Ozark Trail, Missouri
Taum Sauk section; 36 miles, point to point
This section of the Ozark Trail, two hours south of St. Louis, crosses through the heart of the 1.4 billion-year-old St. Francois Mountains, covered in an oak and hickory forest that lights up come fall. The trail is impressively rugged, and you'll need at least four days to complete it. But the sites are worth the effort. "You'll pass Mina Sauk Falls, which is a series of cascades 132 feet high," says Matt Atnip, of the Ozark Trail Association, "and Devil's Tollgate, where the trail threads through 30-foot-high volcanic rock walls — it's like walking through to Middle-Earth."
How To Do It: Backcountry camping is allowed most places along the route but, says Atnip, "there are long stretches on the hillsides with no water." Keep your bottles full by camping along Padfield Branch Creek (mile 6), then at Black River (mile 15.5), and at Taum Sauk Creek (mile 26.5).