Some roads don’t just take you somewhere, they take you through something. Leaving the painted buttes of western North Dakota behind, this seven-day journey carries you across the wide-open plains of Southeast Montana, where history runs deep, towns feel timeless, and the horizon never seems to end. By the time you reach the geothermal wonders of Yellowstone National Park, you’ll have experienced a quieter, more personal side of the Northern Plains.

Day 1: Medora → Glendive (62 miles, 56 min)

After spending time in Medora exploring Theodore Roosevelt National Park and the Theodore Roosevelt Presidential Library, continue west along I-94 into Southeast Montana. Your first stop is Glendive, a welcoming community nestled along the Yellowstone River and known as the gateway to Montana's badlands.

Start by exploring Glendive's historic downtown, where you'll find local shops, restaurants, and small-town charm. Then head to Makoshika State Park, Montana's largest state park, where dramatic rock formations, scenic overlooks, and ancient fossil beds reveal a landscape shaped over millions of years.

Before ending the day, stop by the Glendive Dinosaur and Fossil Museum to discover impressive dinosaur exhibits and learn more about the prehistoric creatures that once roamed this remarkable corner of Montana.

Head west along I-94 toward Miles City, following a route shaped by the Yellowstone River and the railroads that helped build the region.

Along the way, make an optional stop in Terry and enjoy a bite on the Southeast Montana Burger Trail before continuing your journey. Once you arrive in Miles City, check out additional Burger Trail locations and discover why the region has become a favorite destination for burger lovers.

Spend the afternoon exploring Miles City, Montana's Cowboy Capital. Visit the Range Riders Museum to learn about the area's ranching heritage, then stroll through the historic downtown, where western storefronts, local boutiques, art galleries, and welcoming restaurants celebrate the community's rich western culture and hospitality.

If you're visiting in May, don't miss the legendary Miles City Bucking Horse Sale, one of Montana's most iconic rodeo traditions.

Day 3: Miles City → Baker (80 miles, 1 hr 15 min)

Leave the interstate behind and travel southeast through the wide-open landscapes of Southeast Montana, where quiet highways, rolling prairies, and endless skies create a slower pace of travel.

Make your way toward Baker, a welcoming community surrounded by some of the region's most unique landscapes. Along the way, watch the scenery shift from ranchland to rugged badlands as you approach one of Southeast Montana's most memorable natural treasures.

Near Baker, explore Medicine Rocks State Park, where towering sandstone formations, weathered arches, and centuries-old carvings tell stories of the people who have traveled through this landscape for generations, including Indigenous peoples, early settlers, and Theodore Roosevelt.

Spend the evening exploring Baker's downtown, enjoying local hospitality, and experiencing some of Montana's darkest skies beneath a spectacular blanket of stars.

Day 4: Baker → Ekalaka (36 miles, 38 min)

Continue south to Ekalaka, one of Southeast Montana's most charming and character-filled communities.

Start your visit at the Carter County Museum, home to one of the state's finest collections of dinosaur fossils, archaeological discoveries, and regional artifacts that tell the story of this ancient landscape.

Take time to explore Ekalaka's quiet downtown, nearby public lands, and scenic backroads through the Long Pines, where pine-covered hills and open rangeland create a peaceful contrast to the surrounding prairie.

Enjoy Ekalaka for another unforgettable evening beneath some of Montana's darkest skies.

Day 5: Ekalaka → Hardin (approximately 180 miles, 3 hr 30 min)

Today's journey takes you across the heart of Southeast Montana, where sweeping prairies, ranching communities, and rich Indigenous history come together.

Travel west through Broadus, a welcoming community in the heart of Powder River Country. Take time to explore the town, enjoy a local meal, and experience the hospitality that defines this corner of Montana before continuing along U.S. Highway 212.

As you continue west, pass through Lame Deer, the headquarters of the Northern Cheyenne Nation, where the surrounding landscape reflects the deep cultural heritage of the region.

Your destination is Hardin, the gateway to one of the West's most significant historic sites. Spend the afternoon exploring Little Bighorn Battlefield National Monument, where you can learn about the events of the Battle of the Little Bighorn and the histories of the Lakota, Northern Cheyenne, Arapaho, and the U.S. 7th Cavalry.

After visiting the battlefield, enjoy an evening in Hardin with local dining, shopping, and small-town hospitality.

Day 6: Hardin → Billings (approximately 67 miles, 1 hr)

Begin the day by following the Yellowstone River west toward Billings, with several worthwhile stops along the way.

At Pompeys Pillar National Monument, climb to the top of the sandstone formation and see the signature William Clark left during the Lewis and Clark Expedition in 1806, one of the few remaining physical traces of the journey.

Optional Stop: Learn about the life and legacy of Chief Plenty Coups, the last traditional chief of the Crow Tribe, by exploring his home, historic buildings, and interpretive trails at Montana's only state park dedicated to an American Indian leader.

Optional Stop: Before arriving in Billings, explore Pictograph Cave State Park, where ancient rock paintings and archaeological discoveries provide a fascinating glimpse into more than 2,000 years of human history in the Yellowstone Valley.

Stroll through the vibrant Billings downtown, browse locally owned shops, enjoy regional restaurants and breweries, or take in panoramic views from the Rimrocks before your final night in Southeast Montana.

Day 7: Billings → Yellowstone National Park (140 miles, 3 hr 9 min)

Enjoy one final morning in Southeast Montana before beginning your journey toward Yellowstone National Park.

Take time for breakfast at a local café, visit a museum, explore downtown shops, or enjoy one last view from the Rimrocks before continuing your adventure.

Seasonal Scenic Route: Red Lodge & the Beartooth Highway

When the Beartooth Highway is open seasonally, travel south from Billings through Red Lodge and experience one of America's most spectacular mountain drives. The Beartooth Highway climbs through alpine terrain, revealing snow-capped peaks, glacial lakes, sweeping overlooks, and unforgettable views before arriving at Yellowstone National Park's Northeast Entrance.

Alternate Route: Year-Round Travel

When the Beartooth Highway is closed for the season, continue toward Yellowstone via the Interstate 90 route through Montana's scenic mountain landscapes. While the drive takes you through central Montana, travelers will still experience the beauty of the region's forests, rivers, and changing terrain as they transition from Southeast Montana's wide-open prairie to Yellowstone's iconic wilderness.

No matter the route, this final drive brings your Southeast Montana adventure to a memorable close as you arrive at Yellowstone National Park, where wildlife, geothermal wonders, and some of the country's most dramatic landscapes await.