Alpine Loop

Alpine Loop Gran Fondo is a mixed surface premier cycling event in the beautiful Shenandoah Valley. It has something for riders of all abilities with option for paved shorter routes.
The Alpine loop namesake has a lot of climbing 10,000 + feet and is inspired by the rugged mountain roads that border Virginia and West Virginia and features timed sections and 25% gravel roads. This event has become a mid Atlantic classic. And has its own style!

Most riders opt for 30-35c gravel and wide clearance road bikes with compact gearing.

https://alpineloopgranfondo.com/routes/

Hotel Madison is closest to the start there are plenty of options tho.