The Biggest Surprise You’ll Come Across While Hiking This Incredible Trail in North Dakota

I am always on the lookout for hiking trails with unique twists along the way. In my opinion, these unexpected gems make the hike even more exciting. So, when I discovered Point to Point Trail in Medora, North Dakota, I was immediately captivated—and you will be, too. Besides the sweeping views from atop the butte, you’ll come across several surprises on this trek through the badlands. This could arguably be the most unpredictable hiking trail in North Dakota. The coolest part? The trail was inspired by Theodore Roosevelt's favorite game, Point to Point, with one simple rule: Whatever obstacles you encounter, “you must never go around, but always over, under, or through." If you’re ready for this adventure, grab your favorite hiking boots, and let’s go! 

The trailhead is located at Point to Point Park, a small but mighty local park offering mini golf, a zip line, pickleball, and a lazy river. The outdoor playground is one of the newest additions to the Medora community, and it’s a great family-friendly destination for a day trip.

Sure, the park itself is a wonderful space to play, but the hiking trail takes it to another level. At 1.5 miles long, the loop might be short, but don’t underestimate this route; it’s packed with adventure. If you’re afraid of heights, this trail might not be ideal since there are some narrow ridgelines and steep drop-offs as you trek. I wouldn’t recommend it for younger kids either, especially if they’re beginner hikers. Older kids who are avid adventurers should be fine here. Unfortunately, your furry bestie must sit this one out, too. The good news, however, is that this trail doesn’t disappoint.

From the moment you begin your climb, expect spectacular views of the area, and from the top of the butte, it’s simply breathtaking. You’ll see the town of Medora below, panoramic views of the rugged badlands, the Little Missouri River valley, plus Theodore Roosevelt National Park in the distance. 

Not too far on your trek, you’ll come across the most surprising and coolest thing on this trail: a vertical chain ladder embedded in the cliff leading to the top of the butte. If you’re up for the adventure, go for it! Some might think of these steps as an obstacle, but I see them as part of the fun. Will you go around it, or will you face the challenge and go up the ladder? The choice is yours.

Climbing the ladder is the fastest way to the top, so if you can conquer it, it will be extremely rewarding. At the end of the climb, another surprise: You'll find yourself standing at Schafer Point, a historic site with a pavilion, picnic benches, signs, and a small monument. It is at this spot that local businessman and philanthropist Harold Schafer had dreams of improving the town. 

Aside from the ladder, there are several cool overlooks, unique rock formations, and the wildlife is plentiful here. Keep your eyes peeled for prairie dogs, deer, and you might even spot horses along the way. Moreover, the trail is both fun and educational, with interpretive signs about Roosevelt scattered throughout the area. Be sure to stop and read each of them.

If you want even more value from this hike, you can schedule a tour with the local Theodore Roosevelt historian, who will provide more history lessons along the route. Overall, you never know what obstacles or surprises await you on this hike, making it one of the most unpredictable hiking trails in North Dakota. 

Pro Tip: Although the trail is marked, the side trails can be confusing, so I would advise downloading AllTrails+ to help you stay on track. Also, pay attention to the weather as you don’t want to hike this trail if it’s wet and muddy. The steep, narrow ledges can be a hazard.

Have you ever hiked the Point to Point Trail? If so, what did you like the most about it? Tell us on our nomination page. While you’re there, share your favorite hiking trail in North Dakota with us. 

If you’re visiting Medora, check out our article about this charming North Dakota town. Be sure to stop and check out the other attractions here.