Medora, North Dakota
It may be a tiny town that’s home to less than 150 people year-round, but Medora also happens to have the Maah Daah Hey Trail—one of the longest singletrack trails in the U.S.—running right through it. It starts about 30 miles south of town and stretches 144 miles through the state’s Badlands territory, ending in Waterford City. Along the way you can expect plenty of tough climbs up the bentonite buttes, steep descents through the valleys, and you’ll even cross paths with the Little Missouri River in two spots. If you take on the entire trail, there are 11 developed campgrounds for when you need a rest. (You’ll get the best experience spreading this one over multiple days.) If not, there are 16 trailheads with connecting access, so you can join in and jump off wherever you want. Just keep an eye out for wildlife when you’re in the saddle: Plenty have reported sightings of antelope, bighorn sheep, and bison, especially once you cross into Theodore Roosevelt National Park territory.
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