May 25, 1862 - First Winchester

May 25, 1862

First Winchester

Winchester, VA (Frederick County)

US- Banks: Colonel George Gordon’s 3rd Brigade

vs

CSA- Jackson: General Dick Taylor’s Louisiana Brigade, reinforced by the 10th and 23rd Virginia

* Following Banks' victory over Jackson at Kernstown...

* Confederate victory, though they lost 16,000 to the Union's 6,500, part of Jackson's Shenandoah Valley Campaign, following his victories at McDowell and Front Royal 

* Banks retreats to Williamsport, MD

Opps. Guess I'll be back for 2nd Winchester....

...which I visited in the summer of 2025.

https://www.hmdb.org/m.asp?m=241604

Photographed by Craig Swain, August 25, 2007

May 25, 1862

General Stonewall Jackson with 16,000 Confederates defeated General N.P. Banks and 6,000 Federals. On May 24, at Middletown, 12 miles South, Jackson attacked Banks’ army withdrawing toward Winchester, cutting off the rear guard and capturing or destroying a large number of wagons. Jackson launched his attack on Winchester at 5 a.m. May 25. Contesting this thrust was Colonel George Gordon’s 3rd Brigade. General Dick Taylor’s Louisiana Brigade, reinforced by the 10th and 23rd Virginia, succeeded in flanking Gordon on the west, while troops of Jackson’s division pressed Gordon’s center and left. General R.S. Ewell on the southeast approaches to Winchester saw his first attack repulsed. Calling up his reserves, Ewell moved against Colonel D. Donnelly’s Union Brigade. All Federal positions were taken by 8 a.m. and Banks’ army fled North through town. Confederate pursuit was hindered by lack of Cavalry.

*

https://www.hmdb.org/m.asp?m=241384

May 25, 1862 between Confederates under Brig. Gen. T.J. “Stonewall” Jackson and the Federals under Maj. Gen. N.P. Banks began just south of this site. The Federals were driven in retreat through Winchester’s streets with loss of stores and many prisoners.

Confederates engaged, 16,000, casualties 400. Federals engaged, 8,000, casualties 2017.

*

https://www.hmdb.org/m.asp?m=2616

Abram’s Delight is the oldest home in Winchester. 582 acres of land was granted to Abraham Hollingsworth in 1734. The first log house on the site was replaced by the present stone structure built in 1754 by Isaac Hollingsworth, a Quaker, son of Abraham. Family heirlooms and original objects from the mid 18th and early 19th century furnish the home of one of Winchester's most prominent families.

https://www.hmdb.org/m.asp?m=254266

Abram's Delight

“Best wishes to all at your house”

The oldest dwelling in Winchester, Abram’s Delight experienced the passage of both Union and Confederate armies during the war. Although the property stood in the path of the First Battle of Winchester on May 25, 1862, it survived and now illustrates the civilian side of the conflict.

Mary Hollingsworth and her siblings, Jonah and Annie, occupied the house during the war. Standing more than six feet tall, Mary Hollingsworth may have impersonated a man to spy for the Confederates, according to local tradition. She also gave meals and shelter to Union soldiers on several occasions. Early in the war, a soldier wrote, “My best wishes to all at your house, and all those who were there during my stay with you.” William Darnel, of the 3rd West Virginia Cavalry, thanked her for her hospitality in the spring of 1865: “I embrace this mode of bidding you adieu and also to express my thanks for the kindness manifested during my sojourn at your place.”

In the spring of 1864, Union Gen. Franz Sigel and several of his staff members occupied Abram’s Delight. Sigel paid Hollingsworth $5 for her troubles. After the war, she filed a  claim with the Southern Claims Commission for damage done to her property. The commission denied her request, however, stating that the damage occurred as result of the “fortunes of war.”

https://www.hmdb.org/m.asp?m=19508

The Hollingsworth Family Settlement

Shenandoah University's History and Tourism Center sits on land once owned by the Hollingsworth family. The Hollingsworth home, "Abram's Delight," is now a nearby museum.

One of the first settlers to come to the Shenandoah Valley, Abraham Hollingsworth settled on 582 acres of land that had a large spring. Tradition states that Abraham paid for the property three times: "First, a cow, a calf and a piece of red cloth to the Shawnee Indians; next, a sum of money to the King's agent; and finally, a sum of money to Lord Fairfax."

After Abraham's death, his son, Isaac became the owner of the property. "Abram's Delight," the oldest existing house in Winchester, was built in 1754 by Isaac near the spring that his father had declared a "delight to behold." The nearby stone mill building was built in 1833 by David Hollingsworth, the great-grandson of the original settler, Abraham. It was built on the site of an earlier grist mill operated by family members since the mid-18th century.

The body of water before you is produced by a spring that attracted the first Hollingsworth to choose the property to be his family's home. Built before 1753, this important resource was used to turn the wheels of the first mill, as recorded in the diaries of the Morovian Single Brethren, who stopped at the Hollingsworth mill to purchase feed for their horses in October 1753.

The pond also provided many recreational opportunities for the citizens of Winchester. During the late 19th century, people often used the small island on the pond for picnics, arriving by small boats. An article in the Winchester Star in June 1907, said: "One of the most delightful moonlight picnics given at Rouss Spring...took place last evening, when a large party of young people strolled to the delightful resort and feasted on seasonable refreshments until a late hour."

Rouss Spring was purchased by the city of Winchester in 1890, and it supplied the city with water for many years.

*

Winchester Downtown - where fighting occurred the first time.

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There were (at least) six major battles in Winchester,VA. The visitors center at Third Winchester has signs for all six. Here's W1. 

https://www.hmdb.org/m.asp?m=155108

The First Battle of Winchester

May 25, 1862

—Stonewall Jackson's Valley Campaign—

"Our entrance into Winchester was one of the most stirring scenes of my life."

—Confederate Gen. Thomas J. "Stonewall" Jackson, Remembering the reaction when he entered Winchester after the battle

At the First Battle of Winchester, Confederate Gen. Stonewall Jackson flanked and routed Union Gen. Nathaniel Banks smaller force, sending the Federal defenders tumbling out of the city — and out of the Valley — with most civilians welcoming Jackson and his men as liberators. Jackson's smashing victory was the emotional high point of his famed Valley Campaign.