Winchester sits at the top of the Shenandoah Valley, a small city with a disproportionate amount of American history packed into its streets. George Washington got his start here — surveying, building forts, winning his first election — and during the Civil War the town changed hands between Union and Confederate forces so many times that locals lost count. Six battles were fought in and around Winchester, and the city is said to have changed flags around 70 times over four years.
The historic downtown is well-preserved and walkable. Stonewall Jackson's headquarters on North Braddock Street is open as a museum in warmer months. Abram's Delight, a 1754 stone house furnished with 18th-century pieces, is the oldest house in the city. The National Cemetery and Confederate Cemetery hold thousands of Civil War graves. George Washington's office, where the young surveyor worked for Lord Fairfax, still stands.
Winchester is also apple country — the surrounding orchards make it one of the largest apple-producing areas in Virginia. Every spring, the Shenandoah Apple Blossom Festival draws over 250,000 visitors for parades, music, and the world's largest firemen's parade. The Wayside Theatre in nearby Middletown runs a summer and fall season of plays.
The Shenandoah Valley stretches south from here, and Winchester makes a natural starting point for exploring the region's battlefields, caverns, and mountain scenery.