There’s something different about Southeast Montana. The roads stretch longer, the skies feel wider, and the stories of cowboys, dinosaurs, railroads, and presidents.

This five-day journey takes you from Billings across the rolling plains of eastern Montana and into the rugged Badlands of North Dakota, ending at the remarkable Theodore Roosevelt Presidential Library. Along the way, you’ll discover quiet towns, rich history, and landscapes that haven’t changed much in generations.

Billings

Start your adventure in Montana’s largest city, where the West meets modern comfort.

Spend your afternoon exploring downtown, where historic buildings house local shops, restaurants, and breweries. For a wider perspective, head up to the Rimrocks, sandstone cliffs that overlook the city and stretch toward the plains you’ll soon be traveling.

If time allows step inside the Moss Mansion, a beautifully preserved home that tells the story of early Montana life.

Settle in for the night, you’re heading east in the morning.

East of Billings → Colstrip (122 miles, 1 hr 48 min)

Leave the city behind and follow the Yellowstone River into open country, where cottonwoods line the water and trains still move goods across the plains.

Optional Stop: Just a short drive east of Billings, Huntley offers a peaceful introduction to Montana's agricultural landscape. Take a moment to enjoy the scenic Yellowstone Valley and experience the quiet charm of one of Southeast Montana's welcoming rural communities.

Then, you’re off to Pompeys Pillar National Monument. Climb to the top and stand beside the signature of William Clark, carved here during the Lewis and Clark Expedition, which is one of the only physical traces left from that journey.

Optional Stop: Continue east to Hysham, a small Yellowstone River community surrounded by rolling hills and fertile farmland. Stretch your legs, explore the downtown area, or simply enjoy the slower pace before continuing your journey across the plains.

Continue east through the small community of Forsyth for a stop on the Burger Trail before arriving in Colstrip, a town shaped by Montana’s energy industry and surrounded by wide-open prairies.

As the sun sets, take in the quiet, this is big sky country at its most peaceful location, especially at Castle Rock Lake.

Day 3: Colstrip → Miles City (80 miles, 1 hr 13 min)

Today’s drive brings you deeper into the culture of the American West.

Arrive in Miles City, a place where cowboy traditions are still part of everyday life. Begin at the Range Riders Museum, where exhibits tell the story of ranching, railroads, and the people who built this region.

Stroll through historic downtown and, if you’re feeling adventurous, step into the legendary Montana Bar, where the past doesn’t feel all that far away.

Depending on the time of year, you might even catch the energy of the Miles City Bucking Horse Sale, the Miles City Ranch Rodeo, or the Miles City PRCA Rodeo, celebrations of rodeo culture that draw visitors from across the country.

Day 4: Miles City → Glendive (76 miles, 1 hr 9 min)

Head east along I-94 toward the badlands.

Optional Stop: Break up the drive with a stop in Terry, a welcoming small town known for its rich railroad history and easy access to Montana's badlands. Stretch your legs with a stroll through downtown, browse local shops, or take a short detour to explore the nearby Terry Badlands, where colorful rock formations and quiet scenic overlooks offer a glimpse of the rugged landscapes that define eastern Montana.

Your destination is Glendive, home to one of Montana’s most unexpected landscapes. Spend your day exploring Makoshika State Park, where dramatic rock formations rise from the earth, and dinosaur fossils tell the story of a world millions of years old.

At the visitor center, you’ll learn how this landscape looked when creatures like Tyrannosaurus rex roamed the region.

Before leaving town, stop at the Glendive Dinosaur and Fossil Museum to see some of the most complete fossil displays in the state.

Day 5: Glendive → Medora (62 miles, 55 min)

Cross the Montana–North Dakota border and watch the landscape shift once again.

Rolling prairie gives way to the colorful buttes and rugged terrain of the Badlands as you approach Medora.

Spend your final day exploring Theodore Roosevelt National Park, where bison roam and scenic drives wind through striking formations. It was here that Theodore Roosevelt found the experiences that helped shape his conservation legacy.

End your journey at the Theodore Roosevelt Presidential Library, a place designed to connect visitors to both the landscape and the ideas that defined one of America’s most influential leaders.