1863-65: Theodore Frelinghuysen Vaill Letters

1st Lt & Adjutant Theodore F. Vaill

In 1868, Theodore Frelinghuysen Vaill (1832-1875) published the regimental history of the 2nd Connecticut Volunteer Heavy Artillery which was originally organized as the 19th Connecticut Volunteer Infantry. He served with the regiment as a private from 1862 to September 1863 when he was made a sergeant. He was promoted in March 1864 to 1st Lieutenant as Adjutant. He was mustered out of service on 18 August 1865 at Fort Ethan Allen in Washington D. C.

Theodore was the son of Rev. Herman Landon Vaill (1794-1870) and Flora Gold (1799-1883) of Litchfield, Connecticut. His siblings included Catharine Harriet Gold Vaill (1824-1898), Charles Benjamin Vaill (1826-1881), Elizabeth Sedgwick Vaill (1828-1909), Abbie Everest Vaill (1829-1897), George Lyman Vaill (1831-1833), Sarah Hopkins Vaill (1834-1862), Clarissa Champlin Vaill (b. 1836), Joseph Herman Vaill (1837-1915), Julia Maria Vaill (1839-1912), and Mary Woolsey Vaill (1842-1871).

Theodore was an 1858 graduate of Union College. He married Alice Mercy Dudley (1842-1920) after the war, published the afore-mentioned regimental history, and served as the editor of the Winsted Herald until his premature death in 1875 at the age of 43. He is buried in the Winsted Old Burying Ground in Winsted, Litchfield county, Connecticut.

Theodore was wounded in the fighting at Fort Fisher — a mere flesh wound in the left hip by a “cast iron ball from spherical case shot.”


This letter was written a couple of weeks before the 19th Connecticut Infantry was broken up into separate garrisons. Companies B, F, and G went to Fort Ellsworth, Company A to Redoubt A, Company D to Redoubt B, Companies C and K to Redoubt C, and Companies E, H, & I to Redoubt D.  These were small works in the vicinity of Fort Lyon on the Mount Vernon Road that commanded the land and water approaches to Alexandria on the south. It wasn’t until 23 November 1863 that the 19th Connecticut was redesignated the 2nd Connecticut Heavy Artillery.


Addressed to Miss Mary W. Vaill, Litchfield, Connecticut

Headquarters 19th Connecticut Volunteers
Ft. Worth, Virginia
April 25th 1863
Saturday 2 P.M.

Dear Father,

Yours of the 23rd, with Joe’s & Mary’s, are just received, & I am glad to hear so particularly bout farm matters. If Joe will keep a sort of farm journal, entering the outlines of the work done each day or week therein, & send to these Headquarters, I think I could help to supervise matters, or at least could render the aid of my valuable counsel. I think it will be much the better way to mow the whole from the West Orchard clear down to the hen house, even if it yields but little, for it will save fencing, & after haying & harvesting, the whole can be used for pasture.

I suppose Kent is going to seed down the lot north of John’s. It ought to be, by all means. You say nothing about the stony pasture & south acre lot. What are you going to do with them? If oats are sowed there, I hope that also will be seeded down. And are you going to mow the two-acre lot over south? I want to know the whole program.

It is clear as a bell today but the northwest wind blows like 60. We shall try to send something for the library meeting. No news here. I suppose you will see Charley Deming now home on a furlough. He told me he should trout some. In haste, your affectionate son, — T. F. Vaill

Dear Joe,

I guess you won’t complain of my not writing to you now-a-days. When the east side of the Pond Lot is sown to grass, I hope you will see that the stones are completely got off (all but that ledge) & that it is laid down smith enough for a mowing machine. But what is to be done with the rest of the Pond Lot where Kent had oats? If you put oats there & seed it down, you ought to put on some manure or you will have small oats. I would  not attempt any corn except what Hull takes, even if you should be at home. There is too much ground broken up now — (I didn’t calculate on going to war) & you had better get oats in & let corn go. Hire team & plow for oats (at least I should). The strong pasture, South acre, Pond Lot, north of barn, & where Kent had corn over east, & seed it all down. It will make an enormous plowing job & a large harvesting, but if you don’t have to fuss & worry & replant & scare crows, & hoe, hoe, hoe, plant, plant plant, all the spring, you can do a big thing with oats, & they are a reasonably sure crop. This is my advice on account of your weak-handedness.

I wish you would not drive Jennie every day. Before you know it, she will be a good for nothing female Peg. with neither strength nor ambition nor looks nor value. Isn’t there a certain dray that needs drawing out?

