Explore Old Town Winchester, Virginia
Winchester, Virginia, stands as the oldest city in Virginia west of the Blue Ridge Mountains. The historic district, recognized as Old Town Winchester, comprises a delightful four-block pedestrian-only region adorned with beautifully restored Federalist-style architecture, unique restaurants, shops, and significant historic landmarks.
Abram’s Delight Museum
Abram’s Delight, dating back to 1754, is Winchester’s oldest house and served as the home to five generations of the esteemed Hollingsworth family. As one of the first early settlers, Abraham Hollingsworth established one of the Valley’s first grist mills and his home doubled as the area’s first Quaker meeting house. Today, this historic site operates as a museum and features an array of 18th-century art and antiques that narrate the history of early Shenandoah Valley settlers.
Address: 1340 S. Pleasant Valley Road (540) 662-6519. Located adjacent to the Winchester Visitor Center and Shenandoah University, about 1.5 miles southeast of Old Town.
Abram’s Delight Cabin
This log cabin, situated on the west lawn of the Abram’s Delight Museum, dates back to 1780. Although it is not the original structure, it closely resembles the style of the time and was reconstructed on the premises in 1967. Visitors can admire the cabin as part of the tour of the main house.
George Washington Statue
Situated outside George Washington’s Office Museum in Old Town Winchester, this statue commemorates George Washington’s connection to the area. During his time, Washington utilized a small log building in Winchester as a military office while overseeing the construction of Fort Loudoun. The building is now a museum that showcases Winchester’s importance in the early military and political career of our nation’s first president.
Address: 32 West Cork and Braddock, Winchester, VA
Shenandoah Discovery Museum
The Shenandoah Discovery Museum serves as an engaging children’s activity center, providing various interactive exhibits and programs focusing on sciences, mathematics, humanities, and the arts. It is conveniently located on Loudoun Street in the heart of Old Town Winchester.
Address: 54 S Loudoun St, Winchester, VA
Website: discoverymuseum.net
Fort Loudoun
Fort Loudoun played a crucial role as the command center for the Virginia Regiment during the French and Indian War. Named after John Campbell, Earl of Loudoun, this square fortification was designed by George Washington, who commanded the Virginia regiment. A historical marker located between the sidewalk and fenced yard describes the fort’s significance in American history.
Winchester City Hall
The Winchester City Hall, constructed in 1900, received half of its funding from local resident Charles Broadway Rouss.
Old Court House
The Old Court House in Old Town Winchester has a poignant history, having served both as a hospital and a prison during the Civil War. Today, this historical site is home to a nationally recognized collection of Civil War artifacts and offers tours of the building.
Address: 20 N. Loudoun Street, Winchester, VA
Website: www.civilwarmuseum.org
Handley Library
The Handley Library is renowned for its beauty, showcasing the Beaux-Arts architectural style. Opened in 1913, the library is a result of generous funding from Judge John Handley of Scranton, Pennsylvania, aimed at establishing a public library for the community.
Address: 100 W. Piccadilly St. Winchester, VA
Website: www.handleyregional.org
Union Jacks
Located in the historic Union Bank Building from 1878, Union Jack Pub & Restaurant offers a delightful dining experience featuring authentic British cuisine in a cozy pub atmosphere. It stands out among the excellent dining options on the Loudoun Street Walking Mall.
Address: 101 N Loudoun St. Winchester, VA
Website: theunionjackpub.com
Shenandoah Valley Museum
Situated just outside Old Town Winchester, the Museum of the Shenandoah Valley highlights the rich art, history, and culture found within the region. Additionally, the museum complex features the Glen Burnie Historic House and Gardens, once home to Colonel James Wood, who settled in this land in the early 1700s and generously donated part of his property to establish the city of Winchester in 1744.
Address: 901 Amherst Street, Winchester, VA
Website: www.shenandoahmuseum.org
Glen Burnie Estate
On the grounds of the Shenandoah Valley Museum, the Glen Burnie Historic House and Gardens offer visitors a chance to explore six acres of scenic gardens surrounding the main house.
Address: 901 Amherst Street, Winchester, VA
Website: www.shenandoahmuseum.org
