One might argue that George Custer earned his brigadier’s star during the Loudoun Valley fighting, between June 17 and 21, 1863. Putting a finer point to the argument, one could say he earned the promotion on June 21, at Upperville. General Pleasonton recommended Custer for his actions at Aldie and Upperville, which would suggest the first argument to be the most accurate. However, I believe Custer’s actions at Upperville to be the deciding factor.
Why? Because I do not believe Pleasonton personally saw the fighting in which we know Custer played a role on June 17. And before the Pleasonton haters chime in with claims that he must have been hiding, a more reasonable explanation would be the exigent circumstances which forced the 1st Maine and Custer into their first charge, as well as the fact that the proper place for the corps commander at that moment in the battle was near the junction of the two turnpikes, from where he could view and direct his troops across the entire battlefield. He could not have seen the entire battlefield had he followed the 1st Maine up the Snickersville Turnpike.
Pleasonton undoubtedly did see the fighting unfold around Upperville on June 21. Not only would he have seen Custer’s actions at Upperville, but he may have personally sent him into the fray to deliver orders and to encourage decisive action. Pleasonton remained where he could observe the battle unfold and certainly watched as Custer delivered his orders and then led several of the counterattacks by the 6th Ohio and other units.
Let’s now jump ahead to July 15. Custer had been a brigadier for 17 days, when he found himself commanding the Third Cavalry Division, after Judson Kilpatrick took medical leave and went home to see his wife, who had just given birth to their first child. With Gen. David Gregg pushing his Second Division south, along a line from Shepherdstown and Charles Town, west of the Potomac and Shenandoah Rivers and the Blue Ridge, Pleasonton sent Custer to pursue into Loudoun County, east of the Blue Ridge.
What happened over the next several days is best pieced together with orders found in multiple locations, including the Official Records, the National Archives, and the Army Heritage and Education Center in Carlisle, Pennsylvania. I want to examine one very small segment of the Union advance back into Virginia.
Relying upon the Official Records, George Custer tells us, “On the morning of July 15, I assumed command of the division, which was then lying near Falling Waters. At the same time, I received orders to march my command and encamp near Berlin, [Maryland].” One might assume from Custer’s statement that he received the order to move to Berlin [Brunswick today] in the morning. But the actual order is not in the Official Records, but rather in the C. Ross Smith Papers at the Army Heritage and Education Center.
During the Gettysburg Campaign, Lt. Col. Charles Ross Smith, 6th Pennsylvania Cavalry, served as Pleasonton’s Ordnance Officer. The order to Custer did not come from Smith’s pen, however, but rather from Lt. Col. Andrew J. Alexander, Pleasonton’s Chief of Staff. Smith replaced Alexander as Chief of Staff later in the year and a large assortment of orders from Cavalry Corps Headquarters can be found in Smith’s papers.
Pleasonton’s order, written by Alexander at 8p.m., directed Custer to send one brigade across the Potomac River “at Harpers Ferry tonight and proceed down on the south side tomorrow” to a point across from Berlin. From there, Pleasonton wanted Custer to “send pickets and patrols…to a point opposite the Point of Rocks,” Maryland, from where the enemy had been firing across the river at Union supply trains, as well as elements of the Reserve Brigade. Specifically, Pleasonton wanted the officer commanding the force “to make every effort to capture or destroy” the Southerners. The corps commander ordered Custer to proceed with “the remainder of [his] command…to the vicinity of [Purcellville] taking a position on the left of the town facing [northwest].” With Union cavalry now picketing the southern bank of the Potomac, General Meade made his headquarters in Berlin for a couple days.
Colonel Alexander wrote the order at 8 p.m. We do not know when Custer received the order, but assuming he did so after midnight does not seem unreasonable, and Custer may have deemed anything after midnight as morning.
Pleasonton sent another order penned by Andrew Cohen, his Asst. Adjt. Gen, the same day, June 15, but without a time attached (published in the Official Records), in which he told Custer to send no artillery across the river and warned him that he might encounter dismounted Union cavalry.
Both orders probably reached Custer in the vicinity of Boonsboro, Maryland. Rousing his men at three a.m., June 16, Custer led the division south, passing through Rohrersville, before turning southeast to Berlin. Holding his Wolverines (his Second Brigade) near Berlin, Custer sent his First Brigade, led by Col. Othneil De Forest, back to Harpers Ferry, thus picketing a long swath of river frontage, as high water prevented him from crossing. Custer then allowed his men to unsaddle and enjoy a well-deserved rest for the remainder of the day.
