Spend hours wandering 250-year-old shady brick streets in its 45-block historic district — stopping in at the Old Court House — or checking out Gaunt's Drug Store, where Patsy Cline worked before heading for Nashville fame.
Winchester and Frederick County were the scene of six major battles during the Civil War, and the city itself changed flags some 70 times during the four-year conflict.
But Winchester isn't just a haven for history buffs. The dozens of small towns that dot surrounding Frederick and Clarke counties offer bucolic bliss: Enjoy miles of rail fences, apple and peach orchards, and lovely stone houses from the 18th and 19th centuries.
When Daisy Goodwin, 71, first discovered the area in the 1980s, she says, "I didn't think I could ever live somewhere so rural, after having grown up in the suburbs and city. It was such a different world — slower-paced and rustic."
But the area's beauty really sold her, and she built a house in nearby Gore in 2004. It's not all agrarian, though, and downtown Winchester offers plenty to do: Goodwin is fond of meandering through the town's galleries, or people watching at Jim Barnett Park.