The trail was a little bit washed out/muddy when we were hiking it, but since it's quite wide it was easily navigable and you won't get lost as it's clearly marked. We used the the Wilderness Road trail. On the trail, you get to pass through the "saddle" AKA the actual Cumberland Gap itself. It's a pass that was used as a trail and key passageway through the lower central Appalachians since the surrounding mountains are difficult to pass. There's a sign right at the saddle. At the peak/end of the trail, there is a gazebo with benches around the border markers. You can take in the views and stand in three states at once! It's a neat experience.
Just make sure to bring water, hats/sun protection, and good shoes! read more