May is one of the best times to hit the open road in Southeast Montana. Spring sunshine, blooming prairie landscapes, and wide-open highways create the perfect backdrop for unforgettable road trips and scenic adventures.

From charming small towns and outdoor escapes to historic landmarks and hidden gems, Southeast Montana offers countless opportunities to explore at your own pace and make lasting memories along the way.

This season, discover the beauty, history, and wide-open spaces that make Southeast Montana the perfect destination for a spring road trip.

Road Trip One: Scenic Drives and Badlands Beauty

For travelers looking to slow down and enjoy the scenery, this route combines quiet roads, Yellowstone River views, and the dramatic landscapes of eastern Montana’s badlands.

Start in Miles City

Begin your weekend in Miles City with a relaxed morning downtown. Grab brunch, browse local shops, and enjoy the charm of this classic Eastern Montana town before hitting the road.

Stop: Pirogue Island State ParK

Just minutes from downtown Miles City, take a peaceful detour to Pirogue Island State Park.

This 269-acre undeveloped island park sits along the Yellowstone River and offers:

• Quiet walking paths
• Birdwatching opportunities
• River views surrounded by cottonwoods and prairie

It’s the perfect slow-paced stop to stretch your legs and enjoy the quiet beauty of spring in Southeast Montana.

Optional Stop: Terry, Montana

Continue west with a short stop in Terry, a small prairie town known for its welcoming community and proximity to Makoshika’s changing landscape.

Grab a coffee, explore the local streets, and enjoy a glimpse of small-town Montana life.

Scenic Drive to Makoshika State Park

From Miles City, the drive to Glendive and Makoshika State Park takes approximately 1 hour 30 minutes to 1 hour 45 minutes (about 100 miles) depending on stops.

As you approach Glendive, the rolling prairie begins to shift into dramatic badlands formations—an unforgettable transition into Montana’s largest state park.

Explore Makoshika State Park

Spend the afternoon exploring Makoshika’s unique landscape of sandstone formations, fossil beds, and scenic overlooks. Spring is an ideal time to visit, with comfortable temperatures and fewer crowds.

Take a short hike, stop at viewpoints, and enjoy the quiet beauty of the badlands.

Stay the Night

End the day with an overnight stay in Glendive, where comfortable accommodation and quiet evenings offer the perfect close to a scenic Southeast Montana getaway.

Road Trip Two: History, Culture, and Open Roads

For travelers interested in Montana history, cultural landmarks, and iconic landscapes, this route offers a weekend full of discovery.

Begin in Southeast Montana’s Historic Heart

Begin your weekend in Billings, Montana’s largest city and a great launch point for nearby attractions. Explore downtown’s local restaurants, breweries, and shops, or stroll through the historic districts before heading out.

Stop: Pompeys Pillar National Monument

Head east of Billings to Pompeys Pillar National Monument, one of the most significant historical sites in the region.

Here you can:

• See William Clark’s signature carved into the sandstone
• Walk interpretive trails along the Yellowstone River
• Learn about the Lewis and Clark Expedition

Stop: Pictograph Cave State Park

Continue back toward Billings to Pictograph Cave State Park, home to ancient rock art dating back thousands of years.

The short loop trail offers a powerful look into early human history in the region.

Stop: Hardin, Montana

Travel east along I-90 to Hardin, a gateway community near several important cultural and historic sites.

This is a great place to take a break, grab lunch, and experience a classic small Montana town.

Stop: Little Bighorn Battlefield National Monument

Just outside Hardin, explore Little Bighorn Battlefield National Monument, one of the most significant historic sites in the United States.

This solemn and powerful landscape tells the story of the 1876 battle between the U.S. Army’s 7th Cavalry and Lakota, Northern Cheyenne, and Arapaho warriors. Visitors can:

• Drive the battlefield tour road
• Visit memorials and interpretive exhibits
• Walk the scenic hills overlooking the Little Bighorn River

It’s a place of reflection, perspective, and deep historical importance.

Stop: Custer Battlefield Trading Post & Café (“Putt’s”)

After touring Little Bighorn Battlefield National Monument, continue your experience in the heart of Crow Country at the Custer Battlefield Trading Post & Café or as the locals call it, “Putt’s.”

This is a must-stop for both food and culture.

Order the standout Buffalo Burger, made with 100% buffalo meat, grilled and served with classic toppings. Pair it with the sweet potato waffle fries, a local favorite that’s worth the stop on its own.

While you’re there, browse the attached trading post featuring Native American-made goods, or take a moment to appreciate the café interior, filled with colorful beadwork and Native art that reflects the region’s cultural heritage.

Continue Your Journey Through Southeast Montana

From here, travelers can continue exploring nearby Crow Country, return toward Billings, or extend the road trip deeper into Southeast Montana’s wide-open landscapes.

Two Road Trips, Endless Montana Views

From peaceful prairie drives to rugged badlands and historic landmarks, Southeast Montana offers unforgettable weekend adventures in every direction.

Whether you’re exploring scenic state parks, discovering Montana history, or simply enjoying the freedom of the open road, these two road trips showcase some of the best experiences the region has to offer.

Fill the tank, map your route, and discover why Southeast Montana is made for road trips.