Custer led the division back into Virginia on July 17 in a driving rainstorm, the First Brigade coming in from the west, across the Shenandoah River, while the Second Brigade crossed the Potomac River and entered The Old Dominion from the north. The two brigades reunited opposite Berlin and then followed the Berlin Turnpike south through Lovettsville and Wheatland to Purcellville, as he had been instructed.
Now back in the Loudoun Valley, Custer, serving as the tip of the spear east of the Blue Ridge, began screening the advance of the army. As Custer proudly told a friend, “I have had the post of honor ever since the army crossed into Virginia that is I have held the advance with my division.”
In doing so, Custer mimicked Jeb Stuart’s screening actions of three weeks earlier and sent the Fifth Michigan to secure Snicker’s Gap (Stuart had deployed Col. Thomas Munford’s brigade to hold the gap in June). By holding the gap, Custer controlled the Leesburg Turnpike, running from Winchester, through Snicker’s Gap to Purcellville, and then on to Leesburg, and Alexandria. Snicker’s Gap also controlled the Snickersville Turnpike to Aldie, Fairfax Court House, and Alexandria.
When the Wolverines arrived, they found Southern pickets from Brig. Gen. ‘Grumble’ Jones’s Brigade already in position and unwilling to retreat without a fight. Still, as one man from the regiment told his wife, “We beat the rebels soundly, took several prisoners, and chased them out of their fortifications, which we now occupy.” Jones lost at least seven men prisoners, from three regiments, at either Snickers Gap or near Purcellville June 17 and two more the following day. The Fifth Michigan held the gap through the following day, possibly supported by men from the First Vermont.
Custer let his men and horses rest on July 18. As one scribbled into his diary, “Don’t have anything to do today…A good many are writing letters as it is the first opportunity in a long time.” The feverish pace of the campaign continued to take a toll on Custer’s horses, with many going lame every day. Seeking to mitigate the problem, Custer ordered the men to get their animals reshod, and telling Pleasonton, “[I] hope soon to be ready for service.”
On the 19th, the division began moving again, with Custer moving his headquarters about ten miles southwest to Bloomfield. He sent the First Michigan to Snicker’s Gap, relieving the men of the Fifth Michigan and any men from the First Vermont. After probing west of the gap, the men of the First Michigan returned and spent the night on the mountain. The Seventh Michigan had also moved west toward the gap, while the First Vermont headed south to Ashby’s Gap.
During the day, Maj. Gen. George Meade’s Adjutant, Brig. Gen. Seth Williams issued an army circular explaining Meade’s plan for the movement of the Army of the Potomac the following day.
“The following movements of troops are ordered for tomorrow, July 20, 1863:
“The Third Corps will move promptly at 4 a.m., pass through Snickersville [Bluemont today], and take position at or in the vicinity of Upperville, on the pike from Ashby’s Gap to Aldie.
“The Second Corps will move by the direct route to Bloomfield and take position there.
“The Twelfth Corps will move to Snickersville and take position there.
“The Fifth Corps will move promptly at 4 a.m., pass through Union, and along the road to Rectortown, taking position at or in the vicinity of the point where the road to Rectortown intersects the pike from Ashby’s Gap to Aldie.
“The Reserve Artillery will follow the Fifth Corps at 10 a.m., or sooner, if the road is clear, and, after passing through Union, will be parked at the first suitable ground.
“The Sixth Corps will move at 10 a.m., follow the same route as the Fifth Corps, and halt, after crossing the Snickersville and Aldie pike.
“The First Corps will move promptly at 4 a.m., taking the route to Middleburg, leaving Philomont on the right, and will take position at or in the vicinity of Middleburg.
“The Eleventh Corps will follow the First Corps as soon as the road is clear, and take position near the crossing of Goose Creek, by the Snickersville and Aldie pike.
“Those corps the hour of march for which is not fixed will move as soon as the column in front is fully in motion. Corps commanders will keep themselves informed upon this point and will see that every effort is made to move all parts of their commands promptly and to keep the columns well closed.
“Headquarters will be established in the vicinity of Union.”
