My knobby bike tires sputter and skitter along this little stretch of the 100-mile-long Maah Daah Hey Trail, and I can't stop the staccato refrain in my head: "I don't know if I can do this." I've never mountain biked in my life. How did I end up on a run known for its canyon-hugging curves? Ah, I remember now. My friends talked me into it over a dinner of creamy Alfredo pasta at Medora's elegant Rough Riders Hotel.
Maybe it was the restaurant's exquisitely restored pressed-tin ceilings, or the professional servers who hail from around the world, or the perfectly plated food I typically find in towns with populations much bigger than 100, but I felt at home at Theodore's. My companions are North Dakota natives—they work in offices most of the year but feel their spirits soar at glimpses of moonlike canyons foreign to people who live just about anywhere else in the Midwest. A little bike ride led by a spunky 50-something outfitter sounded completely reasonable after a glass of good wine and a crackly crème brûlée.
North Dakotans like to joke that their home is the 50th state, the last on travelers' bucket lists. Medora shines as its biggest draw. A dashing French game hunter settled the town in 1883 and named it for his wife, but its more famous resident became president in 1901. Wild mustangs, bison, elk and pronghorn antelope still roam the national park named for Teddy Roosevelt.
Pictured: Dakota Cyclery Mountain Bike Adventures leads riders along one of the region's most beautiful trails.
All of it waits like a secret four-plus hours north of Mount Rushmore. Along Interstate-94, bales of hay stretch to the horizon until you reach Painted Canyon, the first glimpse of the badlands. There, endless buttes lord over Medora like a watchful father. On one end of town, a visitors center salutes the Mr. Bubble millionaire who rescued Medora from obscurity during the 1960s. On the other, the Burning Hills Amphitheatre's "Medora Musical" entertains with a folksy mix of country tunes, square dancing, Teddy Roosevelt history and Scripture.
The parts that most appeal to me feel a bit more undiscovered. Western Edge Books, Artwork and Music, one of the few businesses in Medora not run by the Theodore Roosevelt Foundation, could entertain me for hours. I don't think I've read about anything Western since high school. But minutes quickly slip by as my feet shuffle across the hardwood floor, pulled between hundreds of titles exploring Native American history, cowboy culture and, eventually, women who blazed trails long before they clinched the right to vote.
Pictured: Painted rock landscapes stretch in every direction.
Down the street, the scent of cedar wafts through the new Cedar Canyon Spa, where facials and massages in dimly lit rooms honor the region with treatment names like the Little Missouri Mud Wrap. A stagecoach ride re-creates the jostling and lore that prairie travelers endured, and the North Dakota Cowboy Hall of Fame displays a beaded leather vest believed to have belonged to Chief Sitting Bull. (A bonus: The gift shop has fringed cowboy vests and butter-soft leather chaps that will fit my 4-year-old son perfectly.)
Just outside town, the Bully Pulpit Golf Course nestles its rivers of fairways among towering rocks. The old Rough Riders Hotel, originally opened in 1884, unveiled its stunning renovation in 2010. Sumptuous beds with crisp, white linens complement the badlands' palette, rich with chocolate browns and soothing greens. The hotel lobby's library invites guests to curl up in leather chairs and read up on Roosevelt history.
Pictured: Cowboy guides share stories of the past during 30-minute rides.
But all of that falls second to the landscape, and I'm eager to see the wildlife. My North Dakota friends take me through the national park's South Unit, regaling me with tales of wild horses, roaming bison and tourists who refuse to stay in the car when buffalo approach. Minutes tick by. Nothing from the scenic overlooks. Nothing along the byway. I come away disappointed, ever the city girl expecting to see animals on cue.
The next morning, we drive 75 miles to the park's North Unit. I look out forlornly at a grassy landscape that seems pretty tame. Our car rolls inside ... and into the middle of a herd of more than 30 bison. We stop. The animals snort and kick at the ground, yanking at tufts of grass and swinging their shaggy heads. Who in their right mind would get out of the car? The nervous energy from my bike ride returns. But I'd conquered that without a spill (and got a pretty sweet photo of myself in a canyon). I fight the urge to roll up my window, grateful for another look at this frontier.
To plan your trip, contact the Theodore Roosevelt Medora Foundation. (800) 633-6721; medora.com . You'll find most destinations on the site. Most attractions run seasonally.
Cedar Canyon Spa This full-service spa across the street from the Rough Rider Hotel offers plenty of pampering for women, men—even horses! (701) 623-1772; cedarcanyonspa.com 
Chateau de Mores State Historic Site (pictured) Tour the 26 rooms of the Medora founder's 1880s home. (701) 623-4355
Dakota Cyclery Jen Morlock will tailor a ride to your comfort level. (888) 321-1218; dakotacyclery.com 
Theodore Roosevelt National Park Some 70,000 acres of painted canyons and grassy hiking trails border Interstate-94 and the Little Missouri River. (701) 623-4466; nps.gov/thro 
Western Edge Books, Artwork and Music Even if you've never read a lick of Western lore, the amazing array of titles in this sprawling shop will pique your curiosity. (701) 623-4345; westernedgebooks.com 
Theodore's (pictured) Fresh flowers garnish the prime rib and seafood at the Rough Riders Hotel. (800) 633-6721
Cowboy Cafe Order up a hot beef sandwich smothered in gravy and served with buttery mashed potatoes. Leave room for banana cream pie. (701) 623-4343
Rough Riders Hotel (pictured) Stay in one of the eight original rooms or in one of the 68 new tower rooms. From $189. (800) 633-6721; medora.com 
Eagle Ridge Lodge Tidy rooms come with quilts on the bed and gas fireplaces. From $185, including dinner and breakfast. (701) 623-2216; eagleridgelodge.com 
(A version of this story appeared in Midwest Living® May/June 2012.)