There is a rumor here that Charley Vaill is to be appointed Asst. Surgeon to the 19th [Connecticut]? Is it so? I hope so. The authorities have got on the scent of several deserters from the 19th now in Kent, Winsted, &c. & before they know it, they will be nabbed & made to come to “time.”

Write at once, Your brother, — Faydo

Dear Mary,

Your little teenty taunty letter, at the end of Pa’s & Joe’s was like a delicious dessert. I roamed, enchanted, through that desert, and now I wish you would “do so some more.” Whenever Joe writes to me, put in a word, & I’ll give you some revenge. Charley Hinsdale says that Nealie is delicious & the boys plague me about her almost to death. Ole Dr. Allen & his lovely wife & beautious sister-in-law still rusticating at the more depressed extremity of the smiling plain? In other words, is Mary Bissell to home?

You must not be so sanguinary concerning my promotion. “Bangers still lives.” (Shakespeare) “Deming exists.” (Vaill).  Besides, my ambition is reached, in the military line, & I shall be perfectly satisfied to remain where I am until the end of the war. Indeed, I would not accept any other office, short of a commish — and for that to fish, I have no disposish.

I am now in a situation where I can read & write as much as I please & there are hundreds of men in the regiment who would think themselves fortunate if they were in it. How is Ellen Peck? & all the young folks? Why don’t you tell me something about them?

We shall send something to the Library Meeting. I hope Joe will be so fortunate as to stay at home where he can recover & do some good & tell him to remember that that Jennie is not yet 4 years old & that a horse is much easier injured that cured. Please write me soon if you will. I will send that blackberry jam immediately. — Tedo


In this lengthy and descriptive letter to his father, Theodore shares his views on the progress of the war and why he has come to believe that the demise of the Confederacy is inevitable. He also relates a tale told to him by a friend assigned to accompany conscripts from New Haven to the battlefront in Virginia. His friend, it seems, was compelled to shoot and kill a substitute who jumped overboard from a transport steamer in the East River in an effort to escape service.


Addressed to Rev. H. L. Vail, Litchfield, Conn
Postmarked Alexandria, Va.

Headquarters 19th Connecticut Volunteers
Near Fort Lyon, Va.
Monday morning, August 11th 1863

Dear Father,

Rev. Herman L. Vaill (ca. 1845)

Your note of the 8th was yesterday received. as to Irving’s going away, I am aware it must make you some inconvenience just now. But as you are done with him, I hope you will stay done with him. As you say, there will doubtless be help to be got before long & even if everything is not got in in first rate time & order, you can manage to get along somehow. When I enlisted, I hoped to get through the war so as to be home this summer, but it seems I miscalculated. But now I think there is good reason for believing that we shall be on hand next summer to help in haying & hoeing & planting.

Since the fall of Vicksburg & the retreat of Lee, the belief has taken hold of the Southern people that their undertaking is to fail & that belief is daily weakening them at every point. The Government evidently does not intend to push operations at present, except to watch Lee, organize negro regiments, enforce the draft, & pound away at Charleston. And we believe that this course is all that is necessary — for the effect of recent events will daily weaken the rebels until they meet with a success somewhere & I don’t see where they are going to find it. Charleston will probably fall by the 20th of October if not sooner & then the rebellion will cave right in — perhaps more suddenly than anybody thinks for.

The hold that we have on their chief city, New Orleans, which they cannot shake off — the possession of the entire Mississippi — the vast number of prisoners & spoils in our hands — their failure to occupy a single foot of free soil — the miserable failure of Lee’s & Morgan’s invasions & the New York riots (which were all parts of one plan) — the result of the election in Kentucky — the failure of “Recognition & Intervention” [by England] — the depreciation of Confederate money — the uprising & unmistakable popular discontent in North Carolina & Mississippi — our superiority on the water — and lastly, the purpose of the government to arm, use, and protect negro troops — these are the reasons for the faith which is in me that the war will very soon be over & the rebellion utterly wiped out. I hope the government will pay all its attention to Charleston & take it if it costs a thousand millions & a hundred ironclads — for with its fall comes the speedy end — so I think.

George Mason popped in on us yesterday morning & staid two hours. He is going with 150 substitutes to report to the 14th Connecticut. All of them are substitutes except 2 or 3 & the worst set of men out of the infernal regions. Mason says they all intend to run away & have to be watched every instant. When the boat was coming down the East River & was about 30 rods from “Corlear’s Hook,” one of them jumped overboard & struck out for New York.¹ He was shot at several times but Mason had the honor of putting a ball through him. It went in between his shoulder blades & came out of his breast. A boat was lowered & he was picked up & taken to hospital in New York where he probably soon died. They are New York roughs & rioters & are carrying on their infernal substitute business on a grand scale. Mason has gone to Warrenton & will return to New Haven.

