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Of all the towns and villages in the Union or Confederacy during the Civil War, Winchester, Virginia, was fought over most. The sleepy town of just 4,400 residents changed hands 72 times, including 13 times in one  day. This information comes from the careful record of Julia Chase, a 30-year-old Winchester resident who faithfully recorded not just the movement of armies but also mundane details of life in the town. Living just three blocks south of Chase, diarist Kate Sperry viewed the war from an entirely different perspective.

Unlike the majority of Winchester’s citizens, Chase was a committed Unionist. Although Unionist sentiment was not common in the Shenandoah Valley community, it did have a small but passionate presence. Winchester resident Robert Conrad led the fight to keep Virginia in the Union during the state’s secession convention, and only joined the Confederate cause after the firing on Fort Sumter in April 1861. Rebecca Wright, who lived directly across the street from Chase at the intersection of Fairfax and Loudoun streets, was the spy who told Maj. Gen. Philip Sheridan of the departure of a Confederate division from the town in mid-September 1864, bringing on the Third Battle of Winchester and the final occupation of the town by the Federals.

Chase’s diary begins on July 2, 1861, and concludes on September 20, 1864, the day after the Third Battle of Winchester. She closely chronicled the day-to-day affairs of the armies as they passed through the town. Her Unionist sympathies and her religious beliefs are conspicuous throughout her diary.

Born in Maine in 1831, Chase lived with her parents during the war. Like her Confederate counterparts, her family suffered when the town was occupied by the opposing side. They also had to cope with the trauma of having many close friends and neighbors consider them the enemy after the war began. Their home was occasionally searched, and the family fell victim to the usual indignities that beleaguered a Unionist family living within the Confederacy. Her sick father, who served as postmaster, was taken prisoner in 1862 by Maj. Gen. Thomas J. “Stonewall” Jackson and held for 12 days. That experience exacerbated his health problems, and he eventually died in 1864.

Her account of the approach of the Confederates in June 1863, the Second Battle of Winchester (June 14-15) and the invasion of Pennsylvania by the Army of Northern Virginia is filled with helpless indignation at the apparent inability of the North to defend itself. This isn’t surprising, as this period was a time of great joy for the Southern sympathizers in Winchester, and wild rumors were flying through the streets every day, mostly presuming success for Confederate forces everywhere. This sent Chase into a deep depression, and her appeals for divine help are at times heart-wrenching. Her grim diary entry on July 5, 1863, is particularly ironic, because it coincides with the evacuation of the Army of Northern Virginia after its defeat at Gettysburg and was made the day after Maj. Gen. Ulysses S. Grant accepted the surrender of Vicksburg—events she obviously was not yet aware of.

Fellow diarist Kate Sperry was born in Winchester in 1843. She was an an ardent Southern sympathizer and was overjoyed at the outcome of events of June 1863. Sperry was 18 years old when the war began, and lived downtown at 41 South Loudoun St. with her grandfather, Peter Sperry, and her two sisters. The title of her diary, “Surrender? Never Surrender!” makes it perfectly clear that the teenager was as passionate for the cause of Southern independence as Chase was opposed to it. It also reveals an intelligent, daring young lady who wasn’t afraid to express her opinions on a variety of subjects. Her diary is sprinkled with comments on the famous and the infamous, as well as on her friends and relatives.

Sperry’s diary begins on July 13, 1861, and is filled with plenty of romance, since the attractive teenager spent a great deal of her time flirting with Confederate soldiers in the town and surrounding area. Despite the constant parade of gentlemen callers, Kate’s heart was set on just one soldier, Dr. Enoch Hunt of the 2nd Mississippi Infantry. With the death of her grandfather in August 1864, Sperry was forced to make a momentous decision. A month later, she moved to North Carolina, where she married Hunt on December 2, 1864. They moved to Mississippi after the war, where she died in 1886 at the age of 43. Her diary entries leading up to the Second Battle of Winchester are especially interesting since Sperry was living with her cousin Harriet Chrisman between Middletown and Stephens City (Newtown). She moved home only after the Confederates occupied Winchester following the battle. The Chrisman home was directly between the lines of the Union force under Maj. Gen. Robert Milroy occupying Winchester and the Confederate cavalry brigade of Brig. Gen. Albert Jenkins in the valley. While at the Chrisman home, Kate and Harriet visited the Confederate pickets near Fisher’s Hill on a regular basis and also aggressively confronted any Union force sent up the Valley Pike to scout the Confederate position. Just prior to the Second Battle of Winchester, Sperry and her friends witnessed an ambush of 63 members of Jenkins’ cavalry directly in front of the Chrisman home. Sperry described the battle, the participants and its aftermath in great detail, as well as the occupation of Winchester and the parade of Union prisoners following the battle.

