My family is from Silver Spring, although I grew up in Glenmont. I still enjoy going back there even though all the family has moved out or passed on. Maybe if I ever get the Classic up that way we'll get together.
Since I don't ride the Interstates, and really look for slower backroads riding, Silver Spring (where I actually bought my 2023 Classic) is not a good spot to head to as I'd be looking at about 3 1/2-4 hours of round trip before any hooking up to ride would happen.
Maybe someone(s) in the Carroll/Baltimore/Harford county sphere is out there?