We have the hottest weather I ever saw now-a-days. It is now but 8 A.M. & the mercury is 96° in the shade & will be 106° by noon. It has been 105° every day for a week past. All the boys are well except Charley Adams. ² He is sick with bowel complaint in hospital at Fort DeKalb opposite Washington. Not how sick, I don’t know.

Please write immediately & let the rest do likewise, With love. In haste, — Theodore


¹ These substitutes may have been the ones transported from New Haven to Washington D. C. aboard the steamer “Continental” that were destined to join the 14th Connecticut at Warrenton, Virginia.

² Charles G. Adams (1845-1864), the son of Charles and Julia Hinman Adams, enlisted in Co. C, 19th Regiment Connecticut Volunteers, in 1862 following the outbreak of the Civil War. On June 11, 1864, he died of wounds received on June 1 during the Battle of Cold Harbor. During the war, Adams regularly wrote letters to his parents and sisters. His letters are housed at the Litchfield Historical Society [Adams family collection, 1798-1928]


In this letter to his sister, Mary Woolsey Vaill (1842-1871) , Theodore tells his sister that the substitutes coming to Connecticut regiments positioned in Virginia are almost exclusively substitutes who are “the worse set of men alive” according to their mutual friend George Mason.


Addressed to Miss Mary W. Vaill, Washington, Connecticut

Headquarters 19th Connecticut Vols.
Near Ft. Lyon, Va.
August 14th, 1863

My Dear Sister Mary,

The suspenders came safely by mail yesterday and now they adorn my beautiful shoulders. I received (also by mail) a magnificent pair of slippers last Monday — the gift of abbie or Julia, or you, I don’t know which. But they are (in the chaste language of the volatile Leavitt) “awful nice,” and I am very much obliged to mu friends and blood relatives for them.

Deacon Adams arrived here last night direct from Litchfield. He came to see Charley [Adams] who is sick in the hospital at Arlington with summer complaint & debility, but is getting better. The deacon saw Julia (Vaill) just before he started & said she was looking quite well.

George Mason has been down here from New Haven with 160 men assigned to the 14th Connecticut near Catlett’s Station. They were taken out there & George stopped here night before last on his way back to New Haven. He says 2 or 3 of these 160 were drafted men & the rest substitutes & that they were the worse set of men alive. Many of them were New York rioters who sell themselves, then desert & sell again if they can. George shot & killed one of them who jumped overboard & attempted to swim in New York when they were coming down the East River. Many people think that these men will not be worth anything as soldiers but we know better. They have voluntarily become soldiers for pay & there is a way to bring them to the scratch & keep them there. If they were to be caught, they would be shot dead.

But the mail is going this instant. The carrier is waiting for me. I received your former letter & will reply soon. I thought Fanny was going to write to me. I wish she would & I would reply to you both together.

In haste. With much love, — Theodore


Though Theodore addressed this letter to his father, he intended it primarily for the parents of William (“Willie”) H. Plumb who were farmers near Litchfield, Connecticut. He wished to make it known to them that Willie was seriously ill and in the hospital on Seminary Hill overlooking Alexandria. The hospital was in the home of Bishop James, otherwise known as “Malvern.”


Headquarters 19th Connecticut Vols.
Near Ft. Lyon, Virginia
Saturday evening, Aug. 29th, 1863

Dear Father,

I have lately received letters from Charles, Joe, Em and Mary but have not heard directly from home in some time. Sergt. Dwight Kilbourn arrived here today from Litchfield and reports that he saw Joe there last Tuesday or Wednesday.

I sent a letter to Charles yesterday & told him to forward it to Litchfield and it may be that you have not yet received it. In it I stated that Willie Plumb ¹ had just arrived but was very far from well. He took no nourishment of any account from the time of his leaving Bedlow’s Island until he arrived here, except a little whiskey and was taken to the hospital the day after he got here and has rapidly grown worse. This morning he sent over to have us come and see him, and Goodwin [Osborne], Lewis Bissell, and I went. We found him in a very critical condition. He has the typhoid fever and this, added to his chronic diarrhea, and his general debility, render his case unusually dangerous. They have had men there as sick with Typhoid Fever as Willie is who have recovered, but they have had constitutions to fall back upon which Willie has not. He does not suffer much and inclines to sleep and doze a great deal — and ate a little today. He told me this afternoon to write and tell his people not to be alarmed about him and that he was confident that he should be better soon. But we think it is very doubtful.

