76 miles W of Washington, D.C.; 189 miles NW of Richmond
To paraphrase Abraham Lincoln's Gettysburg Address, it is altogether fitting that Winchester comes first in my descriptions of the valley's towns, for its excellent Museum of the Shenandoah Valley provides an altogether fitting introduction to this area. Especially if you're arriving by car from the north or from Washington Dulles International Airport, Winchester should be your first stop.
Winchester is also known as Virginia's "Apple Capital," so-called because of the number of apple orchards in the northern end of the valley. The Shenandoah Apple Blossom Festival in May is one of the region's most popular events.
What is now Winchester was the site of a Shawnee Indian campground before Pennsylvania Quakers settled here in 1732. George Washington set up shop in town during the French and Indian War 20 years later, and his office is still here. Thanks to its strategic location, Winchester changed hands no fewer than 72 times during the Civil War. Both Confederate Gen. Stonewall Jackson and Union Gen. Philip Sheridan made their headquarters here at one time or another. It is still a major trading post, as the busy roads leading into and out of Winchester's central Old Town will attest.
Give yourself at least a morning or afternoon here to visit the Museum of the Shenandoah Valley, Washington's office, and Stonewall Jackson's headquarters. If you're a country music fan, you can drive by Winchester native Patsy Cline's old haunts and visit her gravesite on the edge of town.