Meade’s circular is published in the Official Records. George Custer’s order to his division, in response to the directive, is in the National Archives. Writing from Bloomfield, Custer told Colonel De Forest, commanding the First Brigade, the following:
“You will picket that portion of the country lying south of the road leading from Snickersville to Upperville, beginning one mile from Bloomfield in the direction of Snickersville and continuing across the road to Union to the Upperville road one mile in advance of Bloomfield. The picket should be strongest on the road to Union. The Second Brigade (the Michigan Brigade, led by Col. Charles Town, as senior colonel), will picket that portion of the country between the mountains and the road leading from Snickersville to Upperville, connecting with the pickets of the First Brigade at the points where they picket the road from Snickersville to Upperville.
In response to Custer’s orders, the Michigan Brigade picketed the base of the Blue Ridge and men from the First, Fifth, and Sixth Michigan, aided by the Fifth New York, First Vermont and possibly the First West Virginia, seized Ashby’s Gap “after slight skirmishing,” and pushed westward, until encountering “the enemy strongly intrenched on the opposite side of the Shenandoah” River. With the gap in Union hands, the First Vermont fell back to Upperville. The Seventh Michigan remained in Upperville, probably as a reserve force should serious fighting occur in the gap.
I had, as I have unfortunately done many times, mis-filed Custer’s order when I found it about 20 years ago. Finding the order again sparked several thoughts, including Custer commanding a division just three weeks after his promotion to general, and doing so on the very battleground where he had, in my opinion, earned his star. The post also allows me to highlight accounts from civilians who watched as the Yankees again swept across their farms.
I also wanted to stress, as I have done several times in the past, the importance of the National Archives. I am very lucky to have been encouraged decades ago to not only use the archives but to become comfortable doing so, and several very close friends have facilitated my comfort level there over those decades. Importantly, my proximity to the facility has made doing so possible. Not every student of the war enjoys the same benefit.
The Official Records, to include the Supplement volumes, do not contain all the reports and correspondence generated by the armies. Rather, those volumes contain but a small sampling of what the editors thought most important to the major campaigns. Government clerks then sorted all the documents they received after the war, as they saw fit, into multiple collections or entries at the archives where they remain today. All relevant entries and microfilm collections must be searched by historians seeking to complete such a puzzle. Lastly, as I try to show here, not all army correspondence went back to the War Department and the Archives. Collections are scattered across the country. All these hurdles aside, putting the pieces back together is rewarding and often revealing.
As to my questions: Custer leading a division just three weeks after his promotion is not unique. Judson Kilpatrick had been promoted to brigadier June 13 and he received permanent command of the Third Division when Custer, Merritt, and Farnsworth received their promotions. Kilpatrick had, however, been commanding a brigade for months, prior to his promotion, as the senior colonel.
Did Custer initiate the July 19 order and the deployment of his division? My thought is that he did not. Orders filtered down from higher authority, and Meade’s circular probably went to Cavalry Corps Headquarters, where Pleasonton and his staff then prepared an order to Custer and which Custer then refined for his brigade commanders, as we see here. If I am correct, then I believe Pleasonton’s order remains to be found.
Let’s spend a minute looking at Custer’s deployment and examining any correlation to the events that transpired over the same ground in mid-June? To make an infantry comparison from later in the war, what Custer did was to reverse Jeb Stuart’s trenches (though Stuart did not actually dig trenches in June). In other words, where Stuart deployed his men facing east to hold the Federals out of the Shenandoah Valley, Custer deployed his troops facing west to contain the Southerners within the Shenandoah Valley and out of the Loudoun Valley. And he did so by employing many of the same terrain features and road networks used by Stuart.
Most importantly, Custer took advantage of the gaps in the Blue Ridge, immediately sending men to seize and hold Snicker’s Gap and thus taking control of the Leesburg Turnpike, and the Snickersville Turnpike. Then, as the army moved farther south into the Loudoun Valley, Custer shifted his focus to Ashby’s Gap and the Ashby’s Gap/Little River Turnpike. In other words, Custer did what Stuart would have done but for the fighting of mid-June and the subsequent decision to send Stuart on his controversial Ride to Gettysburg. Custer successively blocked the gaps as he proceeded south ahead of the army, as Stuart would have done moving north.
