The Wilderness Road Trail at Cumberland Gap National Historical Park near Cumberland Gap, Virginia is an easy 1.4 mile out-and-back hike that leads from the Daniel Boone visitor center west toward the Gap Cave Trail and the Tennessee Road Trail to the Iron Furnace.
This trail is flat and easy with not much elevation change, but there are a couple of waterfalls along the way. You'll pass a creek that spills over the trail - there's a bridge you can use to cross it and waterfalls to each side; however, during the summer the waterfalls are hard to see without hiking down the hill to get a closer view. The waterfalls looked to be about 10 feet in height or more, but it was difficult to tell at the time.
Biking and dogs are allowed here.