150 Years Ago: Fighting at Upperville

The forth major cavalry action of the Gettysburg campaign concluded this evening 150 years ago at Upperville, Virginia.  As with Middleburg, I’m not going to attempt to improve upon the maps and narrative offered from the ABPP study of the Loudoun Valley cavalry actions.  Instead let me offer some of my favorite photos from visits to those fields over the last few years, with a short narrative for those unfamiliar with the battle.

Upperville actually started in Middleburg.  After securing Mount Defiance along the Ashby’s Gap Turnpike on June 19, Brigadier-General Alfred Pleasonton halted to reset his troopers.  Rains through June 20 provided a good excuse against any aggressive movements. Likewise Major-General J.E.B. Stuart used the break to bring up reinforcements.  Major-General Joseph Hooker still wanted Pleasonton to locate the Confederate main body.  Reports from deserters, refugees, and prisoners was not enough, Hooker wanted someone to see and identify the rebel infantry.  So for June 21, Pleasonton planned to push aside Stuart’s cavalry, essentially continuing the action where it stopped on June 19.  While one force under Brigadier-General David M. Gregg would push down the Turnpike, another column under Brigadier-General John Buford would attempt a flanking march on the road network to the north, generally paralleling the turnpike.  An infantry brigade from the Fifth Corps supported Gregg’s column.  This was Colonel Strong Vincent’s brigade consisting of the 16th Michigan, 44th New York, 20th Maine, and 83rd Pennsylvania.

When the fighting began that morning, Confederates on the high ground at Bittersweet Farm prevented Gregg’s troopers from advancing further.  Federal artillery on Mount Defiance dueled with four Confederate guns of Hart’s Battery.  During the exchange a Federal round found one of Hart’s ammunition chests, resulting in a spectacular explosion.

But what turned the position was Vincent’s infantry.  The 83rd Pennsylvania extended the line far enough to the left that Confederate troopers could not bend further.  This started a pattern which repeated throughout the morning.  At Crummey’s Run and Rocky Creek, dismounted Confederates delayed the advance on the turnpike, but at each position were ultimately flanked by Vincent’s infantry.  Appearance of the infantry prompted the 1st South Carolina Cavalry, acting as rear guard, to fall back from Rector’s Cross Roads.

But with that, Stuart deployed on favorable ground overlooking Goose Creek at a stone bridge on the turnpike.  Two Federal cavalry charges failed to clear the bridge.  As the artillery dueled, once again Vincent’s infantry worked into a flanking position. The 83rd Pennsylvania forded the creek upstream of the bridge and again worked on the flanks of the dismounted rebel cavalry.  A third Federal cavalry charge then gained the bridge.  Confederates then began a hurried retreat towards Upperville.  But it was mid-afternoon and Pleasonton’s troopers were still not past Stuart.

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Goose Creek Bridge

While Gregg’s and Vincent’s men shouldered the Confederates slowly down the turnpike, on the Federal right, Buford was likewise delayed by Confederate blocking actions.  Early in the morning rebel skirmishers delayed crossing of Goose Creek at Benton’s Bridge.  Attempts to bypass were thwarted by muddy roads and fields.  After a two hour delay Buford’s troopers forced a crossing at the partially burnt Benton’s Bridge.

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Modern Bridge over Goose Creek near site of Benton’s Bridge

Once across, Buford faced Colonel Lunsford Lomax leading the 11th and 12th Virginia Cavalry (of Colonel John Chambliss’s Brigade).  Lomax setup a series of roadblocks along Millville Road.  Giving ground only when Federal skirmish lines and artillery compelled him, Lomax managed to delay Buford long enough for Briagider-General William E.  “Grumble” Jones to clear his artillery and trains from danger.

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Wellborne / Millville Road

Around the same time in the mid-afternoon that Stuart fell back from Goose Creek Bridge, Chambliss ordered Lomax to fall back towards Upperville.  He’d bought several hours of time and prevented Buford from enveloping Stuart from the north.  Buford now turned his column south off Millville Road onto Greengarden Road.  He wanted to join in with Gregg against Stuart.

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Panther Skin Creek

But Panther Skin Creek was unfordable, so instead Buford moved on Sunken Road parallel to the creek and in the direction of Trappe Road where Chambliss and Jones took up positions.

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Sunken Road

Meanwhile, Stuart fell back to a rise known as Vineyard Hill outside Upperville.  There a square of hedges offered a favorable position on the south side of the Turnpike. He’d used this position during fighting the previous November while also screening the movements of the Army of Northern Virginia.

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Federal View of Vineyard Hill

A charge by Brigadier-General Judson Kilpatrick’s Brigade, supported by the Reserve Brigade (whom Buford had detached to support Gregg’s column earlier in the afternoon) failed miserably.  A second charge by Kilpatrick fared no better.  With the Federals stalled, Stuart’s two brigades defending the turnpike could withdraw without pressure.

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View from Vineyard Hill

To the north, Buford’s column emerged from the bottoms of Panther Skin Creek and was greeted by the cannon of Chew’s battery positioned on the Thomas Farm to the east of Trappe Road.  Buford’s lead brigade, under Colonel William Gamble emerged from a draw to face a Confederate force nearly twice its size.  A see-saw fight broke out over the Thomas and Ayre Farms that drew in both of Buford’s brigades to face those of Chambliss and Jones.  Chew’s guns, while forming the bulwark of the Confederate line, were the targets of several Federal assaults.  Likewise, several Confederate counterattacks parried those assaults.

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Ayre Farm Fields (north end)

Eventually Chew repositioned his guns west of Trappe Road where he continued to harass the Federals.  Brigadier-General Devin’s brigade finally cleared the Confederates off the Thomas Farm.  But the Federals were unable to keep up the pressure.  Chambliss and Jones, with Chew’s battery, withdrew down Trappe Road to Upperville then followed the turnpike up the Blue Ridge into ever lengthening shadows.

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Gibson Farm Fields west of Trappe Road

Before dusk set in, the last action of the battle played out at the western edge of Upperville at the intersection of Trappe Road and the turnpike. North Carolinians from Brigadier-General Beverly Robertson’s brigade held that gate open for retreating comrades.  Pleasonton deployed his last reserve unit, the brigade of Colonel J. Irvin Gregg.  In a close quarter fight devolving into a melee, the Federals wrested control of the intersection.  Although clear of the town, the Federals were spent and could not pursue further in the growing darkness.  Confederates fell back to the gap, dusted but still game.

Thus ended the battle of Upperville and the series of cavalry battles in Loudoun Valley (and my 1000 word summary of the battle).  Unable to cross the Blue Ridge, Pleasonton could not secure the information Hooker desired.  Stuart could say he accomplished the assigned mission, but would receive public criticism for apparently losing three battles.  From an operational perspective, the sunset at Upperville gave away some precious initiative to the Federals.  If Hooker didn’t know where Lee was, at least he knew where Lee wasn’t.  Lee wasn’t going directly at Washington.  This at least allowed Hooker to reposition Stahel’s division.  And while the army’s commander tried to determine where Lee was going, there was enough slack to rest the footsore infantry.

In a broader context, Upperville was like a rite of passage for the Federal cavalry.  Buford said it best, referring to Gamble’s brigade after the battle, “I’ll be damned if I can’t whip a little corner of Hell with that First Brigade.”

Published by Craig Swain

"Historical marker hunter" and Civil War enthusiast.

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