Henry Plumb, Surgeon 19th Connecticut

Please communicate the substance of this letter to Mr. Plumb’s people & tell them that they may be assured that Willie is being as well cared for as he could be anywhere. Our hospital is a mile & a half from here in a spacious home in the most beautiful situation that is anywhere around here. Dr. Plumb is there himself & the nurses are as kind and attentive as anybody could be. I know, for I was there when I got hurt some time ago and the indifference which is generally observed in hospitals on the part of nurses & physicians & cooks is never seen there. ²

Sunday morning, August 30th.

I have not heard from Willie this morning but the mail leaves soon & I will send this letter — and I shall write again this afternoon. Dwight Stone is going over to the hospital this morning. I received a letter yesterday from Ed & Seth [Plumb] ³ & shall write them today. They are at “South Mills, North Carolina” — a small settlement a few miles south of the Va. & N. C. state line, 30 miles from Norfolk & 13 from Elizabeth City.

In haste. Your affectionate son, — Theodore F. Vaill

N. B. This letter is intended, as you see, for the Plumb’s, and you will please lose no time in giving it to them. I thought that by writing to you, it would be more likely to be taken directly from the office.

P. S. 9 A.M. Sunday morning. A man just from the hospital says that Willie is just about the same as he was last night.


¹ “Willie” was William H. Plumb (b. 1840) who served with Vaill in the 19th Connecticut. He survived the war and mustered out with the regiment in July 1865.

² The hospital was described by Edward Williams Marsh, a member of the 19th Connecticut, as follows: “The hospital was in the house owned and occupied by Bishop John or St. John [John Johns] of the Episcopal Church of Virginia. It was a fine roomy mansion, well situated on a rise of land that overlooked Alexandria and the Potomac, the capitol at Washington being plainly visible.” The home — named “Malvern” — was on Seminary Hill, near the intersection of Quaker Lane and Seminary Road. Henry Plumb (1836-1929) was the Surgeon of the 19th Connecticut. [See — Sarah Eugenia (Tolles) Plumb to Walter F. Tolles]

³ Lt. Seth F. Plumb (1836-1864) served in Co. E, 8th Connecticut Infantry. He was killed at the Battle of Chapin’s Farm, Virginia, on 29 September 1864.


Theodore wrote this letter to his sister, Abbie Everest Vaill (1829-1897), from the headquarters of the 19th Connecticut near Fort Lyon (near Alexandria, Virginia). The envelope associated with this letter dates from May 1863 so it could not be the original envelope that this letter was sent in. 


Addressed to Rev. H. L. Vaill, Litchfield, Conn.
[Note: Letter & envelope are not matched]

Headquarters 19th Connecticut Volunteers
Near Fort Lyon, Va.
September 16th 1863

Dear Sister Abbie,

Your note of the 10th arrived here probably on the 12th but I did not get it until yesterday. I have just returned from a five days’ pass to Washington & the forts on this side of the river — this being the first time I have ever been out of camp (except one) since we left Litchfield. But I have very little time this morning & must be short.

As to [my horse] Jennie, sell her if you can. I perfectly agree with you that it is not best to winter a horse that is not wanted & it is not best to wait for a great price either. If you want to sell her, take the first good opportunity & if you can’t get $100, take $90. Horses can be got in the spring at any price from 25¢ to $1,000.

Willie Plumb remains about the same. 3 of our companies have been ordered to Occoquan in pursuit of guerrillas & went yesterday morning. Ed[ward F.] Gold’s Company [G] is one of them. Occoquan is about 17 miles from here & guerrillas are constantly stealing horses & committing other depredations.

I enclose my order for the 4th payment of $10 due me from the state. You will please pass the amount to my credit & acknowledge the receipt thereof soon.

In haste. Your affectionate brother, — T. F. Vaill

aacivvail6 - Version 2


In this letter to his father, Theodore describes his added duties as the adjutant of the regiment that are above and beyond those he has to perform as the Sergeant-Major. He also informs his father that the 19th Connecticut has now been re-designated the 2nd Connecticut Volunteer Artillery (C. V. A.).


Addressed to Rev. H. L. Vaill, Litchfield, Conn.

