Lookout Point - Centennial Trail Loop is a 4 mile loop trail located near Custer, SD and is good for all skill levels. The trail is primarily used for hiking and is accessible from April until October.
I did the Centennial Trail for a short time starting from Badger Hole. It is a lovely hike up and down through the woods. The trail gets very narrow at times, so long pants are advisable. Some parts are rocky. Saw several deer and came up to a 360 lookout point. I recommend this trail if you enjoy hiking through the woods for extended periods, meaning not expecting to arrive at a peak.
Nice hike through the prairie hills. NOTE: trail 4 takes a hard right across a small creek about 1/4 mile in, next to trail marker. Lots of people must miss this (we did) evidenced by clear path through unmarked trail. Fortunately after a mile you do end up at centennial trail. Saw several prairie dog towns and bison. You need to be aware of surrounding as were hiking along a herd of bison came crashing down a wooded hill across the trail and up another hill. They came across trail just 30 yards ahead of us.
This is an easy to moderate trail. It combines the Lookout Point trail (number 4 in the Wind Cave National Park) with the last part of South Dakota's Centennial Trail to form a loop. The trail is easy if you travel counter clockwise -- starting on the Lookout trail. A little over 2 miles in you will descend into a series of small valleys. This is a steep descent going counter clockwise, but a steep ascent going clockwise. The Lookout trail takes you across a stretch of prairie, including through a dozen or so prairie dog communities. There is also evidence of bison activity. If you hike in the early evening, you could run into elk coming down from the hills into the valleys about halfway into the hike. We did not see any elk, but we came across a resting bison and a bison carcass. Just after the Lookout and Centennial trails meet, look for the cave on the left where much of a stream ends up. Also. the trail ends on a short but steep incline. Be alert; while the trail is marked some parts have grown over and/or gotten mixed up with elk and bison trails.