Caudill Cabin via Basin Creek Trail and Grassy Gap Fire Road
This is a moderate out and back trail to Caudill Cabin near the Blue Ridge Parkway.
The trail branch off of the fire road and quickly becomes primitive with little blazing. It's fairly easy to follow, but there are a total of 34 creek crossings that can be intense after rains, during snow melt, etc. The trail is only blazed at the creek crossings and they're not always easy to locate. Mapping seems to show the trail not always crossing the creeks and can be confusing to some.
Park at the lot on Longbottom Road. It's an easy start up the firewood to the Basin Creek Trail. This makes for a nice day hike.
Or, park along the Blue Ride Parkway and hike down Blue Ridge Primitive Trail. It'll deadend at the Basic Creek Trail. This will make for a very long and difficult day hike.
This is a tough hike in general. Hike at your own risk and make wise decisions based on the capabilities of yourself and your child.