About Cumberland Gap -
Unfortunately when they built the tunnel under the gap - they closed the old highway. Cyclists aren't allowed in the tunnel and are banned from the trail that has replaced the old highway. I have been in touch with the park service about this but they seem intent on "restoring" the gap to how it appeared ion Boone's day - excluding, of course, the highways you can see and the road to the overlook that you can drive up on. They just don't get it.