Sperry, Tuesday, June 9, 1863

Got up early this morning—Kate [an acquaintance] and I started before sunrise and soon after reaching her house we were en route for Fishers Hill—didn’t meet a soldier until we got beyond Strasburg near the Stone Bridge where [we met] two of our officers, Major Harding and Capt. Griffin….They tried their best to get us through to Woodstock but the army was under marching orders and pickets positively forbidden to let anyone through….Kate had a cake for Gen. Jenkins, but gave it to Maj. Harding—the latter declares we have 20,000 men within 20 miles ready at a moment to sweep down on old Milroy and that it won’t be a week before we have the town [Winchester]….

Chase, Wednesday, June 10, 1863

A cavalry fight took place yesterday between the Federal Cavalry and that under Rebel Genl. Stuart on the Rappahannock. Stuart has been massing a large force of cavalry at Beverley’s Fords, as is supposed with the intention of [making] a raid. They attempted to cross, but were repulsed by our troops driving them back after an obstinate fight, holding the south bank of the river.

Chase, Thursday, June 11, 1863

Today’s paper says that the cavalry forces of the Army of the Potomac, gained a glorious victory over Genl. Stuart and discovered his arrangement for a raid into Maryland and Pennsylvania. 200 prisoners were taken and a large number of the enemy killed and wounded. It was reported a day or two since that the Rebels were in force in the Valley of Shenandoah but none have been found between here and Strasburg.

Sperry, Friday, June 12, 1863

About four o’clock out came some Yankees and in a few moments about 220 cavalry passed up the road. We stood at the gate in excellent spirits, were sure they’d be whipped. Major Kervin, a very fine looking Yank, and I had a big quarrel—he tried to be sarcastic—said he supposed the appearance of that company of Rebels had cheered me and asked Harriet how many there were—she told him there were six or eight, she didn’t remember for she couldn’t count—he stared at her (several other officers and a rascally “Jesse Scout” were by) to see if she were joking…—in a few moments 411 infantry and two cannon came up—the infantry were placed in a strip of woods about a hundred yards from the house and a stone’s throw from the road on the right-hand side of the road towards Middletown—they were then divided into three squads—one stayed in the woods—one laid down behind a tall rail fence this side of the woods—said fence forming a right angle with woods and road—on the left of the road right before the house which is on the right, the two cannon were placed and the third squad was held in reserve behind a small hill in the same field, which has very tall orchard grass growing in it—the horses were unlimbered from the cannon and taken behind this hill and only two men left to fire the cannon at the right time, the fence pulled down only sufficiently to get in good range of the road, and all was quiet. Whilst these arrangements were being made, the 220 cavalry advanced as far as Middletown, our pickets withdrawing before them, then all of a sudden Captain Rasin of Co. E, First Maryland Cavalry with 63 men charged them—killed one and wounded several—then the Yanks ran and our noble 63 after them—we went to the garret window and could see the Yanks running and our men after them—still we feared nothing until they came in sight and the Yankee cavalry had got below the house—I thought my heart would burst—poor souls—coming on to certain death, for the clouds of dust made by the Yanks in running prevented the infantry being seen by our soldiers ’til too late— brave souls, they came tearing on, cheering with all their might. When one half got past, the infantry fired—my heart was almost broken. One half fell off their horses in the road and the rest retreated whilst the tow cannon loaded with grape was poured into them—three were instantly killed and one whose horse was shot fell almost before the door, the horse on him—he was finally brought in—never spoke, but died in ten minutes—his name was Sergt. Gimmel—Eastern Shore, Maryland. During all this time a Yankee surgeon was cursing us to everything…— all because we were sympathising with our dying soldier—we wanted to tell them that our men would soon be down, but we knew they suspected nothing and didn’t want to let them have an inkling of what was going on. When our men made the charge we were all at the end of the window near the top of the house—we screamed, begged, and waved them back, but it was too late—about eight or ten of our men were wounded, the same taken prisoners—probably a few more, and four killed. One of the dead was Mr. Fitz Patrick, who belonged to Major Gilmore’s company—he led the charge with drawn saber—he never carries a pistol. Major Kervin, the villain, came in the yard and ran right up to me, stuck his nose almost in my face—I returned the look and never moved—suppose he wanted to know me the next time he comes out, which I hope will be when he’s a prisoner. The Yankees told us to come to the ambulance and see if any of the wounded were our friends. I went out with the rest and Kervin spurred his horse so as to make it kick me—I know he did it on purpose—he nearly rode over me—so I blazed away at him and ordered him out of my way, but he wouldn’t move—gave me a look which he thought would annihilate me and said I was not a lady….The ambulance had just started when four of our men came with a flag of truce to find out something about the wounded, but Kervin wouldn’t have anything to do with it, wouldn’t pay any attention to it but went off to Winchester. When the four came down one proved to be Mr. Wagner, who formerly belonged to the First Maryland Infantry—now in the cavalry. Mr. Rogers, the soldier who came down with me today, was taken prisoner, but we didn’t see him—perhaps he was wounded—I expect he was. We had all four of the dead brought in the yard and washed their faces—every one was good-looking—Mr. Fitz Patrick was shot in the face—the ball went in near his left ear and came out his right eye—Mr. Gimmel was shot in his stomach—and I forgot where Mr. Howard received his death wound—he was only 19 years old and so handsome— the Yankees didn’t get his body, for his pockets were full and the rest were rifled—I have his purse—it has considerable specie in it—will give it to Major Gilmore tomorrow—the other man killed was named Richard West. All belonged, with the exception of Mr. Fitz Patrick, to Co. E, First Maryland Cavalry. It was an unfortunate occurrence. Captain Rasin had orders not to fight but try to bring the Yanks up above Middletown, but he thought it was only cavalry and he could whip them—oh, it was dreadful to bear the taunts, insults, and curses of the Yankees over our dead men—nearly every girl from Newtown came out to see the dead and all the children from town also—they cried over them as though their hearts would break it was too sad.— I feel such oppression I can write nothing more about it. The enemy didn’t get a single horse from our men—they killed five or six, but the rest ran back up the road.

