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I just got back from a 3 day trip in Cumberland Gap.
Great little trip. First day I hiked from the pinnacle on the Ridge Trail to the junction with the Sugar Run trail. I took that down and back up again. The Sugar Run trail reminded me a lot of the Road Prong trail in the Smokies, just on a smaller scale. Once back at the trail junction, I took the Ridge Trail to Gibson Gap. Great little campsite with a spring close by, views over the nearby ridge, and a nice little rock overlook. 10 miles or so? The next day I headed out along the Ridge Trail. The fog got thicker as I went on, and by the time I reached the junction with the Hensley settlement spur trail, I was pretty well enveloped. I camped that night at White Rocks. 11 miles that day I think. The last day I checked out the White Rocks overlook and Sand Cave. I was actually planning on spending at least one more night in the park, but I decided early on to just make a go for it and try doing the whole thing straight through, so I just did it, 20 miles in all. The first 15 were great, the last 5 weren't. This park allows horses on almost all of the trails, and I was lucky to have gotten out earlier in the year. The trails weren't in too bad of shape, but I wouldn't try going back much later in the year.