DO NOT ATTEMPT WITHOUT A GPS or MAP/COMPASS. Trail is poorly marked and hard to find. We attempted to do the lollipop in 2 days. We started off west on the north loop and camped at Bliss Springs. It was a strenuous but doable stretch, and the views were nice.
On the second day, we completely lost the trail past Fiddler's Spring. That region has very little water in the early fall, and the terrain becomes difficult to walk through. We were forced to make camp for a 2nd night inside the valley because it would've been too dangerous to go off trail at night in the hilly terrain.
On the 3rd day, we abandoned attempts at finding the trail again, and went bush whacking, going NE out of the creek bed. We found intermittent stretches of what looked like trails, but they were unreliable to follow. We eventually cut north enough to rejoin the northern loop and found our way back to the trail head.
Oh, there's a free tent along the trail if someone wants it... Good luck.
Another one we did not actually complete but did a couple miles of, not far enough up to catch any of the interesting sites. Still, nice area, lots of hickory forest and limestone. Typical features of Ozark forests. Been a few years, but I do recall almost losing the trail a couple times and agree it's not always clearly marked.
Do not plan to do this trail In two days. I normally hike an average speed of 2.5 miles with a full backpack weighing around 35 pounds. I set out to hike this trail over a weekend. I arrived at the trailhead at 10 AM in the morning at five pond . I chose to hike the trail clockwise. The first sign showed approximately seven miles to the float camp. Saturday went pretty good. The trail was not well blazed. However, I could follow the depression of the trail in the leaves. I lost the trail a couple of times and had to Bush wack. But I did see both fiddlers ring and white Creek Cave. I arrived at float camp at 4:30 in the afternoon. That's gave me plenty of time to set up camp and start a fire in the fire ring . Sunday was a different story. I started out on the trail and then quickly lost it I bushwhacked more than I hiked on the trail. It took me five hours to go for miles to Bliss Springs . That left me with 8 miles to get back to camp five pond. It was now 1:30 in the afternoon. Sunset was at 5 PM. This left me with four hours of light . If I had been on a trail, and averaging 2 mph I could have made it back to camp Sunday night . At 4 PM it became clear that I was not going to make it back to camp before dark going cross country. Without a trail it would be very difficult to navigate with a headlamp going cross-country. So I took an alternate course and followed an old logging road that led me up to the town of wilderness. I then hiked on the forest Service Rd. to get back to camp five pond. So basically after you hike from camp five pond to the float camp, you are pretty much on your own going cross-country. Be sure and have a good map and GPS unit. There is no phone connection for most of the trail. The topo map that I had from all trails did not accurately reflect the actual trail . I I attempted to follow the trail shown on the topo map and in most instances you will see where my track across the trail there was no trail . The highlights of the trip would be bliss spring. Other than that there were not any scenic overlooks to speak of. Just another typical hike in the Missouri hardwood forest. Except there was no trail to follow. If you follow my track you will get back to camp but it is approximately 22 miles and it will take you around 18 hours to complete. I hiked for six hours on Saturday to get from camp five pond down to the float camp. However, I hiked 13 hours on Sunday going cross country. I averaged less than a mile per hour. It maybe easier to follow the trail when the leaves are off the trail. Did I mentioned poor blazing. If you go, good luck.