Chase, Saturday, June 13, 1863

What exciting times we are passing through since Friday. Skirmishing commenced on that day between the Confederate cavalry and Federals. Quite a number of prisoners were taken, several being wounded. They were brought to the hospital, there wounds dressed and proper care given them. Yesterday, fighting continued all day and cannonading was going on through all its hours. The Rebels are coming we hear in great force, Ewell it is said being here. The town is all in an uproar, wagons lining the streets all the day, cavalry and infantry passing by, the Secessionists were very joyful flocking to the sutlers, buying up all they can for their friends, while the Unionists are in an anxious state of mind. Reinforcements are looked for tonight, but not to the number requisite. God in his mercy, grant that Winchester may not be given up to the Rebels, we dread their appearance….Later—It is said that our soldiers are fighting bravely this morning, capturing a battery and quite a number of prisoners, but as it is said Genl. Milroy—was the attacking party, we are little superstitious that he will be defeated. Our prayer will go up for the help of the Almighty, that he will not turn a deaf ear to our entreaties. 12 o’clock—Cannonading since early this morning, still going on. It is said that Genl. Lee’s whole force is in the Valley, Genl. Hooker in his rear, how true it is we can’t say, this week will decide very important events, either for or against our country’s cause. The armies are drawn up in line of battle just at the edge of town.

Sperry, Saturday, June 13, 1863

Today has been almost happy to me— about daylight our soldiers came down— Maj. Gilmore with them—he almost distressed to death over Mr. Fitz P.—I gave him the purse and he says he’ll send it to the mother of the young man. On yesterday Gen. Jenkins went to Front Royal to join Gen. Ewell, who is there—nothing is here now but the Maryland Line—they all passed by—Gens. Smith, Gordon, and Early met them in Newtown from Front Royal—a portion of Gen. Ewell’s div.— and they’re now before Winchester— Imboden is on the Romney road, Ewell on Front Royal Road, and some one else— Gen. Rodes, I think—on Martinsburg Pike—so Mr. Milroy is completely surrounded—the best of it is that he never knew a word of it ’til the middle of today and our army was right there….The four dead soldiers were buried this evening— cannon has been booming all afternoon and late tonight—the Yanks were coming out to hunt up the company they whipped yesterday—got nearly to Kernstown and the Md. Line gave them fits—drove them into Winchester—I hope we’ll get possession tomorrow.

Chase, Sunday, June 14, 1863

The Rebels took possession of our town at 5 o’clock this morning and we are now in Dixie. Oh what a sad, sad day this has been for us. Genl. Milroy left the fort during the night but with the loss of 3,800 taken prisoners, and 300 wagons heavily loaded, besides a great many horses. This is considered a glorious victory by the Rebels….We hear that Genl. Milroy had orders on Friday to fall back to Harpers Ferry but was determined to give fight first. Had he removed his army train, it would not have been so bad, but to have so much captured, it is outrageous.

Sperry, Sunday afternoon, June 14, 1863

Have heard cannon all day—Milroy is not ready to surrender yet—all the Yanks in fortifications—two ladies came out last night—said they had no difficulty at all— didn’t see the Yanks—15 wounded Yanks at Kernstown, some with arms and legs amputated—a good many Yanks killed— as I write I hear cannon roaring—Oh Lord, protect us and our Army!

