Set against the backdrop of Virginia’s Shenandoah Valley, this rally is all about epic rides, rich history, and unforgettable scenery. Choose from more than 40 routes through Virginia, West Virginia, and Maryland, with opportunities to collect H.O.G. check-ins, explore Civil War sites, and take in iconic stretches like Skyline Drive and the Blue Ridge Mountains. From the winding roads and breathtaking overlooks to underground adventures at Luray Caverns and lively walking poker runs downtown, every ride offers something new to discover.
Rally Package Options
Orange Package – $40
Includes Rally Wristband, commemorative rally T-Shirt, pin and patch
Orange Package registration closes 5/19/2026
Black Package – $30
Black Package includes Rally Wristband, pin and patch
Black Package registration closes 6/16/2026
Both packages include a great riding adventure on the Parkways!
More Information and Event Schedule
Winchester’s Skyline Harley-Davidson dealership will be hosting the Demo Truck!
If you’ve been waiting for the perfect moment to throw a leg over a new Harley-Davidson… this is it. The Harley-Davidson Demo Fleet is rolling into Winchester, VA during the rally for FOUR full days, bringing riders the ultimate opportunity to experience the newest machines like never before.
NOTE: YOU DO NOT NEED TO BE ATTENDING THE RALLY TO SIGN UP FOR A DEMO TRUCK TEST RIDE! ALL ARE WELCOME.
More Information on Skyline Harley-Davidson