Headquarters 2nd C. V. A. [Connecticut Volunteer Artillery]
Near Fort Ellsworth, Virginia
December 11th 1863

Dear Father,

Yours of the 7th was received yesterday. I was aware that I was owing you a letter, but I am uncommonly busy now-a-days and have hardly had time to write a letter in three weeks. Although I am Sergt. Major, I have all the Adjutant’s work to do (or at least I have all the responsibility & supervision of the Adjutant’s Office) besides my own duties. (The reason why I am depended on in the adjutant’s Office us that the Adjutant don’t know enough to run his machine & never will.) Then we have a Brigade Drill once a week and a Battalion Drill four times a week and other doings that keep me busy.

I called to see Willie [Plumb] last night. He walked about ¼ of a mile yesterday for the first time. I wrote a long letter of thanks to Becky Osborne some time ago, but I infer from your note that she has not received it. I will write to the rest of the contributors  to my box soon. One reason why I have not written is that I was waiting to hear from [my brother] Joe. Where is he & is he going to his regiment or not?

I send you herewith the 2nd Vol. of the Gospel according to Lt. Benjamin by William Allen Butler, author of nothing to wear. It is first rate reading.

We have received our new designation from Gov. Buckingham & are henceforth the “Second Connecticut Artillery.” My address therefore is “Sergt. Maj. T. F. Vaill, 2nd C. V. A., Alexandria, Va.

But I must close. I haven’t heard the first word from Julia though I sent a letter to Mt. Vernon to anticipate her arrival. Neither have I heard from Charles or Abbie or anyone except Mary.

In haste. Your affectionate son, — T. F. Vaill


Theodore wrote this marvelous letter to his father from a camp near Front Royal, Virginia. We learn from a subsequent letter that Theodore had been in a hospital at Georgetown, Maryland, until October 2, 1864 when he left to rejoin his regiment in Virginia. He found them at Fisher’s Hill on the 9th of October where they had just tasted victory. Theodore describes his journey in some detail — most of it as part of a well-guarded caravan of supply wagons that made their way down the Shenandoah Valley through Martinsburg and Winchester and Strasburg.


Headquarters 2nd Connecticut Volunteer Artillery
Camp 3 miles west of Front Royal, Va.
Monday afternoon, October 10, 1864

Dear Father,

I received your letter of September 30th last Saturday. It was in the supply train that I came with from Martinsburg, but of course I could not get it until it & I reached the regiment. But to go back a little (for which extraordinary proceeding I have very worthy precedents) — I left Washington at 8:30 P.M. Sunday eve, Oct. 2, reached Harper’s Ferry at 1 A.M. next morning. Monday A.M., went to Sandy Hook Hospital & visited Ward Master [E. Goodwin] Osborne ¹ who has ingratiated himself into the favor of the Surgeon & who is getting to be quite a Surgeon himself, being trusted with the dressing & care of severe wounds. (And here I must digress to relate Goodwin’s statement of the political feeling in his wards. He says he took a vote among the patients, which stood thus — Lincoln 16, McClellan 2. He then gave each of the two copperheads an injection, took another vote, & found his ward unanimous for Lincoln.)

Monday, P. M., Oct. 3, I went on to Martinsburg which is now the base, being nearer to Winchester by 8 miles than Harper’s Ferry is. It is a village about as large as Litchfield [Ct.]  — yes larger — but a very inferior, plebian place, there being not one fine house or opulent seat in or around it. But the re-opening of the Baltimore & Ohio Railroad, the immense travel, & the military operations, make it just now a perfect Babylon.

Ruins of the Depot at Martinsburg, Virginia (1864)

No one can travel in the Valley now without strong military protection on account of guerrillas & I had to wait there until Wednesday P. M., Oct. 5, in order to go with the “train” which consisted of 400 wagons, each covered with canvas & drawn by six mules with a driver on the near-wheel-mule & loaded (the wagon, not the mule) with hard bread, pork, coffee, sugar, shoes, trousers, blankets, cartridges, shot shell & mail bags & medicines. Two or three regiments of infantry & strong detachments of cavalry accompany the trains — part well in front as advance guard, part as near guard, & flankers in the woods & along the country on either side — and a force marches at intervals of fifty wagons or so. Where the road, country & streams admit of it, they double the wagons, which reduces the length of the train one half. But this is impracticable in some cases & the train stretches miles away. A halt of one wagon on account of accident or anything else, halts the train, so it can be imagined that supplying an army containing as many mouths as Hartford City by hauling supplies 70 miles through a hostile country is not so simple an undertaking as the Home Guards imagine. On the way from Martinsville to Winchester, a cavalryman was shot from the woods & buried by the roadside.