Custer could afford to pull his men from the gaps, except for pickets, as Meade’s infantry moved into the same area. For instance, he could pull his men from Snicker’s Gap once the Twelfth Corps arrived and took “position there.” Likewise, he could move his men south of Ashby’s Gap once the Third Corps arrived and assumed responsibility for the gap.
The towns of Bloomfield and Union (Unison today) became important as they are midway between Snicker’s Gap and Ashby’s Gap and control a road network eastward, as well as connecting the Snickersville and Ashby’s Gap/Little River Turnpikes. Specifically, Custer instructed De Forest to place his strongest force “on the road to Union.” Stuart had done much the same thing when he deployed Brig. Gen. William “Grumble” Jones’s Brigade at Union and Col. John Chambliss’s Brigade nearby. Why? Because the town controlled several roads. As a final measure, Custer deployed pickets between the Blue Ridge and the north/south roads immediately east of the Blue Ridge, that being the Trappe Road and what is today the Ridgeside and Foggy Bottom Roads.

Another reason to concentrate a large force around Union is revealed in the last line of the circular – Meade planned to make his headquarters there.
When all his army had taken position, Meade had, not only blocked access into the Loudoun Valley from the Shenandoah Valley but he had also blocked access from the Loudoun Valley through Bull Run Mountain to points east, and he had done so in depth with his entire army, a benefit Stuart had not enjoyed.

Lastly, what of the civilians in the Loudoun Valley? I introduce all three of the women quoted here in my book. All were staunch Southerners. Amanda Edmonds, the youngest of the three and possibly the most outspoken, lived along the Blue Ridge just south of Ashby’s Gap. Her family home saw a steady stream of Confederate soldiers and from them she learned on July 18 that Yankees had occupied Snicker’s Gap. “I suppose the next move will be to take Ashby’s. O! hour of horrors!
The following day she wrote, “Our indefatigable friends, the blue devils, arrived in Upperville this evening.” On July 20, she explained, “About ten o’clock the blue jackets advanced to the Gap…one Yank killed in the village. They halt a long time and then advance to the desired Gap without further resistance, as the Confederates have fallen back…much sauce characterizes the Yanks.” The next day, she watched, with her family, as the soldiers searched their home.
At Oakley, southeast of Upperville, Ida Dulany, whose near minute by minute account of the June 21 fighting is so helpful to our understanding of the battle, maintained a very spotty diary through July. On July 18, as the Yankees pressed southward into the Loudoun Valley she learned, in ever increasing detail, of the disaster in Pennsylvania. “We have had very dark days before, but this is the darkest we have known…” As she had in June, she faced the occupation by the Yankees without her husband at home.
In an undated entry in July, she writes, “I do not know the day of the month or the day of the week, or anything else scarcely, so worried and worn out have I been for the last three or four days.” Her statement suggests to me that she is writing about July 21 or 22. “We are completely surrounded by Yankees, the camp being in the field before the house. As the General has issued orders that the men must take everything, everything is taken. All our hogs, our little beeves, and…all our milch cows” were taken. One wonders how many animals she had been able to save from the enemy in June or how many she and her husband had acquired in the several weeks since June 22, when the Federals had moved back to Aldie?
Mrs. Dulany’s mention of “the General,” is certainly curious, especially as we focus on Custer. Did she refer to Custer? A trooper in the Seventh Michigan noted in his diary on June 20, “I am detailed for corporal of the guard at Head Quarters at [Oakley]…” Does he refer to division headquarters or regimental headquarters? The same trooper writes the next day, “The boys go foraging to bring in sheep & chickens by the wholesale. The people are all secesh in these parts so the Yankees draw on them rather hard.”
Mrs. Dulany then writes, “Col. Mann and his staff have this house as headquarters, which protects the interior, but outside everything is going. We will be left to live on wheat bread and water, but we hope for better days.” She refers to Col. William Mann, commander of the Seventh Michigan. I write of Mann extensively in my book Chasing Jeb Stuart and John Mosby, and I have also written an article about him for Gettysburg Magazine, titled “‘It is horrible to have such a man in command of a Michigan Regiment:’ Col. William Mann and the 7th Michigan Cavalry During the Gettysburg Campaign.” Mann was a bit of an imperious young officer with a high opinion of himself, and who became rather infamous in the decades after the war, when he accrued and lost several fortunes, and became involved in several scandals. I suspect he might have enjoyed his men and others referring to him as “General.” After occupying a home in Bloomfield, Custer did move his headquarters to Upperville on July 22, though I do not know where he raised his flag. Doing so brought him across the area, where he had earned his star. Additionally, several infantry generals might have made their headquarters on Mrs. Dulany’s property.
