JB is great. The event always has a fun surprise, like one year a banjo player serenaded us up a steep gravel climb.
Wintergreen is a fun/painful event, like you said. Here’s the route: Wintergreen 2019 | Strava Ride Segment in
Typically it’s in May of each year. It’s called the James Beazell Hill Climb, and it’s advertised on the website or Facebook page of the Charlottesville Bicycling Club.