We reached Winchester on Thursday. It is a fine old town, as large as New London, with many lordly mansions in the suburbs, among them that of Mason of the well known firm of Mason & Slidell. It is now full of wounded of both armies. On Friday, the train moved on & on approaching Strasburg, we found that Sheridan was there with his whole army, just arrived from Harrisonburg. I reached the regiment encamped just north of Fisher’s Hill on Saturday evening & found the boys all well. All there are there of the Happy Family are Dwight Stone, Lewis Bissell, & Myron [E.] Kilbourn. I was much surprised to find Myron there. He is very well, however, & looks as natural as he did before Cold Harbor — minus two fingers.

The soldiers have had a taste of victory & have seen thousands of rebels flying pell mell before them & I have never seen a more hilarious set of beings in my life. A cheer will begin in some camp & catch from brigade to brigade until the Blue Ridge flings the shout over to the Alleghanies & the Valley, far up & down, reverberates with the songs & shouts of triumph! The army is all right. They believe that rebels who showed the soles of their shoes as they did at Winchester — & particularly at Fisher’s Hill — will soon see the propriety of yielding to the government which, as Gen. Sherman told Hood, all must respect & obey.²

Brig. Gen. Tolbert (1864)

This morning we moved to this place & it looks as though we were going to pass through Manassas Gap & move toward Washington. We are now encamped for the night. Sheridan is in the habit of sending news of successful operations immediately around to all the troops of his command for the purpose of encouraging them. (This is a new thing. Heretofore, we have had to depend on rumor, personal knowledge, or the newspaper.) Last night an official dispatch was sent from Sheridan’s Headquarters stating that the rebels (who have been harassing our rear from Harrisonburg to this place) had been shipped by [Alfred Thomas] Torbert’s Cavalry & that we had taken (11) eleven pieces of artillery, 30 wagons, 300 prisoners, & driven the rebels back 20 miles. This was Saturday night & Sunday. It is unofficially reported that Sheridan left a train of empty wagons behind as bait to be pursued & they bit & were bitten! I don’t know where we shall go from here but I have reason to believe that we are going straight to Washington or Alexandria, en route to City Point. Troops are to be at work all night tonight building two bridges near here & that makes me think so.³

Col. Rand MacKenzie

Col. [Ranald Slidell] MacKenzie’s bravery is on the lips of every man in the regiment. Officers & men, friend, & those not friendly, all say that during the late battle [Third Battle of Wincheser, or Battle of Opequon], he seemed to care no more for shot & shell than a bull would care for snow flakes on his nose. Col. Hubbard told me that he (McKenzie) handled the regiment with the same & greater coolness than he would on drill. Col. M’s horse was cut almost in two by a shell & of course the Col. came down. “Well,” said he, by way of a joke, “this is dismounting without numbers.” I had suspected ever since I knew him that he was made of the right kind of fighting material.

I am now the only staff officer present. [Chester D.] Cleveland (Ordnance Officer) is acting Brigade Ord. Officer, Maj. Skinner is in Winsted wounded. Maj. [James Q.] Rice killed. Col. [James] Hubbard absent sick, & Q.M. [Edward C.] Huxley back at Winchester. Chaplain ditto. Capt. [E. W.]  Jones [of Co. F] is acting Major. I have plenty of work, I tell you, & [Morris H.] Sanford is tickled beyond all measure to have me back. He says the hoss was a very convenient thing, but he would rather foot it & be in the line fifty times over than ride & be Col. MacKenzie’s adjutant. He (Sanford) is now in command of “H” Company, late Capt. [Frederick M.] Berry’s.

Capt. Frederick M. Berry died of wounds received at Winchester in September 1864

I send you a map which you can mark on with ink or pencil if you wish to trace any new route. I have marked it somewhat myself. I received with your letter one from [sister] Mary, one from Mr. Richards, & one from Capt. Mason & shall remember them all as soon as possible.

Please write soon & C. B. V. please send me another handkerchief & another napkin. With much love, — Theodore

P. S. The map I enclose is a poor concern, & is only meant for a marking map. I have indicated our present position thus, “Camp, Oct. 10.” The rebels at last account were at New Market. They cannot attack us in any respectable force without giving up Richmond to the tender mercies of Grant. Hard frost here last night & the men’s bones ached. They swarmed around fires very early this morning. Weather now very pleasant.


¹ E. Goodwin Osborne enlisted as a private in the 2nd Connecticut Heavy Artillery but rose tho the rank of sergeant major. We learn from this letter that he was serving as a ward master at the Sandy Hook Hospital in Maryland (near Harpers Ferry) in October 1864. Osborne was later killed at Fort Fisher in 1865. Homer Curtis, a comrade in the 2nd Connecticut Heavy Artillery,  said of him, “a finer man never was called up to die for his friends by the hand of his & their foes.”  Three weeks before his death, Osborne was detailed a musician but “Osborne was unwilling to blow a horn while his comrades carried muskets” and so he returned to the company just in time to participate in the fateful charge at Fort Fisher. 

