Winchester's oldest house, built 1754 by Quaker settlers — a six-foot woman who posed as a Civil War teamster and a gentleman in Quaker dress haunt its limestone walls
1340 S Pleasant Valley Rd, Winchester, VA 22601
Research updated June 2026
Age
All Ages
Cost
$
Adults $6, seniors $5, students K–12 $3, children under 5 free
Access
Limited Access
Two-story limestone structure; stairs required for upper floors
Equipment
Photos OK
Est. 1754 · Oldest House in Winchester · Quaker Settlement History · Hollingsworth Family · Civil War Shenandoah Valley · Virginia Landmarks Register
Isaac Hollingsworth and his family were among the earliest Quaker settlers in what is now Winchester, Virginia, arriving in the lower Shenandoah Valley around 1728 with a 582-acre land grant. His son Abraham built the two-story limestone house in 1754, selecting a site beside a natural spring. Abraham reportedly described the property as 'a delight to behold' — the phrase that became the house's name. The log cabin adjacent to the main house predates the limestone structure and served as the family's initial shelter.
Five generations of Hollingsworths occupied the property over roughly 180 years. The family's Quaker identity shaped the house's austere character; the thick limestone walls and simple proportions reflect the plain style favored by the Religious Society of Friends in colonial Virginia.
During the Civil War, Winchester changed hands more than seventy times as Union and Confederate forces contested the Shenandoah Valley. The Hollingsworth property suffered during the repeated occupations — livestock were seized and the grounds were used by both armies at various points. A later family member, Mary Hollingsworth, who died in 1917, is documented in family accounts as having disguised herself as a man to operate a supply wagon during the war to earn income for her family.
The Winchester-Frederick County Historical Society opened the house as a museum in 1961 following restoration work begun in 1951. It was listed on the Virginia Landmarks Register and the National Register of Historic Places as part of its preservation record.
Sources
The hauntings at Abram's Delight are reported by people who work in the building rather than by tourists seeking them out. The primary figure is Mary Hollingsworth, who died in 1917 after a life that included, by family account, operating a supply wagon while disguised as a man during the Civil War to support her family financially. She was described as a masculine woman standing six feet tall.
Staff reports describe objects moving without explanation — vases knocked from shelves, furniture displaced, the sound of breaking glass with nothing found broken afterward. Appliances and stereos have been reported switching on independently. Dogs brought into the building reportedly refuse to climb the staircase toward the upper floors. No injuries have been associated with the activity.
The second figure is older and less associated with specific incidents. During the 1951 restoration, carpenters working on the house described seeing a tall man in Quaker-style clothing and a broad-brimmed hat walk up the front steps, enter the building, and emerge again roughly ten minutes later. The figure was consistent in description across multiple workers. Subsequent visitors have reported similar sightings at the front entrance.
Notable Entities
The Winchester-Frederick County Historical Society leads guided tours of the 1754 limestone house and adjacent log cabin, covering five generations of Hollingsworth family history, Quaker settlement in the Shenandoah Valley, and the home's Civil War context. Group, school, and bus tours are welcome.
Every HauntBound history is researched from documented sources. We clearly separate verified historical fact from paranormal folklore.
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