The town of Woodstock in the Shenandoah Valley of Virginia is home to a limestone courthouse that's been in use since 1795, making it the oldest working courthouse west of the Blue Ridge Mountains.
Woodstock has a cute array of shops and places to eat, an art and pottery studio, and a brewhouse and vineyard. Head up to the Woodstock Tower Observation Site, built in 1935, it has a stunning 360-degree view of the town and surrounding countryside. Nearby George Washington National Forest has a great selection of trails and hikes.
Summertime is peak tourist season in Woodstock, so consider coming in late Spring to get the great weather without the crowds.