Abram’s Delight, the oldest dwelling in Winchester, stood in the path of the First Battle of Winchester on May 25, 1862, and experienced the passage of both Union and Confederate armies during the war, yet survived and now illustrates the civilian side of the conflict. Mary Hollingsworth and her siblings, Jonah and Annie, occupied the house during the war. According to local tradition, Mary Hollingsworth, who stood more than six feet tall, may have impersonated a man to spy for the Confederates. She also gave meals and shelter to Union soldiers on several occasions. Early in the war, a soldier wrote to her household, “My best wishes to all at your house, and all those who were there during my stay with you.” In the spring of 1865, William Darnel of the 3rd West Virginia Cavalry thanked her for her hospitality, writing, “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, and 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, but the commission denied her request, stating that the damage occurred as result of the “fortunes of war.” Built in 1754 by stonemason Simon Taylor for Isaac Hollingsworth, Abram’s Delight was named for Hollingsworth’s father, Abraham. The two-story wing was added about 1800, and the original woodwork was replaced in the Greek Revival style in the mid-19th century.