² Gen. William T. Sherman’s letter to James M. Calhoun, mayor of Atlanta, dated 12 September 1864.

³ This is a reference to the Battle of Tom’s Brook fought on 9 October 1864 in which Brig. Gen. Alfred Torbert routed Rosser’s Laurel Brigade so quickly that Union soldiers called it the “Woodstock Races.”


In this letter to his sister, Mary Woolsey Vaill (1842-1871) , Theodore briefly reprises the tale of his journey from a hospital in Georgetown, Maryland, to join his regiment near Front Royal, Virginia, in early October 1864. He speculates on the various routes the regiment may take in the days and weeks ahead as part of Sheridan’s Army adding that Sheridan “don’t tell anybody what he is going to do.”


Addressed to Miss Mary W. Vaill, Rye, New York

Headquarters 2nd C. V. A. [Connecticut Volunteer Artillery] near Front Royal, Va.
Tuesday, October 11, 1864

My dear sister Mary,

Yours of September 29th was duly received. I left the hospital at Georgetown October 2nd & reached the regiment on the 9th near Fisher’s Hill — the place where they whipped the rebels & sent them flying like sheep. We are now encamped 3 miles from (west of) Front Royal, but where we shall go from here, or when, I don’t know. There is one peculiarity about Sheridan — he don’t tell anybody what he is going to do. It is doubtful whether even the Corps commanders know until almost the time arrives whether we are to go north, south, east or west. But of course, everybody keeps up a great thinking & there are all sorts of speculations. We may remain here or hereabouts until Lincoln is re-elected, in view of the fact that the rebels will surely do something perfectly desperate in order to assist McClellan. It is even possible that they may load their whole army with eight or ten days rations, leave Richmond to its fate, & march with superhuman speed on Washington.

2nd, we may return to Harper’s Ferry & go to Petersburg to reinforce Grant. If this course is pursued, it will be on the presumption that the rebels will not attempt another northern invasion (& indeed there is no rebel force whom opposed can cause the least anxiety to Sheridan’s Army unless it comes from Richmond & Petersburg & Grant would know if any large force were withdrawn from his front in less than five hours).

3rd, we may march from here directly east to Washington or Alexandria & go from there to City Point.

4th, we may go east from here & stay on the east side of the Blue Ridge at Manassas or thereabout until after election. You can’t think how much the army looks upon the election as decisive of the war. In some regiments there is not a single man who will vote for McClellan. Some regiments have two or three McClellanites but I know that fully 9/10 of the army vote will be for Lincoln. Lest I should get the figure too high, I will say 4/5 — but we shall see. If the rebel army were to vote, ever real rebel among them would vote for G. B. McClellan.

Col. MacKenzie — “behaved with the utmost bravery…but the officers & men don’t love him at all.”

I have talked with several of the women in the Valley as I passed their houses and their most anxious question was whether Lincoln or McClellan was probably going to be President. But I am very busy & can’t write more. What you say about a certain young lady may be very true but I have forgotten how she looks. Can’t you smuggle her picture into a letter & send it to me? I saw many very beautiful women in Winchester but they are very rebellious. Col. MacKenzie behaved with the utmost bravery in the late battles but the officers & men don’t love him at all. All the officers & men in the 2nd C. V. A. behaved well. Please write soon again.

With much love, — Theodore

I send you a true McClellan paper. Send it home when you have read it. Tell Charles to get you the “Times” review of McClellan by William Swinton published in pamphlet form.


Theodore wrote this letter to his sister, Mary Woolsey Vaill (1842-1871), from the headquarters of the 2nd Connecticut Volunteer Artillery (C. V. A.) from some unidentified location in North Carolina in the days leading up to the assault on Fort Fisher. He mentions the promotions of their mutual Litchfield friends, Good[win] Osborne to Sergeant Major and Dwight Stone to 2nd Lieutenant.


Addressed to Miss Mary W. Vaill, Rye, West Chester Co,, New York

Headquarters 2nd C. V. A.
March 12, 1865

Dear Sister Mary,

Your good letter of the 8th inst. was received last night and although I have no news to send, I will write a word so that you will owe me another letter. I received a letter from Charles lately inclosing a poem from Lizzie which merits a reply in kind. But there is no place to make poetry & I can’t do it. I send, however, an epic which I picked up down yonder and which is what I doubtless would write if I had time. Send it to father.

