The area that is currently Winchester, Virginia was of vital significance long before Europeans entered the region. Legend states that the Shawnee migrated into Virginia’s Shenandoah Valley and established settlements and tribal headquarters where Winchester is today. Their campgrounds were along a well-traveled Indian trail and buffalo migration route, later known as The Great Wagon Road. Because the trail was an indigenous trade route the language of the Shawnee was widely spoken while trading among tribes and when Europeans appeared the Shawnee were called upon to be translators. Because of their contact with both natives and Europeans they also became a force in resisting westward expansion. #discoverwinchesterva
Early European contact was with 70 families of Pennsylvania Quakers in 1732. They started a colony they named Hopewell after their previous home in Hopewell in Lancaster, PA. In 1744 Colonel James Woods founded Winchester on a Lord Fairfax land grant making Winchester the oldest city in Virginia west of the Blue Ridge Mountains. Located at the intersection of east and west and north and south roads Winchester is filled with routes that provide easy access to sites, activities and experiences and help visitors navigate the city and surrounding area to create a personalized adventure.
The award-winning Winchester-Frederick County Visitors Center is a mandatory first stop. It offers maps, brochures, and a series of orientation galleries that make planning easier. An orientation video introduces visitors to the county and a Civil War Orientation Center includes a brief film on Winchester’s role in the war. The Patsy Cline Exhibition tells the story of Winchester’s favorite daughter’s youth with memorabilia, photographs and text. The Gift Shop stocks books, apparel, local beer, wine, souvenirs and locally crafted products and an exterior picnic area and playground adjoin Jim Barnett Park and Wilkins Lake.
Colonial Winchester was a frontier settlement that played an important role in the nation’s early history. Redheaded 16-year old, George Washington arrived in 1748 to survey the land for Lord Fairfax and the Walking Washington’s Winchester tour includes 15-sites that were important in his life from 1748-58.
Fort Loudon was built from 1756-58 under the command of George Washington for protection during the French and Indian War. The site may be visited but only a bastion and a limestone well remain.
While designing and supervising the construction of the log fort Washington worked from a nearby office. Rooms inside the office museum contain relics from the French and Indian War, American Revolution and Civil War and artifacts and maps representing Washington’s years as a surveyor. Display highlights include a colonial jail door and accompanying key. Two French and Indian War cannons and a sculpture of Washington are on the exterior.
Abram’s Delight is the oldest extant house in the city. The 1754 house has been restored and furnished in the style of the 1700s. Tours are offered.
Winchester’s African American Heritage self-guided driving tour lists 28 sites of significance within the city and three in the surrounding area. The tour advances largely through use of biographical stories of the blacks that lived and worked there. There were not the types of large plantations found in the South and most enslaved workers functioned as domestic, manual and industrial laborers. A limited number of African Americans were free and the percentage was larger than that of the state.
Belle Grove Plantation was built on what had been a Native American hunting ground prior to European ownership in 1685. The Classic-revival manor house was constructed of limestone from 1794-97. The plantation was originally 7500-acres and was the 2-story home of Major Isaac Hite Jr. and Nelly Madison, sister of President Madison. The mansion’s interior paint, woodwork, carpeting and glass have been restored. A property tour includes the original icehouse, smokehouse and unique fieldstone marked slave cemetery.
After seven-years of research about the property an exhibit, Unearthing Enslaved Lives, opened. Documents revealed that in 1810 there were 103 enslaved, 101 in 1820 and in 1824 sixty were sold. Many of the enslaved were children and there is speculation that Belle Grove may have been a breeding plantation. There is an orientation video and numerous displays and artifacts.
The plantation was the site of the Battle of Cedar Creek in 1864 and Union General Sheridan headquartered here with some of his 31,600 troops bivouacked on the lawn. In 1885 the first Civil War reunion was hosted here. Belle Grove opened for visitors in 1967.
The Civil War cut a wide path through Winchester. Six major battles were fought there and the city changed hands more than 72 times. The Shenandoah Valley was strategically important because it was considered the “bread basket” of the South because of its abundance of crops, mountains that could provide cover and roads that lead directly from the north to the south.
Heyward Shepherd, a free black man from Winchester, worked as a railroad porter in Harper’s Ferry. He was the first to be killed, shot in the back by a raider, during John Brown’s Raid.
The 1862 First Battle of Kernstown was General Thomas "Stonewall" Jackson's sole battle loss. In 1863 Jackson was mortally wounded and Winchester physician, Dr. Hunter McGuire amputated his arm and ministered to him until he died. Stonewall Jackson’s Headquarters from Nov. 1861-March 1862 is currently a museum. Exhibits include Jackson memorabilia and Civil War artifacts.
Enslaved Thomas Laws possessed a pass to cross Confederate lines to sell vegetables in Winchester. Laws was also a messenger and spy, carrying messages between Union General Sheridan and Quaker spy Rebecca Wright. Their information led to an attack on General Early in 1864 that led to the end of Winchester’s Confederate occupation.
Spottswood ‘Spots’ Poles was born in Winchester in 1887. From 1906-1923 he played for the American Negro League and turned pro in 1909 when he began playing with the Philadelphia Giants. His career continued with the New York Lincoln Giants where he was known as the “Black Ty Cobb”. In the midst of his career he enlisted in the army and served as a Harlem Hellfighter earning five Battle Stars and a Purple Heart. His lived at 530 Fremont Street.
Country music legend Patsy Cline was born in Winchester’s Memorial Hospital. She and her family moved around with the Patsy Cline Historic House being their 19th move in 16-years in 1948. Originally a 3-room log cabin Patsy, her sister, brother and mother lived there. Guided tours of the restored home include personal items, photographs, stage attire and stories about her life and career. Patsy died in a plane crash in 1963.
One of the most unique trails is the Winchester Service Station Grub Trail, designed to highlight active
and repurposed gas stations with great ambience and delicious food. Bonnie Blue Southern Market & Bakery has been recognized by the NY Times as one of 13 essential barbeque stops. Riley’s ChiCorkfish serves chicken, cow, pork and fish, their motto, “it is who we are and what we fix”. There are more than six to select from.
For the more active traveler the Virginia Birding and Wildlife Trail is a wonderful option. There are more than 178-miles of trails in the National Forest, some handicapped accessible. The county also has 31-miles of trout streams. @visitWinchesterva
Select from the menu of Winchester wonders and craft your special adventure.
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