Upperville

Drama at Vineyard Hill

— Gettysburg Campaign —

Photographed 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

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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 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.

[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.

Erected by Virginia Civil War Trails.

Topics and series. This historical marker is listed in this topic list: War, US Civil. In addition, it is included

Upperville Park image. Click for full size.

Photographed by Craig Swain, June 22, 2007

2. Upperville Park

The marker sits between the baseball fields and the highway on the crest of Vineyard Hill.

in the Virginia Civil War Trails series list. A significant historical month for this entry is June 1863.

Location. This marker has been replaced by another marker nearby. It was located near 38° 59.432′ N, 77° 52.332′ W. Marker was in Upperville, Virginia, in Fauquier County. It was on John S. Mosby Highway (U.S. 50) west of Dunvegan Drive, on the right when traveling east. The marker on Vineyard Hill, in Upperville Park. The park is located across the highway from Ivy Hill Cemetery. Touch for map. Marker was at or near this postal address: 8585 John S Mosby Hwy, Upperville VA 20184, United States of America. Touch for directions.

Regionally, this marker was in the Washington Metropolitan Area

and in Northern Virginia.

It was also in the American South,

specifically in the Upper South,

and in the Mid-Atlantic.

Globally, it was in North America,

the Western Hemisphere,

the Western World,

and the Anglosphere.

Historically, it found itself in what was once the territory of the Mississippian Culture,

one of the original Thirteen Colonies,

one of the Confederate States of America,

and the Antebellum South.

Other nearby markers. At least

View From Vineyard Hill image. Click for full size.

Photographed by Craig Swain, February 5, 2007

3. 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.

8 other markers are within walking distance of this location: Battle of Unison (here, next to this marker); a different marker also named Upperville (here, next to this marker); The Smith House (approx. ¼ mile away); The Gibson House (approx. 0.4 miles away); The Armistead House (approx. half a mile away); The Upperville Library (approx. half a mile away); This Stone (approx. 0.6 miles away); Mary Elizabeth Conover Mellon (approx. 0.6 miles away). Touch for a list and map of all markers in Upperville.

Another marker is no longer nearby. Battle of Unison (was here, next to this marker but has been permanently removed).

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

Site of Trappe Road Fighting image. Click for full size.

Photographed by Craig Swain, June 22, 2007

4. 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.

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 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. The Battles of Aldie, Middleburg and Upperville. American Battlefield Trust website entry (Submitted on April 19, 2024, by Larry Gertner of New York, New York.)

2. Battle of Aldie. (Submitted on June 30, 2007, by Craig Swain of Leesburg, Virginia.)
3. Battle of Middleburg. (Submitted on June 30, 2007, by Craig Swain of Leesburg, Virginia.)
4. Goose Creek Bridge.

Country Lane in Battle Area image. Click for full size.

Photographed by Craig Swain, June 22, 2007

5. 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.

(Submitted on June 30, 2007, by Craig Swain of Leesburg, Virginia.)
5. Haymarket. (Submitted on June 30, 2007, by Craig Swain of Leesburg, Virginia.)

Additional keywords. Gettysburg Campaign

Blakely Grove School image. Click for full size.

Photographed by Craig Swain, June 22, 2007

6. 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 was last revised on October 25, 2026. It was originally submitted on June 30, 2007, by Craig Swain of Leesburg, Virginia. This page has been viewed 3,917 times since then and 123 times this year. Last updated on July 4, 2007, by Craig Swain of Leesburg, Virginia. Photos: 1, 2, 3, 4, 5, 6. submitted on June 30, 2007, by Craig Swain of Leesburg, Virginia. • J. J. Prats was the editor who published this page.