VA250 Historic Winchester 

Celebrating 250 Years of Virginia History

Friday

MIDDAY
Arrive in Winchester and begin your VA250 journey at the Winchester-Frederick County Visitor Center, where you can pick up maps and historic guides highlighting Winchester’s role in Virginia’s 250-year story. Start with a walk through the Old Town Winchester Historic District, one of the oldest continuously occupied commercial districts in Virginia and a key crossroads in colonial and early American history. Stroll the pedestrian mall’s brick-lined streets, historic storefronts, and locally owned shops before heading to your hotel to settle in.

EVENING
Kick off your weekend with a guided historic walking tour of Old Town Winchester, focusing on the city’s colonial roots, its strategic importance during the French & Indian War and the Civil War, and the people who helped shape Virginia’s past. Enjoy dinner at one of the locally owned restaurants along the pedestrian mall, surrounded by buildings that date back more than two centuries.

Saturday

MORNING
Begin the day at George Washington’s Office Museum, a cornerstone of Virginia’s pre-Revolutionary history. Learn how a young George Washington worked here during the French & Indian War, gaining leadership experience that helped shape the future first president of the United States. Continue to Abram’s Delight, Winchester’s oldest surviving home, offering insight into 18th-century frontier life in the Shenandoah Valley. Next, visit the nearby Hollingsworth Mill, an early 19th-century industrial site that reflects the region’s growth and ingenuity.

AFTERNOON
After lunch downtown, head to the Museum of the Shenandoah Valley, where art, history, and landscape come together. Tour the Glen Burnie House, home of museum founder Julian Wood Glass Jr., explore exhibits that tell the story of the Valley from Native American settlement through modern times, and stroll the beautifully designed gardens. If time allows, add a visit to the Hexagon House, one of only a few six-sided homes in the nation, or tour the architecturally significant Handley Regional Library, a Winchester landmark funded by philanthropist Judge John Handley.

EVENING
Continue your VA250 experience with a visit to Stonewall Jackson’s Headquarters Museum, where General Jackson lived during the winter of 1861–62. The site offers insight into Winchester’s pivotal role in the Civil War, as the city changed hands more than 70 times. Enjoy dinner at a local restaurant and conclude the evening with a leisurely stroll through Old Town, where historic buildings are beautifully illuminated after dark.

Sunday

MORNING
Start your morning with coffee and a pastry at a downtown café before traveling to the Third Winchester Battlefield (Opequon). Walk the self-guided trails through this preserved landscape and learn about the 1864 battle that helped secure the Shenandoah Valley for the Union, influencing the outcome of the Civil War and the future of the nation.

AFTERNOON
Before departing, visit Mt. Hebron Cemetery, where veterans from multiple American conflicts—including the Revolutionary War, War of 1812, and Civil War—are laid to rest. Explore the historic sections and monuments that reflect over 250 years of Winchester and Virginia history. End your stay with lunch at a local favorite or farm-inspired restaurant, departing with a deeper appreciation of Winchester’s enduring role in the Commonwealth’s past and the nation’s founding story.