“Bite-Size Bits of Local, National, and Global History”
“Bite-Size Bits of Local, National, and Global History”
Upperville in Fauquier County, Virginia — The American South (Mid-Atlantic)


Drama at Vineyard Hill


—Gettysburg Campaign —

Upperville – Drama at Vineyard Hill Marker Photo, Click for full size
By Craig Swain, February 5, 2007
1. Upperville – Drama at Vineyard Hill Marker
Inscription. This site, known during the war as Vineyard Hill, commands a clear view of the road, stone walls, and fields in front of you where 10,000 cavalry and infantry clashed in the Battle of Upperville on June 21, 1863. It was the fifth day of attack and counterattack along present-day U.S. Route 50 and in the towns of Aldie, Middleburg, and Upperville. Union Gen. Alfred E. Pleasonton pushed west towards the Blue Ridge Mountains while Confederate Gen. J.E.B. Stuart fought to delay the Northerners long enough to conceal Gen. Robert E. Lee’s march through the Shenandoah Valley toward Pennsylvania.

The Battle of Upperville was the largest of these engagements, and the most dramatic aspects of that encounter took place at Vineyard Hill. From here Stuart fought to prevent the Federals from seizing the village of Upperville behind you and the critical intersection at Ashby’s Gap Turnpike (Route 50) and Trappe Road, to allow his embattled forces to reach the safety of the Blue Ridge Mountains at Ashby’s Gap.

Here Stuart directed two of his brigades as they resisted the advance of three Federal brigades. The fighting near here was desperate and often hand-to-hand, the men wielding sabers and pistols. As Stuart’s line gave way on the left, he rode among his troopers restoring order and fighting “with the men like a common
Close Up of the Waud Illustration Photo, Click for full size
By Craig Swain, February 5, 2007
2. Close Up of the Waud Illustration
soldier.” Charge and countercharge carried the men and horses back and forth across these fields under the deadly fire of artillery.

Less than a mile to your left, and visible to the men on the high ground around Vineyard Hill, four other brigades clashed, leading one Federal participant to conclude, “the panorama was one of the finest and most animating ever beheld.” Once the Confederates extracted themselves there and reached Ashby’s Gap Turnpike, Stuart ordered the last of his men to retire from Vineyard Hill.
Erected by Civil War Trails.
Marker series. This marker is included in the Virginia Civil War Trails marker series.
Location. 38° 59.432′ N, 77° 52.332′ W. Marker is in Upperville, Virginia, in Fauquier County. Marker is on John S. Mosby Highway (U.S. 50), on the right when traveling east. Click for map. The marker on Vineyard Hill, in Upperville Park. The park is located across the highway from Ivy Hill Cemetery. Marker is in this post office area: Upperville VA 20184, United States of America.
Other nearby markers. At least 8 other markers are within 4 miles of this marker, measured as the crow flies. Battle of Unison (here, next to this marker); Lee Moves North Again (approx. 1.1 miles away); Battle of Upperville
Upperville Park Photo, Click for full size
By Craig Swain, June 22, 2007
3. Upperville Park
The marker sits between the baseball fields and the highway on the crest of Vineyard Hill.
(approx. 1.1 miles away); a different marker also named Battle of Upperville (approx. 1.4 miles away); Attack at Goose Creek Bridge (approx. 2.8 miles away); Rector House (approx. 3.6 miles away); Rector’s Crossroads (approx. 3.6 miles away); Mosby’s Rangers (approx. 3.7 miles away). Click for a list of all markers in Upperville.
More about this marker. Marker features a newspaper illustration with the caption, “A sketch by A.R. Waud for Harper’s Weekly illustrates the Battle of Upperville on June 21, 1863, with Union cannon in the foreground and Ashby’s Gap in the distance. The square enclosure in the upper left center is Vineyard Hill where you now stand.”
Regarding Upperville. As discussed on the marker, Upperville was the culminating battle in a series fought along the historical Ashby’s Gap Turnpike, which is present day John S. Mosby Highway (U.S. 50). The campaign can be traced by visiting several markers along the route. The fighting began at Aldie on June 17 (see link 1) and spilled into Middleburg. On June 19, Stuart’s cavalry was driven
View From Vineyard Hill Photo, Click for full size
By Craig Swain, February 5, 2007
4. View From Vineyard Hill
Looking East, the Federal cavalry was positioned on the far edge of the open ground, with both sides contesting the intervening hills and pastures. This view is nearly a direct opposite line from that of Waud's drawing.
out (see link 2). Next both sides contested the bridge at Goose Creek (see link 3) on June 21. After fighting at Upperville, Stuart defended Ashby’s Gap for a short time, but determined to skirt around the Union Army moving to Haymarket (see link 4). As result, the cavalry of the Army of Northern Virginia began the Gettysburg campaign out of position to support the main army moving into Pennsylvania.
Related markers. Click here for a list of markers that are related to this marker. To better understand the relationship, study each marker in the order shown.
Also see . . .
1. Battle of Aldie. (Submitted on June 30, 2007, by Craig Swain of Leesburg, Virginia.)
2. Battle of Middleburg. (Submitted on June 30, 2007, by Craig Swain of Leesburg, Virginia.)
3. Goose Creek Bridge. (Submitted on June 30, 2007, by Craig Swain of Leesburg, Virginia.)
4. Haymarket. (Submitted on June 30, 2007, by Craig Swain of Leesburg, Virginia.)
5. Aldie, Middleburg, and Upperville Battles. Detailed information about the battle at Upperville, along with the other battles fought nearby. (Submitted on June 30, 2007, by Craig Swain of Leesburg, Virginia.) 
Additional keywords. Gettysburg Campaign
Categories. War, US Civil
Site of Trappe Road Fighting Photo, Click for full size
By Craig Swain, June 22, 2007
5. Site of Trappe Road Fighting
Here some of the most savage fighting of the day occurred. Trappe Road runs North off the highway approximately 1.2 miles West of Vineyard Hill.
Country Lane in Battle Area Photo, Click for full size
By Craig Swain, June 22, 2007
6. Country Lane in Battle Area
Typical of the roads around the battle area, the stone walls served to funnel movement and offer ready built defensive works. This particular stretch of the Millville Road saw much use by the Confederates while positioning to meet Federal advances.
Blakely Grove School Photo, Click for full size
By Craig Swain, June 22, 2007
7. Blakely Grove School
One of many structures dating back to the time of the battle which still dot the landscape. Gen. Buford's division passed here while moving into the fight along the Trappe Road.
Credits. This page originally submitted on , by Craig Swain of Leesburg, Virginia. This page has been viewed 1,932 times since then. Last updated on , by Craig Swain of Leesburg, Virginia. Photos:   1, 2, 3, 4, 5, 6, 7. submitted on , by Craig Swain of Leesburg, Virginia. • J. J. Prats was the editor who published this page. This page was last revised on June 16, 2016.
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