The biggest event in this quaint town is the Apple Blossom Festival. Running from the last week in April through the first weekend in May, this annual celebration of Winchester’s star crop features concerts, speakers and a five-hour parade. If you’re not in town for the Apple Blossom, there’s still plenty to do. Stroll the brick and cobblestone pedestrian downtown mall of Old Town Winchester – if you’re in town on a Friday, you’ll enjoy the First Fridays Art Walk. While downtown, window shop at crafts and antiques stores and dine at local favorites like the Village Café and Bistro, which offers a wide variety of craft beers, wines and comfort fare, or sit by the fireplace at the more upscale Village Square Restaurant. Just outside of downtown, your last stop should include the impressive Museum of the Shenandoah Valley, where you can view exhibits like ‘Becoming Patsy Cline’ or learn some of the history of this beautiful region.