Sperry, Sunday night (10 p.m.), June 14, 1863

…firing ceased late this evening and it’s supposed our men will enter Winchester tomorrow…about 600 wagons encamped here this evening—will stay all night and start for Winchester as soon as the town is in our possession. Never heard such terrific cannonading in all my life—am afraid our town will yet be blown to atoms.

Sperry, Monday, June 15, 1863

Am safely home and all well except Aunt W.—three shells went through Capt. Cootz’s house. Came in this morning with Harriet Chrisman, had to pass the whole baggage train. The Yanks evacuated the “Fort” as quietly as possible about three o’clock this morning and we captured, killed and wounded at least 7,000, and old Milroy hadn’t many more—he managed to take his escape, but we got all his stores—it’s been a joyful day for us….

Chase, Tuesday, June 16, 1863

We hear that Genl. Lee has possession of Arlington Heights and Longstreet has entered Hagerstown, without the least obstruction, but we don’t believe a word of it. In all probability Stuart has made a raid into Pennsylvania, and that there will be a desperate struggle on the part of the Southern army, there is not the least doubt; they have taken the aggressive, and we expect to hear of Washington being taken, also that they will invade the Northern States; if this will not open the eyes of the whole nation and call forth all their energies nothing will. It was the saddest site [sic] to see so many prisoners taken, and great number of officers. Oh how mortifying and provoking, we had expected different things from Genl. Milroy.

Sperry, Friday, June 19, 1863

A large portion of Yankee prisoners were sent off yesterday and more left today— the wretches—they swear it’s not the last time they’ll be here and as usual make great threats—one them wondered what on earth Jeff. Davis would do with so many Yanks in Richmond….Our army is advancing towards Md. The Yanks are scared to death in Washington—old Hooker is near there….

Chase, Saturday, June 20, 1863

Is there to be no end to the prisoners and stores that are captured by the Rebels? Is the whole Federal army asleep or lain down their arms? Some 49 wagons are passing by with captured stores from Maryland. Seem to us that the Federalists are just giving everything over into the hands of the Rebels. When will they arouse from their stupor? Are there no brave soldiers in our army? Are our generals so stupid that they permit these things? God Almighty, stir them up…and help them to make a bold strike into the Rebellion. It is said that Cumberland, Williamsport, Hagerstown, Greencastle, and Carlisle are in possession of the Rebels, passing along unmolested, without the least opposition. The court house yard was filled yesterday with prisoners, taken some at Aldie, others a few miles beyond Martinsburg. All have been sent to Richmond today. We fear that too many were anxious to be prisoners. Unless our soldiers and officers enter in the war with heart and soul, determined to do their duty to their country, and as soldiers, they will never gain a victory. This is too much drinking and money making to accomplish much, and how can we expect victories while such things continue.

Sperry, Tuesday, June 23, 1863

Gen. Jenkins is “playing hob” with Union folks in Penn. Got a many horses and cattle—it’s reported there’s been a riot in Balt. but I don’t believe it—it’s stated that the Southerners [citizens] hold the place.

Chase, Tuesday, June 23, 1863

The Rebels under Genl. Ewell are in Pennsylvania, and are accomplishing their object in capturing horses, Negroes, and cattle. We had supposed that something would have been done their on the part of the Unionists, but so far as we can learn the Rebels have marched through without the least resistance. Great God! How long shall this state of affairs continue? Hast thou given up the people of the North to their own destruction, Is there no hope for our country?

Chase, Sunday, July 5, 1863

Genl. Hooker has been superseded by Genl. Meade. A battle took place between him and Genl. Lee near Gettysburg on Friday, Genl. Lee having gained the victory, Meade falling back towards Baltimore, and is hard pressed by Lee, probably fighting may be going on today, unless the whole Federal army has been cut to pieces. Our hope is all gone and we cannot expect but that a few days will determine the fate of Baltimore and Washington, that our government is not able to maintain itself. Oh God! Thou knowest what is best for us, help us to submit to thy decrees, feeling that thou art just, that our wickedness is so great, that our country’s cause cannot be a just and righteous one and that thou art arrayed against us. If thou be not for us, who shall stand? Have mercy, we beseech thee, upon us. Genl. Grant it is said has also been defeated at Vicksburg. If our armies cannot succeed better, it would be far preferable that peace should follow than to sacrifice so many lives, and be considered a disgrace forever. How can we expect much from our soldiers when we hear the Pennsylvanians, instead of making a bold resistance to the invaders who are now in their state, instead of boldly defending their homes and firesides, should ingloriously run away into other states. Can it be possible that we are a nation of cowards?


Originally published in the June 2006 issue of Civil War Times. To subscribe, click here