Last fall, when I section hiked through that area (Erwin to Damascus), I left my car for one day at Hughes Gap, just south of Roan Mt, and had no problem at all. The ATC Guide for TN/NC lists the directions to get there on pg. 108 - but does say that āVandalism to cars parked overnight at Hughes Gap is common.ā Maybe itās the overnight issue thatās the problem, but I was fine. Thereās room for only 3-4 cars there and itās pretty remote so I wasnāt worried.
From there, youād have a nice 9-1/2 mile hike up and over Roan High Knob and the Humps to Overmountain Shelter and the next day, 8.2 miles to Applehouse Shelter. On the 3rd day, you could walk down to 19E and get to your car stashed in town somewhere (NOT at the trail crossing.) Or you could have a short 1st day and stay at the Roan Mt. Shelter, then OverMountain, with a longer 3rd day from Overmountain to the car.
The parking problem on the north end of the section seems to be a lot more serious than the south end but there is more ācivilizationā there and presumably you could make an arrangement with a local business down the road from the trail along 19E.
Using a shuttle driver defeats the benefit of having two cars, but if you were to go that method: Bob Peoples at Kincora Hostel at Dennis Cove Road is closer to where you want to end up. Both Bob and Sutton are fine gentlemen and you wouldnāt go wrong working with either.
Have a good hike - thatās a really nice section.
Happy Trails -
Capt. Bly
Capt. Bly