Col. Strong Vincent’s infantry brigade of the Army of the Potomac’s Fifth Corps, defeated Jeb Stuart’s cavalry at the Battle of Upperville. Upperville is significant for a variety of reasons, but mainly because it represents the first time that the Union cavalry defeated Stuart’s men on the field of battle and held the battlefield at the end of the day. As they had at Brandy Station 12 days earlier, John Buford’s Federal division and William E. “Grumble” Jones’ Confederate brigade bore the brunt of the day’s fighting. Late in the day, a combined assault by Buford and David Gregg, supported by Vincent’s infantry, shattered Stuart’s lines at Upperville and sent his troopers flying from the field for the first time.

They fell back to the mouth of Chester Gap, the gateway to the Shenandoah Valley, and the support of Lt. Gen. James Longstreet’s First Corps infantry beyond. Fortunately for Stuart and the Confederates, the Federals did not press their advantage and did not discover the presence of the main body of Longstreet’s corps beyond (although Alfred Pleasonton later lied and claimed that he had). The Confederate infantry would have driven the Yankee horsemen off, of course, but they would have gained useful intelligence about the whereabouts of the main body of Lee’s army.

In addition, Stuart lost his favorite aide, the giant Prussian mercenary Maj. Augustus Heros von Borcke, badly wounded in the neck during the final assault by Gregg’s troopers. von Borcke’s wound was thought mortal–although he recovered from it–and it ended his active participation in the American Civil War. It was a serious loss for Stuart, who was very fond of the outgoing, fun-loving German. Stuart himself barely escaped; he reported to his wife Flora that some of Buford’s Regulars of the 1st U.S. Cavalry had been gunning for him but had missed.

However, as he had since Brandy Station, and particularly at Aldie and Middleburg on June 17 and 19, respectively, Stuart managed to keep the active and diligent Union cavalry from locating the body of the Army of Northern Virginia as it advanced down the Shenandoah Valley toward the Potomac River and Maryland. Thus, even though Upperville was a tactical defeat for Stuart’s horsemen–their first at the hands of the Federal cavalry–it remained a strategic victory.

The next day, June 22, Stuart received the orders that led to his eight-day raid during the Gettysburg Campaign, triggering a controversy which still rages to this day. Thus, the Battle of Upperville is worthy of commemoration for a variety of reasons. Here’s to the cavalrymen of both sides who fought there 146 years ago today.

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  1. Jeff Mancini
    Sun 21st Jun 2009 at 4:41 pm

    Eric: Isn’t it safe to conclude that the Federal effort at Upperville was a dramatic improvement of the previous two battles. Duffie ‘s 1st Rhode Island was severly bludgeoned four days earlier at Middleburg and just two days later Kilpatrick led the 1st Massachusettes into a trap at Aldie and that unit was grinded up terribly. So Upperville was a needed rally. I conclude that the Federal Cavalry with its growing strength in both numbers and equipment was not going to let up on Stuart’s troopers and Upperville started that winning trend so slightly tasted at Brandy Station. The march northward meant an extended line and that put extra pressure on Rebel pickets as they had to relentlesly screen the ANV and still hope to accomplish some foraging of their own.

  2. Jeff Mancini
    Sun 21st Jun 2009 at 10:42 pm

    Eric: Actually I think I have have the sequence of those two units demises swapped and thus the 1st Mass. got slammed four days earlier at Aldie and then Duffie’s demise with the 1st Rhode Island at Middleburg occurred on the 19th. Both situations,however,illustrated that despite its new found boldness that the Union Cavalry was still going to get its nose bloodied on numerous occasions and the perceived demise of the Rebel’s on horseback beginning with the Kelly’s Ford Raid months earlier was being exagerated as well.

  3. Mon 22nd Jun 2009 at 9:02 am

    I intended to post a “trip report” (and I use the term loosely here as it would actually be the sum of two dozen “trips” now) of the Loudoun Valley fights.

    Goose Creek Bridge in particular interests me as a small example of the three combat arms working within the same battlespace. Beautiful bridge, and a lot of interesting characters to discuss.

    But I’ve gotten distracted lately with the darned pontoon bridges down the road from my house at Edwards Ferry.

  4. Stevan Meserve
    Wed 01st Jul 2009 at 12:09 pm

    If I may play nitpicker, Vincent’s infantry was not involved in the fighting at Upperville, neither along the turnpike nor on Trappe Road. The infantry, having marched 14 miles and skirmished with Stuart’s cavalry several times before reaching Goose Creek, dropped out after helping to capture the bridge there.

    “Grumble” Jones (accompanied by Fitz Lee’s brigade under the command of Col. Chambliss) was not assaulted by Buford and David Gregg, but by Buford alone. Gregg was, at that same time, heavily engaged with Wade Hampton’s brigade and Beverly Robertson’s Carolinians in the town of Upperville. Nearly two miles separated the two battles.

    The only “flying” from the field was done by the Carolinians when they were first attacked in the Ivy Hill Cemetery east of town. Hampton’s men not only blunted Gregg’s assault, but actually held Judson Kilpatrick prisoner briefly before withdrawing at a walk around, rather than through, the town. Even the Carolinians rallied west of town and stopped the Union advance well east of the Blue Ridge. The gap Pleasonton so desperately wanted to reach, by the way, was Ashby’s Gap. Chester Gap is near Front Royal.

    Heros von Borcke was wounded in the fighting in Middleburg the day before the Battle of Upperville.

    Technically, you could call all three of the Loudoun Valley battles tactical defeats for Stuart (which the Richmond newspapers did with a vengeance) since the Union cavalry was left in control of the entire valley when Pleasonton decided, for some unknown reason, to withdraw all the way to Aldie on June 22 instead of pressing ahead to the Blue Ridge gaps. Neither Stuart nor his men liked that kind of fighting, but their mission, at which they succeeded admirably, was to trade ground for time. John Buford would perform the same mission when facing Heth’s troops at Gettysburg.

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