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Few American towns changed hands as often as Winchester: during the Civil War control of this crossroads at the top of the Shenandoah Valley switched between Union and Confederate forces dozens of times. Long before that, a young George Washington worked here as a surveyor and militia commander, building Fort Loudoun and winning his first election to the House of Burgesses from Frederick County.
Today the old town is a walkable grid of brick and limestone buildings centered on the Loudoun Street pedestrian mall, with the Old Court House Civil War Museum, Stonewall Jackson's wartime headquarters and Washington's small log office all within a few blocks. Country music fans come to see the modest house where Patsy Cline lived before she became a star.
Winchester is also the heart of Virginia apple country, celebrated each spring at the Shenandoah Apple Blossom Festival. The Museum of the Shenandoah Valley, with its historic house and gardens, battlefield trails and orchards on the edge of town round out a visit, and Skyline Drive is under an hour south.
Several car-free blocks of Loudoun Street in Old Town Winchester, lined with 18th- and 19th-century buildings that now hold restaurants, bookshops, galleries and boutiques. Outdoor dining and summer concerts keep it lively into the evening. Park in one of the downtown garages and explore everything else on foot.
A regional museum telling the story of the Shenandoah Valley through art, decorative objects and changing exhibitions, set beside the Glen Burnie Historic House and its six acres of formal gardens. Spring blooms make the gardens a highlight. Allow at least two hours, and note that the house and gardens open seasonally.
The 1840 Frederick County courthouse served as a hospital and prison during the Civil War, and soldiers from both sides scrawled graffiti on its walls that you can still read today. Displays of weapons, uniforms and personal items tell their stories. It faces the Loudoun Street Mall, so pair it with lunch nearby.
A small log and stone building that a young George Washington used as his office in the 1750s while overseeing construction of Fort Loudoun during the French and Indian War. Exhibits show surveying tools and frontier artifacts from his years here. It is open seasonally; a combined ticket covers other city museums.
The Gothic Revival house where General Thomas "Stonewall" Jackson made his headquarters in the winter of 1861-62 while planning his famous Valley Campaign. His office is furnished as it looked then, alongside Civil War artifacts and personal items. Guided tours run seasonally and last about 45 minutes.
Winchester's oldest house, a limestone home built in 1754 by Quaker settler Isaac Hollingsworth beside a spring-fed pond, furnished with 18th- and 19th-century pieces. A reconstructed log cabin stands on the grounds. Tours run seasonally, and the pond-side lawn next to Jim Barnett Park is pleasant for a picnic.
The modest two-story house on South Kent Street where Patsy Cline lived with her family from 1948 to 1957, before she rose to fame with songs like "Walkin' After Midnight." Guided tours share stories of her early life and career, with photos and memorabilia. Open seasonally; tickets are sold on site.
A Beaux-Arts library opened in 1913 with a copper-clad dome, ornate stonework and a light-filled rotunda with glass floors in the book stacks. It still works as the city's main public library and houses a respected archive of local history. Visitors can step inside during opening hours to admire the reading rooms.
A huge spring festival held since 1924, with a grand feature parade, firefighters' parade, bands, a coronation of Queen Shenandoah, a 10K race and events across town over about ten days in late April and early May. Book lodging well ahead, as hotels fill months in advance, and arrive early for parade viewing.
Preserved fields and woods on the northeastern edge of the city where Union forces under Philip Sheridan won the 1864 Third Battle of Winchester. Several miles of walking and biking trails pass interpretive signs explaining troop movements. Admission is free; trails are open daily from dawn to dusk.
Winchester's largest park, with walking paths, sports fields, an outdoor pool, playgrounds, tennis courts and picnic shelters spread over rolling lawns. It hosts many community events and festival activities. Free parking makes it a handy family stop between museum visits in Old Town.
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