I see by the Litchfield Enquirer that I have been made into a captain — but I shall decline. I received your letter from Mrs. Hoyt containing Cornelius’ letter & I regret to say that I lost them & the most careful hunting don’t show their whereabouts. Things that get lost down here are never found. I will write to Mrs. Hoyt when I get time & tell her about it.

It is strange that I don’t hear again from [brother] Joe. The only letter I have received from him was the one I sent home. Expect George M. Woodruff down here every day to take the votes for the coming election. Good[win] Osborne is Sergeant Major & Dwight Stone 2nd Lieutenant.

Very fine weather today. We are waiting with anxiety & confidence for good news from Sherman and it may be that the whole thing will be settled by a crushing defeat of the rebels in North Carolina. At any rate, everybody thinks that it will very soon be done.

Please write soon. With much love, — Theodore

In a hurry.

aacivvail7 - Version 2
Poetry enclosed in Vaill’s Letter


Theodore wrote this letter to his sister, Julia Maria Vaill (1839-1912), from Fort Ethan Allen near the end of his service in the 2nd Connecticut Volunteer Artillery (C.V.A.), formerly the 19th Connecticut Volunteers.


Addressed to Miss Julia M. Vaill, Litchfield, Connecticut

Headquarters 2nd Brigde
DeRussy’s Div. 22nd Army Corps
Fort Ethan Allen, Virginia
July 31, 1865

Dear Sister Lizzie,

Your tripartite letter of the 17th inst. was duly received day before yesterday. Where it had been for 12 days, I couldn’t say. Owe you a poetry letter but can’t pay that in kind until I have more time & more inspiration. See by your letter that you won;t be at home to read this, so I will shorten up on you.

Dear Sister Classy,

You remind me that Charley wrote me a long letter when I was in Brooklyn & want to know why I didn’t answer it. Well, it was because I had no eyes to write about those times — leastways to write more than I was “kimpulsioned.”  You disremember to specify in your letter what time you are going to leave Litchfield & return to that place on One Idea. So I can’t tell whether I shall get home to see you or not. But if I don’t, I propose to go to see One Ida, either at Stamford or out your way.

No more time this morning because I am busy just now with monthly returns for July. Please write & tell me when Charley is coming. In haste.

Dear Sister Julia,

I hope you won’t fail to fulfill your promise to “endeavor to have some of the prettiest damsels answer my Library letter.” I have seen nothing of [brother] Joe yet. I have reconsidered my purpose of tendering my resignation immediately & shall wait a little — because if I tender my resignation, I cannot get the extra 3 month’s pay — and it is very probable that we shall be mustered out within a few weeks. But if you are going to be at home long enough, I think I shall apply for a Leave of Absence & visit you.

Now please reply at once & send me a complete “Roster” of the household & let me know how long each one stays. My horse’s left eye is something the matter with it & I am afraid she is going to lose it.

In haste, with much love to all, — Theodore


Theodore wrote this letter to his brother, Charles Benjamin Vaill (1826-1881), just before the 2nd Connecticut Volunteer Artillery was mustered out of the service. Theodore describes the mountain of paperwork he must complete before the men can muster out.


Addressed to Mrs. Charles B. Vaill, Litchfield, Conn.

Headquarters 2nd C. V. A.
Fort Ethan Allen, Virginia
Thursday Eve., August 10, 1865

Dear Brother Charles,

An order was received tonight to the effect that the 2nd C. V. A. would be mustered out immediately. So you may expect to see us in a few days. [Brother] Joe left this morning for Baltimore. I went down with him to the Depot. Please send this to Litchfield. In haste.

Your brother, — T. F. Vaill

P.S. To Father. If Mr. Dudley still wants me to bring a boy, let me know. I presume we shall be in New Haven by the 20th of this month.

Headquarters 2nd C. V. A.
Fort Ethan Allen, Va.
August 15th, 1865

Dear Brother Charles,

We are to be mustered out on Friday, August 18, & shall probably leave for New Haven on Saturday or Sunday. We have to make out seven muster out rolls, each containing the name, description, enlistment, muster, pay acct., clothing acct., bounty acct., & complete history of each & every officer & man that now belongs — or ever did belong — to the regiment, & as the Old 19th too away nearly every man that didn’t execute his sign manual with a X, you may be sure that every officer down here is busy. Besides, the books & records of every company are to be completely posted, packed & labelled.

Why don’t I get any letters? There’s time enough before we get away from here. Please send this to Litchfield.

In haste, — Theodore



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