Edwin and Catherine Broun owned a store in Middleburg and split their time between their home adjacent to the store and their farm outside of town. Like Ida Dulany’s diary, Broun’s diary is spotty at times, to include the summer of 1863, but she writes extensively on July 23 and 24, noting on the 23rd, “We are again surrounded by Yanks.” Specifically, she identifies the Thirty-Ninth Massachusetts Infantry and Maj. Gen. John Newton as being on her property. Newton commanded the First Army Corps and the Thirty-Ninth Massachusetts had been attached to his corps during the retreat from Gettysburg. And we see from General Meade’s circular, “The First Corps will… take position at or in the vicinity of Middleburg.”
On July 22, Meade’s adjutant issued a new circular, detailing the routes by which the army would resume its march south. The order concluded, “Headquarters of the army will be moved to Upperville, on the Ashby and Aldie pike.” Other accounts, however, suggest that Meade made his headquarters farther south, along the Manassas Gap Railroad.
Sources:
Documents from the National Archives
The C. Ross Smith Papers, Army Heritage and Education Center
Victor Comte Letters, University of Michigan
John Morey Diary, University of Michigan
Burlington Weekly Free Press
Boudrye, Historic Records of the Fifth New York Cavalry
Gracey, Annals of the Sixth Pennsylvania Cavalry
Lawrence, Dark Days in Our Beloved Country, The Civil War Diary of Catherine Hopkins Broun
Lawrence, editor, Society of Rebels, Diary of Amanda Edmonds
Mackall, Meserve, and Sasscer, editors, In the Shadow of the Enemy, The Civil War Journal of Ida Powell Dulany
Meade, The Life and Letters of General George Gordon Meade
Merington, editor, The Custer Story
Sparks, Inside Lincoln’s Army
Wert, The Controversial Life of George Armstrong Custer
What an extremely interesting article, Bob! As I have said to you before, you must’ve been some police officer. You can dig up better evidence than anybody I know of. Right now all I have had time to do is read it at face value. Soon I hope to digest it more deeply with the maps.
I will print this off and coil bind it to add to my Custer collection.
Thanks so very much for this.
Tom
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It is interesting how closely this movement mimics the movement of the cavalry into Loudoun and Fauquier County in the fall of 1862.
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I completely agree, Sharon. The actions in the Loudoun Valley would make a great staff ride topic.
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Yes it would! I have a friend who grew up there so we have wandered around a bit following the cavalry from where they crossed the Potomac at Berlin (Brunswick) down through Barbee’s Crossroads (Hume) and down past Orlean to Waterloo Bridge.
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Thanks for another great post to help me better understand Loudoun Valley cavalry actions. I’m Ida Dulany’s 3x great-grandson. I have images of her original diary from the VMHC. For the undated entry in July, Ida wrote what looks like a number 7 above the word July. Perhaps she started to write a date and then realized she had no idea of the date, so she stopped. That’s just a guess. I had no idea until reading this post that Custer could have had his headquarters at Oakley, but it makes perfect sense. Also, in Ida’s undated July entry, she refers to her Uncle Nathan and his losses in and out of the house. Uncle Nathan is Nathan Loughborough. He owned Rokeby, the property south of Oakley. I wonder which officer headquartered there, if any. Thanks again for the post.
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Thank you for this information. I have followed your own page for a couple of years and appreciate your work. It would be wonderful if more of her diary turned up one day, though I’m grateful for what survives. She was a terrific observer of events around her and her June 21 entries are indispensable.
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Thank you. I recently started a new website for my project researching the enslaved community at Oakley. Here is the link: https://enslavedatoakley.com/ I am always on the lookout for other pieces of the diary. Finding a cousin only five years ago who had the Dulany family bible from Oakley is an excellent illustration of why it’s so important to ask other relatives, sometimes distantly related relatives, if they still have something hidden away in their attic.
– Joseph Roby
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Thank you for the link to your new site, Joseph. I look forward to reading through it. And continued good luck in your search and your work.
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